trans-Methyl-2-chlor-2-butenoat

• 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: trans-Methyl-2-chlor-2-butenoat
• 英文别名: E-3-Methyl-2-chloracrylsaeure-methylester；methyl (2E)-2-chloro-2-butenoate；methyl (E)-2-chlorobut-2-enoate
• 化学式: C₅H₇ClO₂
• 分子量: 134.562
• InChiKey: NTMJDABWJARASG-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  erythro 3-bromo-2-chloro-butenoate 在 三乙胺 作用下， 以 正戊烷 为溶剂， 生成 trans-Methyl-2-chlor-2-butenoat
  参考文献：
  名称：

  Effect of a carbonyl group on the ring opening of a neighboring bromonium ion

  摘要：

  DOI：

  10.1021/jo01329a003

文献信息

• Reaction of activated vinyl halides with tervalent phosphorus nucleophiles
  作者：Gerald Pattenden、Brian J. Walker

  DOI：10.1039/j39690000531

  日期：——

  cis- and trans- Isomers of derivatives of 3-halogenoacrylic acids undergo nucleophilic displacement reactions with triphenylphosphine, tri-n-butylphosphine, and triethyl phosphite to produce the correspondingtrans-vinyl-phosphonium salts and -phosphonates exclusively. 1H n.m.r.spectra are reported for these compounds. The mechanism of the displacement reaction is discussed.

  3-卤代丙烯酸衍生物的顺式和反式异构体与三苯基膦，三正丁基膦和亚磷酸三乙酯进行亲核取代反应，仅生成相应的反式-乙烯基-盐和-膦酸酯。据报道这些化合物的1 H nmr光谱。讨论了置换反应的机理。
• Enoate Reductase-Mediated Preparation of Methyl (<i>S</i>)-2-Bromobutanoate, a Useful Key Intermediate for the Synthesis of Chiral Active Pharmaceutical Ingredients
  作者：Elisabetta Brenna、Francesco G. Gatti、Alessia Manfredi、Daniela Monti、Fabio Parmeggiani

  DOI：10.1021/op200086t

  日期：2012.2.17

  Enoate reductases belonging to the Old Yellow Enzyme (OYE) family were employed to develop a biocatalysed approach to methyl (S)-2-bromobutanoate, a key intermediate for the introduction of a particular stereogenic unit into the molecular skeleton of a certain class of chiral drugs. Methyl (Z)-2-bromocrotonate afforded, respectively, (S)-2-bromobutanoic acid (ee = 97%) and methyl (S)-2-bromobutanoate (ee = 97%) by baker's yeast fermentation and by OYE1-3 biotransformations. The bioreductions of other methyl 2-haloalkenoates were also considered. It was observed that the (Z)- and (E)-diastereoisomers of alpha-bromo unsaturated esters afforded the same enantiomer of the corresponding reduced product.
• Effect of a carbonyl group on the ring opening of a neighboring bromonium ion
  作者：Victor L. Heasley、Dan W. Spaite、Dale F. Shellhamer、Gene E. Heasley

  DOI：10.1021/jo01329a003

  日期：1979.7