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  • 119463-16-0 Structure
  • Basic information

    1. Product Name: preussin
    2. Synonyms: preussin;1-Methyl-5-nonyl-2-(phenylmethyl)-3-pyrrolidinol;L-657398
    3. CAS NO:119463-16-0
    4. Molecular Formula: C21H35NO
    5. Molecular Weight: 317.5087
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 119463-16-0.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 432.1°Cat760mmHg
    3. Flash Point: 11.1°C
    4. Appearance: /
    5. Density: 0.967g/cm3
    6. Vapor Pressure: 3.1E-08mmHg at 25°C
    7. Refractive Index: 1.516
    8. Storage Temp.: N/A
    9. Solubility: N/A
    10. PKA: 14.95±0.60(Predicted)
    11. CAS DataBase Reference: preussin(CAS DataBase Reference)
    12. NIST Chemistry Reference: preussin(119463-16-0)
    13. EPA Substance Registry System: preussin(119463-16-0)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 119463-16-0(Hazardous Substances Data)

119463-16-0 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 119463-16-0 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,9,4,6 and 3 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 119463-16:
(8*1)+(7*1)+(6*9)+(5*4)+(4*6)+(3*3)+(2*1)+(1*6)=130
130 % 10 = 0
So 119463-16-0 is a valid CAS Registry Number.
InChI:InChI=1/C21H35NO/c1-3-4-5-6-7-8-12-15-19-17-21(23)20(22(19)2)16-18-13-10-9-11-14-18/h9-11,13-14,19-21,23H,3-8,12,15-17H2,1-2H3

119463-16-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-benzyl-1-methyl-5-nonylpyrrolidin-3-ol

1.2 Other means of identification

Product number -
Other names Preussin

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:119463-16-0 SDS

119463-16-0Downstream Products

119463-16-0Relevant articles and documents

Molecular Iodine-Mediated α-C-H Oxidation of Pyrrolidines to N,O-Acetals: Synthesis of (±)-Preussin by Late-Stage 2,5-Difunctionalizations of Pyrrolidine

Rong, Hao-Jie,Yao, Jun-Jun,Li, Ji-Kun,Qu, Jin

, p. 5557 - 5565 (2017)

We previously reported an iterative synthesis of unsymmetrical 2,5-disubstituted pyrrolidines from pyrrolidine by two rounds of redox-triggered α-C-H functionalization. Although this approach can be used to introduce substituents at the 2- and 5-positions, it is lengthy because the redox auxiliary must be removed and then reinstalled. Therefore, we sought to develop a method to oxidize 2-functionalized pyrrolidine to cyclic N,O-acetal which could then react with a nucleophile for introduction of the 5-substituent. In this work, we found that molecular iodine can mediate the preferential oxidation of secondary over tertiary α-C-H bonds of α-substituted pyrrolidines to form cyclic N,O-acetals, improving the step economy of our previously reported method. With this strategy, (±)-preussin and its C(3) epimer were synthesized from (±)-pyrrolidin-3-ol.

Alkoxyallene-based syntheses of preussin and its analogs and their cytotoxicity

Hausherr, Arndt,Siemeister, Gerhard,Reissig, Hans-Ulrich

, p. 122 - 134 (2019)

Short syntheses of oxa-preussin, racemic preussin and (-)-preussin are reported. Starting from a racemic 3-nonyl-substituted methoxyallene derivative, its lithiation and addition to phenylethanal provided the corresponding allenyl alcohol that was converted into two diastereomeric dihydrofuran derivatives by silver nitrate-catalyzed 5-endo-trig cyclization. The acid hydrolysis of the enol ether moiety gave heterocyclic ketones and subsequent highly stereoselective reductions with l-selectride furnished 2-benzyl-5-nonylfuran-3-ol derivatives in good overall yield. The major all-cis-diastereomer has the skeleton and relative configuration of preussin and is hence called oxa-preussin. An analogous sequence with the same allene, but an N-sulfonyl imine as the electrophile, finally led to racemic preussin. The stereoselectivities of the individual steps are discussed in detail. With an enantiopure 2-benzyl-5-nonylpyrrolidin-3-one intermediate the preparation of (-)-preussin with an enantiomeric ratio of >95:5 could be accomplished in a few steps. The sign of the optical rotation of this product finally proved the absolute configurations of its precursors and demonstrated that our chiral auxiliary-based route led to the antipode of the natural product. The cytotoxicity of several of the prepared heterocycles against MCF-7 tumor cells was investigated and five compounds, including racemic and enantiopure (-)-preussin, were identified as highly cytotoxic with IC50 values in the range of 3-6 μM.

A concise and efficient synthesis of (+)-preussin

Arevalo-Garcia, Enzo B.

, p. 47 - 50 (2014)

A novel and efficient synthesis of (+)-preussin (7) starting from N-butoxycarbonyl-L-phenylalaninal (1) is described. This natural product was synthesized under mild conditions and with good overall yield.

An efficient approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones through a stereoselective tandem Barbier process: divergent syntheses of (3R,4S)-statines, (+)-preussin and (?)-hapalosin

Si, Chang-Mei,Shao, Lu-Ping,Mao, Zhuo-Ya,Zhou, Wen,Wei, Bang-Guo

, p. 649 - 661 (2017/01/25)

A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P1 = TBS, P2 = H) has been developed through a stereoselective tandem Barbier process of (R,SRS)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.

Asymmetric synthesis of 2,5-disubstituted 3-hydroxypyrrolidines based on stereodivergent intramolecular iridium-catalyzed allylic aminations

Natori, Yoshihiro,Kikuchi, Shunsuke,Kondo, Takahiro,Saito, Yukako,Yoshimura, Yuichi,Takahata, Hiroki

, p. 1983 - 1994 (2014/03/21)

Intramolecular iridium-catalyzed allylic aminations of homochiral (E)-6-N-nosylaminohept-2-en-1-yl methyl carbonates were investigated. The relative position of the 2,5-substituents of the resulting pyrrolidines was found to be controlled by using both enantiomers (4 and 5) of the appropriate chiral ligand, demonstrating a simple and highly stereodivergent synthetic protocol. Selected trans- and cis-2,5-disubstituted 3-hydroxypyrrolidines (2a and 18a) were converted to (+)-bulgecinine (6) and (+)-preussin (7), respectively.

Three-step synthesis of (±)-preussin from decanal

Rosset, Isac G.,Dias, Rafael M. P.,Pinho, Vagner D.,Burtoloso, Antonio C. B.

, p. 6748 - 6753 (2014/08/05)

A straightforward and stereoselective synthesis of the alkaloid preussin is described starting from decanal and diethyl 3-diazo-2-oxopropylphosphonate. The key steps are an aza-Michael reaction from an α,β-unsaturated diazoketone followed by a highly stereoselective Cu-catalyzed ylide formation and then a [1,2]-Stevens rearrangement. This strategy is feasible for extension to preussin analogues, demonstrating its utility for the rapid construction of all-cis-substituted pyrrolidines.

An efficient method for the preparation of 3-hydroxyl-5-substituted 2-pyrrolidones and application in the divergent synthesis of (-)-preussin and its analogues

Zhou, Qian-Ru,Wei, Xiao-Yun,Li, You-Qin,Huang, Danfeng,Wei, Bang-Guo

, p. 4799 - 4808 (2014/06/24)

An asymmetric method to (S,R)-α-hydroxyl-γ-amino alcohols 12 through a diastereoselective addition of Grignard reagents to β-chiral aldimines 11 is described. Subsequent oxidation/cyclization with Sarett reagent provided a novel approach to lactams 14, a flexible building block whose utility was demonstrated in the divergent synthesis of antifungal agent (-)-preussin 5 and its three analogues 23, 24, 25.

Versatile one-pot reductive alkylation of lactams/amides via amide activation: Application to the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (-)-cassine

Xiao, Kai-Jiong,Wang, Yu,Ye, Ke-Yin,Huang, Pei-Qiang

supporting information; experimental part, p. 12792 - 12796 (2011/02/22)

Direct entry: One-pot reductive alkylation of lactams/amides with Grignard reagents has been realized via lactam/amide activation with Tf2O. This method opens a direct entry to α-alkylated amines. The versatility of the method is illustrated by the concise syntheses of bioactive alkaloids (±)-bgugaine, (±)-coniine, (+)-preussin, and (?)-cassine.

A concise and stereoselective synthesis of hydroxypyrrolidines: Rapid synthesis of (+)-preussin

Draper, Jason A.,Britton, Robert

supporting information; experimental part, p. 4034 - 4037 (2010/11/05)

A convergent and stereoselective synthesis of 2,5-disubstituted 3-hydroxypyrrolidines has been developed that involves reductive annulation of β-iminochlorohydrins, which are readily available from β- ketochlorohydrins, and provides rapid access to a variety of 2,5-syn-pyrrolidines. Application of this process to the concise (three-step) synthesis of the fungal metabolite (+)-preussin and analogues of this substance is reported.

Asymmetric synthesis of cis- and trans-2,5-disubstituted pyrrolidines from 3-oxo pyrrolidine 2-phosphonates: Synthesis of (+)-preussin and analogs

Davis, Franklin A.,Zhang, Junyi,Qiu, Hui,Wu, Yongzhong

body text, p. 1433 - 1436 (2009/04/10)

(Chemical Equation Presented) Pyrrolidine enones, derived from 3-oxo pyrrolidine 2-phosphonates and a HWE reaction with aldehydes, on Luche reduction give pyrrolidine allylic alcohols. The alcohols on hydrogenation (Pd/H 2) give cis-2,5-disubstituted pyrrolidines and on treatment with TFA-NaBH3CN undergo a hydroxy directed reduction to trans-2,5-disubstituted pyrrolidines.

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