(R),(E)-Methyl 4-Hydroxyhept-2-enoate | 106426-91-9

• 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-Hydroxyhept-2-enoate
• 英文别名: Methyl (4R)-4-hydroxyhept-2(E)-enoate；2-Heptenoic acid, 4-hydroxy-, methyl ester, [R-(E)]-；methyl (E,4R)-4-hydroxyhept-2-enoate
• CAS: 106426-91-9
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: NDKPTQNRFWJELN-WEWAHIQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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-Hydroxyhept-2-enoate 在 sodium hydroxide 、 phosphate buffer 作用下， 反应 0.5h， 以100%的产率得到(E)-(R)-4-Hydroxy-hept-2-enoic acid
  参考文献：
  名称：

  通过外消旋酯的不对称水解制备（R）-和（S）-（E）-4-羟基-2-不饱和酸

  摘要：

  通过猪胰脂肪酶和对映体的对映选择性水解，由相应的外消旋甲基酯制备了几种光学活性的（R）-和（S）-（E）-4-羟基烷-2-烯酸，它们是脂质过氧化生物活性化合物的代谢物。猪肝酯酶。

  DOI：

  10.1016/s0957-4166(00)80324-9
• 作为产物：
  描述：

  (2S,3S)-(-)-3-丙基环氧乙烷甲醇 在 titanium(IV) isopropylate 、 sodium periodate 、 sodium hydride 、 四丁基高碘酸铵 作用下， 以 四氢呋喃 、 甲醇 、 水 、 paraffin 为溶剂， 反应 9.25h， 生成 (R),(E)-Methyl 4-Hydroxyhept-2-enoate
  参考文献：
  名称：

  Stereoselective Synthesis of Highly Substituted .gamma.-Lactones and Butenolides by Intramolecular Michael Addition of Enantiomerically Enriched .gamma.-[(Phenylthio)acyl]oxy .alpha.,.beta.-Unsaturated Esters

  摘要：

  The synthesis of polysubstituted gamma-lactones by the base-induced cyclization of enantiomerically enriched gamma-((phenylthio)acyl)oxy alpha,beta-unsaturated esters obtained from 2,3-epoxy alcohols is described. The procedure is highly stereoselective and compatible with a wide range of functionalities (ester, tetrahydropyranyl ether, silyl ether, etc.). Varying degrees of substitution, including quaternary centers, in the final gamma-lactone were synthesized with excellent stereoselectivity. Useful functional interconversions were successfully demonstrated, in particular those resulting in butenolides. By the use of AM1 it was concluded that the intramolecular Michael reaction can be described as a kinetically controlled reaction in which the relative stability of the transition states for all possible final configurations led to geometries in agreement with the experimental results.

  DOI：

  10.1021/jo00095a022

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：——
• Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S., J. Org. Chem, 59 (1994) N 16, S 4461-4472
  作者：Rodriguez Carmen M., Martin Tomas, Ramirez Miguel A., Martin iVictor S.

  DOI：——

  日期：——