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N-BOC-L-Prolinal, also known as N-(tert-butoxycarbonyl)-L-proline aldehyde, is an organic compound that serves as a key building block in the synthesis of various complex organic molecules, particularly in the production of norsecurinine-type alkaloids and isaindigotidione carboskeleton.

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  • 69610-41-9 Structure
  • Basic information

    1. Product Name: N-BOC-L-Prolinal
    2. Synonyms: BOC-L-PROLINAL;N-BOC-L-PROLINAL;(S)-tert-Butyl 2-formylpyrrolidine-1-carboxylate;2-Formylpyrrolidine-1-carboxylic acid tert-butyl ester;(S)-N-Boc-pyrrolidine-2-carboxaldehyde, N-(tert-Butoxycarbonyl)-L-prolinal;(S)-N-BOC-Prolinal,97%;N-(Tert-butoxycarbonyl)-L-prol;(S)-1-Boc-2-forMylpyrrolidine
    3. CAS NO:69610-41-9
    4. Molecular Formula: C10H17NO3
    5. Molecular Weight: 199.25
    6. EINECS: 1592732-453-0
    7. Product Categories: Amino Aldehydes;Aldehydes;Amino Acid Derivatives;Building Blocks;C10-C12;Carbonyl Compounds;Chemical Biology;Chemical Synthesis;Organic Building Blocks;Peptide Chemistry;Heterocycles
    8. Mol File: 69610-41-9.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 211 °C(lit.)
    3. Flash Point: 135 °F
    4. Appearance: clear light yellow viscous liquid
    5. Density: 1.063 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 0.00483mmHg at 25°C
    7. Refractive Index: n20/D 1.462(lit.)
    8. Storage Temp.: Store at 0-5°C
    9. Solubility: N/A
    10. PKA: -3.03±0.40(Predicted)
    11. Water Solubility: Slightly soluble water. Soluble in chloroform.
    12. Sensitive: Air Sensitive
    13. CAS DataBase Reference: N-BOC-L-Prolinal(CAS DataBase Reference)
    14. NIST Chemistry Reference: N-BOC-L-Prolinal(69610-41-9)
    15. EPA Substance Registry System: N-BOC-L-Prolinal(69610-41-9)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36
    4. RIDADR: 1989
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: IRRITANT
    8. PackingGroup:
    9. Hazardous Substances Data: 69610-41-9(Hazardous Substances Data)

69610-41-9 Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-L-Prolinal is used as a key building block for the synthesis of norsecurinine-type alkaloids and isaindigotidione carboskeleton, which are important compounds with potential pharmaceutical applications. Its role in the synthesis process is crucial for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
N-BOC-L-Prolinal is used as a versatile intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure allows for selective reactions and functional group manipulations, making it a valuable tool for chemists in the synthesis of target compounds.

Check Digit Verification of cas no

The CAS Registry Mumber 69610-41-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,9,6,1 and 0 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 69610-41:
(7*6)+(6*9)+(5*6)+(4*1)+(3*0)+(2*4)+(1*1)=139
139 % 10 = 9
So 69610-41-9 is a valid CAS Registry Number.
InChI:InChI=1/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h7-8H,4-6H2,1-3H3/t8-/m1/s1

69610-41-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
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  • Alfa Aesar

  • (H26495)  N-Boc-L-prolinal, 96%   

  • 69610-41-9

  • 1g

  • 1416.0CNY

  • Detail
  • Alfa Aesar

  • (H26495)  N-Boc-L-prolinal, 96%   

  • 69610-41-9

  • 5g

  • 4631.0CNY

  • Detail
  • Aldrich

  • (483761)  Boc-L-prolinal  97%

  • 69610-41-9

  • 483761-1G

  • 1,319.76CNY

  • Detail

69610-41-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name N-Boc-L-Prolinal

1.2 Other means of identification

Product number -
Other names tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:69610-41-9 SDS

69610-41-9Downstream Products

69610-41-9Relevant articles and documents

l -Proline as a Valuable Scaffold for the Synthesis of Novel Enantiopure Neonicotinoids Analogs

Bonilla-Landa, Israel,Cuapio-Mu?oz, Ulises,Luna-Hernández, Axel,Reyes-Luna, Alfonso,Rodríguez-Hernández, Alfredo,Ibarra-Juarez, Arturo,Suarez-Mendez, Gabriel,Barrera-Méndez, Felipe,Caram-Salas, Nadia,Enríquez-Medrano, J. Francisco,Díaz De León, Ramón E.,Olivares-Romero, José Luis

, p. 1455 - 1465 (2021/02/16)

In this research, six neonicotinoid analogs derived from l-proline were synthesized, characterized, and evaluated as insecticides against Xyleborus affinis. Most of the target compounds showed good to excellent insecticidal activity. To the best of our knowledge, this is the first report dealing with the use of enantiopure l-proline to get neonicotinoids. These results highlighted the compound 9 as an excellent candidate used as the lead chiral insecticide for future development. Additionally, molecular docking with the receptor and compound 9 was carried out to gain insight into its high activity when compared to dinotefuran. Finally, the neurotoxic evaluation of compound 9 showed lower toxicity than the classic neonicotinoid dinotefuran.

X-ray Structure-Guided Discovery of a Potent, Orally Bioavailable, Dual Human Indoleamine/Tryptophan 2,3-Dioxygenase (hIDO/hTDO) Inhibitor That Shows Activity in a Mouse Model of Parkinson’s Disease

Ning, Xiang-Li,Li, Yu-Zhi,Huo, Cui,Deng, Ji,Gao, Cheng,Zhu, Kai-Rong,Wang, Miao,Wu, Yu-Xiang,Yu, Jun-Lin,Ren, Ya-Li,Luo, Zong-Yuan,Li, Gen,Chen, Yang,Wang, Si-Yao,Peng, Cheng,Yang, Ling-Ling,Wang, Zhou-Yu,Wu, Yong,Qian, Shan,Li, Guo-Bo

, p. 8303 - 8332 (2021/06/30)

Human indoleamine 2,3-dioxygenase 1 (hIDO1) and tryptophan 2,3-dioxygenase (hTDO) have been closely linked to the pathogenesis of Parkinson’s disease (PD); nevertheless, development of dual hIDO1 and hTDO inhibitors to evaluate their potential efficacy against PD is still lacking. Here, we report biochemical, biophysical, and computational analyses revealing that 1H-indazole-4-amines inhibit both hIDO1 and hTDO by a mechanism involving direct coordination with the heme ferrous and ferric states. Crystal structure-guided optimization led to23, which manifested IC50values of 0.64 and 0.04 μM to hIDO1 and hTDO, respectively, and had good pharmacokinetic properties and brain penetration in mice.23showed efficacy against the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced mouse motor coordination deficits, comparable to Madopar, an anti-PD medicine. Further studies revealed that different from Madopar,23likely has specific anti-PD mechanisms involving lowering IDO1 expression, alleviating dopaminergic neurodegeneration, reducing inflammatory cytokines and quinolinic acid in mouse brain, and increasing kynurenic acid in mouse blood.

Formal Fluorinative Ring Opening of 2-Benzoylpyrrolidines Utilizing [1,2]-Phospha-Brook Rearrangement for Synthesis of 2-Aryl-3-fluoropiperidines

Kondoh, Azusa,Ojima, Rihaku,Terada, Masahiro

, p. 7894 - 7899 (2021/10/20)

A ring expansion of 2-benzoylpyrrolidines, which involves the formal fluorinative ring opening utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis and a subsequent intramolecular reductive amination, was developed. The operationally simple three-step protocol provides an efficient access to 2-aryl-3-fluoropiperidines. The methodology was further applied to the syntheses of azepanes and tetrahydroquinolines.

Larger scale Stahl oxidation with instant Cu removal in convenient synthesis of chiral bidentate N–heterocyclic carbene precursor

Grudzień, Krzysztof,Noga?, Wojciech,Szczepaniak, Grzegorz,Grela, Karol

, (2021/02/26)

Commercially available N-Boc protected L-proline can be efficiently converted into a chiral, bidentate, aminoalkyl N-heterocyclic carbene ligand precursor in high yield (50% total after 4 steps) without column chromatography purification at any moment. The developed synthetic path includes: (1) redox step leading to an aldehyde, (2) imine condensation and in situ reduction to 1,2-diamine; (3) heterocyclization; (3) removal of the protecting group. Instant separation of Cu traces after the key Stahl oxidation at gram-scale was facilitated by the use of bis(isocyanide) scavenger, SnatchCat, forming insoluble, easy to remove RNC:→[Cu] complexes that allowed usto obtain crude intermediate suitably pure for next steps without tedious purification.

NOVEL CONNECTED BODY AND USE THEREOF IN SPECIFIC CONJUGATION BETWEEN BIOMOLECULE AND DRUG

-

, (2021/05/14)

PROBLEM TO BE SOLVED: To provide: a method for producing a connected body; a method for using the connected body in the production of a uniform conjugate; and a method for applying the conjugate in the treatment of cancer, infectious diseases, and autoimmune diseases. SOLUTION: A novel connected body is provided that includes a 2,3-di-substituted succinic acid group or a 2-mono-substituted or 2,3-di-substituted fumaric acid or maleic acid (trans (E)- or cis (Z)-butenedioic acid) group for conjugating 2 or more compounds/cytotoxic agents per connected body with a cell-binding molecule by specifically bridge-linking to a pair of thiol on the cell-binding molecule. The connected body is exemplified by the following general formula. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT

POTENT HUMAN NEURONAL NITRIC OXIDE SYNTHASE INHIBITORS

-

Paragraph 00355; 00356, (2021/09/04)

Disclosed are 2-aminopyridine derivative compounds for use as inhibitors of nitric oxide synthase (NOS). In particular, the field of the invention relates to 2-aminopyridine derivative compounds for use as inhibitors of neuronal nitric oxide synthase (nNOS), which are formulated as pharmaceutical compositions for treating diseases and disorders associated with nNOS such as Alzheimer's, Parkinson's, and Huntington's diseases, and amytrophic lateral sclerosis, cerebral palsy, stroke/ischemic brain damage, and migraine headaches.

CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP

-

, (2020/05/19)

Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.

AZAARYL DERIVATIVE, PREPARATION METHOD THEREFOR, AND APPLICATION THEREOF FOR USE IN PHARMACY

-

Paragraph 0116-0117, (2020/04/21)

An azaaryl derivative with the structure of formula (I), a preparation method therefor and a pharmaceutical use thereof are disclosed in the present invention. The series of compounds of the present invention can be widely applied in the preparation of dr

A One-Pot Iodo-Cyclization/Transition Metal-Catalyzed Cross-Coupling Sequence: Synthesis of Substituted Oxazolidin-2-ones from N-Boc-allylamines

Chaumont-Olive, Pauline,Cossy, Janine

supporting information, (2020/05/14)

A one-pot iodo-cyclization/transition metal-catalyzed cross-coupling sequence is reported to access various C5-functionalized oxazolidin-2-ones from unsaturated N-Boc-allylamines. Depending on the Grignard reagents used for the cross-coupling, e.g., aryl- or cyclopropylmagnesium bromide, a cobalt or copper catalyst has to be used to obtain the functionalized oxazolidin-2-ones in good yields.

NOVEL POTASSIUM CHANNEL INHIBITORS

-

Page/Page column 56; 73, (2020/10/20)

The present invention relates to novel compounds, pharmaceutical compositions comprising such compounds and their use for treating, alleviating or preventing diseases or disorders relating to the activity of potassium channels.

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