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(R)-(-)-PENTEN-2-OL, also known as (R)-2-Penten-1-ol, is an organic compound with the molecular formula C5H10O. It is a chiral secondary alcohol, characterized by its distinct (R) configuration at the chiral center. (R)-(-)-PENTEN-2-OL is a colorless liquid with a distinctive odor and is soluble in water and various organic solvents. It is an important building block in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries.

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  • 64584-92-5 Structure
  • Basic information

    1. Product Name: (R)-(-)-PENTEN-2-OL
    2. Synonyms: (R)-(-)-2-HYDROXYPENT-4-ENE;(R)-(-)-PENTEN-2-OL;(r)-(-)-4-penten-2-ol;(1R)-1-Methyl-3-butene-1-ol;(2R)-4-Pentene-2-ol;(2R)-pent-4-en-2-ol
    3. CAS NO:64584-92-5
    4. Molecular Formula: C5H10O
    5. Molecular Weight: 86.13
    6. EINECS: N/A
    7. Product Categories: API intermediates;Alcohols;Chiral Building Blocks;Organic Building Blocks
    8. Mol File: 64584-92-5.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 115-116 °C(lit.)
    3. Flash Point: 78 °F
    4. Appearance: /
    5. Density: 0.837 g/mL at 25 °C(lit.)
    6. Refractive Index: n20/D 1.4240(lit.)
    7. Storage Temp.: N/A
    8. Solubility: N/A
    9. PKA: 15.10±0.20(Predicted)
    10. Water Solubility: Soluble in water, 4.526 mg/L @ 25°C.
    11. CAS DataBase Reference: (R)-(-)-PENTEN-2-OL(CAS DataBase Reference)
    12. NIST Chemistry Reference: (R)-(-)-PENTEN-2-OL(64584-92-5)
    13. EPA Substance Registry System: (R)-(-)-PENTEN-2-OL(64584-92-5)
  • Safety Data

    1. Hazard Codes: H226
    2. Statements: 10
    3. Safety Statements: N/A
    4. RIDADR: UN 1987 3/PG 3
    5. WGK Germany: 3
    6. RTECS:
    7. HazardClass: 3
    8. PackingGroup: III
    9. Hazardous Substances Data: 64584-92-5(Hazardous Substances Data)

64584-92-5 Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-PENTEN-2-OL is used as a reactant in the synthesis of aigialomycin D and its analogs, which are known to inhibit protein kinases related to cancer pathways. These compounds have potential applications in the development of novel anticancer drugs, targeting the specific protein kinases that play a crucial role in the growth and progression of cancer cells.
In the synthesis of aigialomycin D and its analogs, (R)-(-)-PENTEN-2-OL serves as a key intermediate, providing the necessary structural framework for the formation of the final product. (R)-(-)-PENTEN-2-OL's unique (R) configuration at the chiral center is essential for the biological activity of the synthesized compounds, as it ensures the correct stereochemistry for effective binding to the target protein kinases.
Furthermore, (R)-(-)-PENTEN-2-OL can be used as a starting material for the synthesis of other bioactive compounds with potential applications in the pharmaceutical industry. Its versatility as a building block allows for the development of a wide range of molecules with diverse biological activities, including those with potential therapeutic benefits.

Check Digit Verification of cas no

The CAS Registry Mumber 64584-92-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,4,5,8 and 4 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 64584-92:
(7*6)+(6*4)+(5*5)+(4*8)+(3*4)+(2*9)+(1*2)=155
155 % 10 = 5
So 64584-92-5 is a valid CAS Registry Number.

64584-92-5 Well-known Company Product Price

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  • Alfa Aesar

  • (B25659)  (R)-(-)-4-Penten-2-ol, 95%   

  • 64584-92-5

  • 1g

  • 1454.0CNY

  • Detail
  • Alfa Aesar

  • (B25659)  (R)-(-)-4-Penten-2-ol, 95%   

  • 64584-92-5

  • 5g

  • 5080.0CNY

  • Detail
  • Aldrich

  • (558036)  (R)-(−)-4-Penten-2-ol  95%

  • 64584-92-5

  • 558036-1G

  • 1,316.25CNY

  • Detail
  • Aldrich

  • (558036)  (R)-(−)-4-Penten-2-ol  95%

  • 64584-92-5

  • 558036-5G

  • 5,536.44CNY

  • Detail

64584-92-5SDS

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 (2R)-pent-4-en-2-ol

1.2 Other means of identification

Product number -
Other names (R)-(-)-4-Penten-2-ol

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:64584-92-5 SDS

64584-92-5Relevant articles and documents

Asymmetric synthesis of (+)-stagonolide C and (-)-aspinolide A via organocatalysis

Shelke, Anil M.,Rawat, Varun,Suryavanshi, Gurunath,Sudalai, Arumugam

, p. 1534 - 1541 (2012)

A new enantioselective synthesis of two important fungal metabolites, (+)-stagonolide C and (-)-aspinolide A, has been described from readily available raw materials. Proline catalyzed asymmetric α-aminooxylation and Jorgensen's epoxidation of aldehydes a

Concise and protecting group-free synthesis of botryolide-E

Chandra Rao,Kumar Reddy,Shekhar,Venkateswarlu

, p. 828 - 829 (2013)

A simple highly concise protective group-free synthesis of botryolide-E from (R)-propylene oxide was developed using Hoveyda Grubbs cross metathesis, Still's modified Horner-Wadsworth-Emmons reaction, and Sharpless asymmetric dihydroxylation, as key steps.

Total synthesis of (–)-cephalosporolide D

Kalavakuntla, Chiranjeevi,Kummari, Vijaya Babu,Yadav, Jhillu Singh

, (2021/03/22)

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

Kim, Minjae,Park, Bohyun,Shin, Minkyeong,Kim, Suyeon,Kim, Junghoon,Baik, Mu-Hyun,Cho, Seung Hwan

supporting information, p. 1069 - 1077 (2021/01/25)

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

A Unified Synthetic Approach to Optically Pure Curvularin-Type Metabolites

Allu, Srinivasa Rao,Banne, Sreenivas,Jiang, Jia,Qi, Na,Guo, Jian,He, Yun

, p. 7227 - 7237 (2019/06/07)

A unified and concise approach to the synthesis of nine curvularin-type metabolites and two analogues has been developed with few steps and high yields. Among them, sumalactones A-D were synthesized for the first time. The key steps in this approach inclu

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

Gn?gi, Lars,Martz, Severin Vital,Meyer, Daniel,Sch?rer, Robin Marc,Renaud, Philippe

supporting information, p. 11646 - 11649 (2019/08/30)

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

A facile, efficient and selective deprotection of p-methoxy benzyl ethers using zinc (Ii) trifluoromethanesulfonate

Chandrasekhar, Choragudi,Rao, Mannam Subba,Sireesha, Reddymasu,Sreenivasulu, Reddymasu

, p. 955 - 958 (2019/11/22)

Deprotection is significant and conducted over mild reaction conditions, in order to restrict any more side reactions with sensitive functional groups as well as racemization or epimerization of stereo center because the protective groups are often cleaved at last stage in the synthesis. P-Methoxy benzyl (PMB) ether appears unique due to its easy introduction and removal than the other benzyl ether protecting groups. A facile, efficient and highly selective cleavage of P-methoxy benzyl ethers was reported by using 20 mole% Zinc (II) Trifluoromethanesulfonate at room temperature in acetonitrile solvent over 15-120 min. time period. To study the generality of this methodology, several PMB ethers were prepared from a variety of substrates having different protecting groups and subjected to deprotection of PMB ethers using Zn(OTf)2 in acetonitrile. In this methodology, zinc triflate cleaves only PMB ethers without affecting acid sensitivity, base sensitivity and also chiral epoxide groups.

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

Yan, Lu,Meng, Yan,Haeffner, Fredrik,Leon, Robert M.,Crockett, Michael P.,Morken, James P.

supporting information, p. 3663 - 3673 (2018/03/21)

A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

Synthesis and Stereochemical Assignment of Arenolide

Liu, Xun,Sun, Chunrui,Mlynarski, Scott,Morken, James P.

supporting information, p. 1898 - 1901 (2018/04/16)

The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.

[1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof

-

Paragraph 0136-0138; 0140; 0142, (2018/04/21)

The invention relates to [1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof, and belongs to the field of BACE (beta-site amyloid precursor protein cleavingenzyme) inhibitors. The [1,3]thiazid-2-amine compounds are compounds, pharmaceutically acceptable salts, stereoisomers, solvates, or prodrugs represented by a formula (I), and the formula (I) is shownin the description. The [1,3]thiazin-2-amine compounds provided by the invention have good inhibiting effects on BACE, and can be used for the preparation of medicines for treating neurodegenerativediseases such as alzheimer diseases.

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