(S),(E)-Methyl 4-Hydroxyhept-2-enoate | 106426-92-0

• 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-Hydroxyhept-2-enoate
• 英文别名: methyl (E,4S)-4-hydroxyhept-2-enoate
• CAS: 106426-92-0
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: NDKPTQNRFWJELN-XPPMVYLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.88
• 重原子数：
  11.0
• 可旋转键数：
  4.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  正戊醛 在 哌啶 作用下， 以 乙腈 为溶剂， 生成 (S),(E)-Methyl 4-Hydroxyhept-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

• A facile route to homochiral sulfoxides
  作者：Kevin Burgess、Ian Henderson

  DOI：10.1016/s0040-4039(01)80467-6

  日期：1989.1

  Biocatalytic resolutions of methyl sulfinylacetates fford sulfoxides (R)-(1) - (6) in very high optical yields; the products have been used in a systematic study of the “SPAC” reaction, an asymmetric synthesis of γ-hydroxy-α,β-unsaturated esters.

  以非常高的光学收率得到亚甲基乙酸乙酸甲酯和亚砜（R）-（1）-（6）的生物催化拆分；该产品已用于系统研究“ SPAC”反应，即不对称合成γ-羟基-α，β-不饱和酯。
• Highly enantioselective rearrangement of (S)-E-α-p-tolysulphinyl-α,β-enoates to (R)-E-γ-hydroxy-α,β-enoates
  作者：Hiroshi Kosugi、Masaki Kitaoka、Akira Takahashi、Hisashi Uda

  DOI：10.1039/c39860001268

  日期：——

  On treatment with pyridine–camphorsulphonic acid, (S)-E-α-p-tolysulphinyl-α-β-enoates (4) undergo enantio-selectively a sequential prototropic shift and allylic sulphoxide–sulphenate rearrangement to produce (R)-E-γ-hydroxy-α,β-enoates (2) in 64–72% optical purity.

  上与吡啶樟脑磺酸，（治疗小号） - ë -α- p -tolysulphinyl-α-β-enoates（4）经历对映选择性地顺序移位的质子和烯丙基亚砜-sulphenate重排以产生（- [R ） - ë - γ-羟基-α，β-烯酸酯（2）的光学纯度为64-72％。
• 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).
• 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：——