(S),(E)-Methyl 4-hydroxy-hex-2-enoate | 130323-18-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S),(E)-Methyl 4-hydroxy-hex-2-enoate
• 英文别名: methyl (2E,4S)-4-hydroxy-2-hexenoate；methyl (E,4S)-4-hydroxy-2-hexenoate；methyl (E,4S)-4-hydroxyhex-2-enoate
• CAS: 130323-18-1
• 化学式: C₇H₁₂O₃
• 分子量: 144.17
• InChiKey: OJSUVKLSWRWMJO-OVCGOVNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl (E)-4-hydroxy-2-hexenoate 生成 (S),(E)-Methyl 4-hydroxy-hex-2-enoate
  参考文献：
  名称：

  Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction

  摘要：

  DOI：

  10.1016/s0957-4166(00)86334-x

文献信息

• Asymmetric oxyselenenylation–deselenenylation reactions of alkenes induced by camphor diselenide and ammonium persulfate. A convenient one-pot synthesis of enantiomerically enriched allylic alcohols and ethers
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/s0957-4166(99)00048-8

  日期：1999.2

  The reaction of β,γ-unsaturated esters and nitriles with camphor diselenide and ammonium persulfate in methanol, ethylene glycol or water affords enantiomerically enriched γ-alkoxy or γ-hydroxy α,β-unsaturated derivatives, respectively, in good chemical yields and with moderate to good enantioselectivity.

  β，γ-不饱和酯和腈与樟脑二硒化物和过硫酸铵在甲醇，乙二醇或水中的反应分别得到对映体富集的γ-烷氧基或γ-羟基α，β-不饱和衍生物，化学收率良好，温和良好的对映选择性。
• Optically active building blocks from the SPAC reaction: a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone, a statine analog
  作者：Kevin Burgess、Juanita Cassidy、Ian Henderson

  DOI：10.1021/jo00006a017

  日期：1991.3

  Factors that govern chemical and optical yields of methyl gamma-hydroxy-alpha,beta-unsaturated esters 1 formed in reactions of optically active sulfinylacetates 2 with aldehydes (the ''SPAC'' reaction) are defined. Racemic samples of these chirons (1) can be resolved via acylations mediated by crude preparations of the lipase Pseudomonas K-10 in organic solvents. Combinations of asymmetric SPAC reactions with these biocatalytic resolutions provide routes to highly optically active esters 1 in good yields. This methodology is applied in a completely asymmetric synthesis of (4S-cis)-5-(cyclohexylmethyl)-4-hydroxy-2-pyrrolidinone (15), a cyclic derivative of (3S,4S)-4-amino-5-cyclohexyl-3-hydroxypentanoic acid (ACHPA).
• Enantioselective reduction of γ-hydroperoxy-α,β-unsaturated carbonyl compounds catalyzed by lipid-coated peroxidase in organic solvents
  作者：Hidetaka Nagatomo、Yoh-ichi Matsushita、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.1016/s0957-4166(03)00436-1

  日期：2003.8

  The reduction of racemic gamma-hydroperoxy-alpha,beta-unsaturated carbonyl compounds in the presence of lipid-coated horseradish peroxidase as a homogenious catalyst in organic solvents such as toluene, benzene and chlororform containing a small amount of water enantio selectively afforded optical active (R)-alcohols and (S)-hydroperoxides, respectively. (C) 2003 Elsevier Ltd. All rights reserved.
• BURGESS, KEVIN;CASSIDY, JUANITA;HENDERSON, IAN, J. ORG. CHEM., 56,(1991) N, C. 2050-2058
  作者：BURGESS, KEVIN、CASSIDY, JUANITA、HENDERSON, IAN

  DOI：——

  日期：——
• Asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids by Diels-Alder reaction
  作者：Carlos Cativiela、Pilar López、José A. Mayoral

  DOI：10.1016/s0957-4166(00)86334-x

  日期：1990.1