(R)-(E)-Methyl 4-hydroxypent-2-enoate | 124818-73-1

• 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: (R)-(E)-Methyl 4-hydroxypent-2-enoate
• 英文别名: methyl (E,4R)-4-hydroxypent-2-enoate
• CAS: 124818-73-1
• 化学式: C₆H₁₀O₃
• 分子量: 130.144
• InChiKey: SUMCTISXZSKAKN-QLSVQJPWSA-N

物化性质

• 沸点：
  206.5±23.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(E)-Methyl 4-hydroxypent-2-enoate 在 palladium on activated charcoal 氢气 、 4-甲基苯磺酸吡啶 作用下， 生成 (R)-5-甲基二氢呋喃-2-酮
  参考文献：
  名称：

  Kinetic resolution of racemic β,γ-epoxy esters with pig liver esterase (PLE, e.c. 3.1.1.1.)

  摘要：

  DOI：

  10.1016/s0040-4039(01)80438-x
• 作为产物：
  描述：

  ((2R,3S)-3-Methyl-oxiranyl)-acetic acid methyl ester 在 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 生成 (R)-(E)-Methyl 4-hydroxypent-2-enoate
  参考文献：
  名称：

  Kinetic resolution of racemic β,γ-epoxy esters with pig liver esterase (PLE, e.c. 3.1.1.1.)

  摘要：

  DOI：

  10.1016/s0040-4039(01)80438-x

文献信息

• A Four-Step Route from Aldehydes to C₂-Elongated Enantiomerically Pure <i>α</i>,<i>β</i>-Unsaturated <i>γ</i>-Hydroxy Esters
  作者：Christian Harcken、Reinhard Brückner

  DOI：10.1055/s-2001-13372

  日期：——

  Asymmetric dihydroxylation of β,γ-unsaturated esters 4 provided β-hydroxy-γ-lactones 3 or ent-3. Methanolysis acetonide formation and LDA-mediated fragmentation of the resulting esters 5/ent-5 furnished the γ-chiral acrylates 6/ent-6 containing disubstituted C=C bonds (93-99% ee). Also, β-hydroxy-γ-lactones ent-3 a and 3 b were α-butylated and α-brominated, respectively, prior to methanolysis, acetonide formation, and fragmentation which led to the γ-chiral acrylates 9 and 12 with trisubstituted C=C bonds (94 and 95% ee, respectively).

  β,γ-不饱和酯4 的不对称二羟基化提供β-羟基-γ-内酯3 或ent-3。甲醇分解丙酮化物的形成和所得酯5/ent-5 的LDA 介导的断裂提供了含有双取代C=C 键（93-99% ee）的γ-手性丙烯酸酯6/ent-6。此外，β-羟基-γ-内酯 ent-3 a 和 3 b 分别在甲醇解、丙酮化物形成和裂解之前进行 α-丁基化和 α-溴化，从而产生 γ-手性丙烯酸酯 9 和 12三取代的 C=C 键（分别为 94% 和 95% ee）。
• 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：——