methyl (Z)-3-chloro-2-octenoate

• 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: methyl (Z)-3-chloro-2-octenoate
• 英文别名: (Z)-methyl 3-chlorooct-2-enoate；methyl 3-chlorooct-2-enoate；3-chloro-oct-2-enoic acid methyl ester；3-Chlor-oct-2-ensaeure-methylester；methyl (Z)-3-chlorooct-2-enoate
• 化学式: C₉H₁₅ClO₂
• 分子量: 190.67
• InChiKey: IXHLPTMNQDZVDS-FPLPWBNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  sodium,hept-1-yne 在 盐酸 作用下， 生成 methyl (Z)-3-chloro-2-octenoate
  参考文献：
  名称：

  Moureu; Delange, Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1901, vol. 132, p. 989

  摘要：

  DOI：

文献信息

• Iridium‐Catalyzed Hydrochlorination and Hydrobromination of Alkynes by Shuttle Catalysis
  作者：Peng Yu、Alessandro Bismuto、Bill Morandi

  DOI：10.1002/anie.201912803

  日期：2020.2.10

  Described herein are two different methods for the synthesis of vinyl halides by a shuttle catalysis based iridium-catalyzed transfer hydrohalogenation of unactivated alkynes. The use of 4-chlorobutan-2-one or tert-butyl halide as donors of hydrogen halides allows this transformation in the absence of corrosive reagents, such as hydrogen halides or acid chlorides, thus largely improving the functional-group

  本文描述了通过未活化炔烃的基于铱催化的转移氢卤化的穿梭催化来合成卤乙烯的两种不同方法。使用 4-氯丁烷-2-酮或叔丁基卤化物作为卤化氢的供体，可以在没有腐蚀性试剂（例如卤化氢或酰基氯）的情况下进行这种转化，从而大大提高了官能团耐受性和安全性。这些反应与最先进的反应相比。该方法可以制备含有酸敏感基团的烯基卤化合物，例如叔醇、甲硅烷基醚和缩醛。这些方法的合成价值已通过实现低催化剂负载的克级合成得到证明。
• General and Selective Synthesis of (<i>Z</i>)-3-Haloacrylates via Palladium-Catalyzed Carbonylation of Terminal Alkynes
  作者：Jin-Heng Li、Shi Tang、Ye-Xiang Xie

  DOI：10.1021/jo048358r

  日期：2005.1.1

  A general and selective palladium-catalyzed carbonylation of terminal alkynes method for the synthesis of (Z)-3-haloacrylates is presented. In the presence of a catalytic amount of PdX2 and 5 equiv of CuX2 (X = Cl and Br), terminal alkynes were carbonylated to afford the corresponding (Z)-3-haloacrylates exclusively in moderate to good yields. The results showed that the effect of solvent had a fundamental

  提出了一种通用的，选择性的钯催化的末端炔烃羰基化方法，用于合成（Z）-3-卤代丙烯酸酯。在催化量的PdX 2和5当量的CuX 2（X = Cl和Br）的存在下，末端炔烃被羰基化，仅以中等到良好的产率得到相应的（Z）-3-卤代丙烯酸酯。结果表明，溶剂的影响对钯催化的羰基化反应的化学选择性和立体选择性具有根本性的影响。
• Novel Stereospecific Synthesis of 3-Chloroacrylate Esters via Palladium-Catalyzed Carbonylation of Terminal Acetylenes
  作者：Jinheng Li、Huanfeng Jiang、Aiqun Feng、Lanqi Jia

  DOI：10.1021/jo982345u

  日期：1999.8.1

  A simple and effective method for the highly regio- and stereospecific synthesis of (Z)-3-chloroacrylate esters is described. Using terminal acetylenes and primary, secondary, and tertiary aliphatic alcohols as substrates, the carbonylation reactions were carried out under carbon monoxide (1 atm) at room temperature in the presence of a catalytic amount of PdCl2 and 3 equiv of cupric chloride. Isolated yields of (Z)-3-chloroacrylate esters ranging 6 om 30% to 72% were obtained. Our results show that the polarity of the alcohol-benzene solvent plays an important role in the stereochemistry of the products.