methyl (E)-6-iodo-3-methyl-2-hexenoate | 87131-46-2

• 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 (E)-6-iodo-3-methyl-2-hexenoate
• 英文别名: methyl (E)-6-iodo-3-methylhex-2-enoate
• CAS: 87131-46-2
• 化学式: C₈H₁₃IO₂
• 分子量: 268.095
• InChiKey: VUJPRRKTAFOSEQ-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 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：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-6-iodo-3-methyl-2-hexenoate 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 32.0h， 生成 (+/-)-2-methyl-2H-tetrahydrothiopheneacetic acid
  参考文献：
  名称：

  Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles

  摘要：

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.

  DOI：

  10.1021/jo00032a025
• 作为产物：
  描述：

  methyl (E)-6-hydroxy-3-methyl-2-hexenoate 在 sodium iodide 作用下， 以 吡啶 、 丙酮 为溶剂， 反应 12.0h， 生成 methyl (E)-6-iodo-3-methyl-2-hexenoate
  参考文献：
  名称：

  （E）-3、7-二甲基-2-辛烯-1、8-二酸（愈伤组织布鲁酸）的旋光形式的合成和生物活性：小豆象鼻虫交配释放信息素（erectin）的成分

  摘要：

  合成了硬木布鲁酸的两种对映体，证实了其提议的平面结构为（E）-3、7-二甲基-2-辛烯-1、8-二酸。它们都具有生物学活性，作为中华Call的交配释放信息素。

  DOI：

  10.1016/s0040-4020(01)91957-x

文献信息

• Tandem SN2-Michael reactions for the preparation of simple five- and six-membered-ring nitrogen and sulfur heterocycles
  作者：Richard A. Bunce、Christopher J. Peeples、Paul B. Jones

  DOI：10.1021/jo00032a025

  日期：1992.3

  A one-pot tandem S(N)2-Michael addition sequence has been developed for the preparation of five-membered- and six-membered-ring nitrogen and sulfur heterocycles from 6- or 7-halo-2-alkenoate esters. Nitrogen-containing rings are prepared by reaction of the omega-halo-2-alkenoate ester with a primary amine in the presence of triethylamine. The sulfur analogues are generated by thiourea displacement of the halide followed by base hydrolysis of the isothiouronium salt. Yields are routinely in the 60-80% range. Experiments are described which elucidate the chronology of the reaction sequences. Ring size and steric hindrance to the initial substitution reaction appear to be the only limitations of the procedure.
• Synthesis and biological activity of optically active forms of (E)-3, 7-dimethyl-2-octene-1, 8-dioic acid (callosobruchusic acid)
  作者：Kenji Mori、Teruhito Ito、Kaoru Tanaka、Hiroshi Honda、Izuru Yamamoto

  DOI：10.1016/s0040-4020(01)91957-x

  日期：——

  Both enantiomers of callosobruchusic acid were synthesized, confirming its proposed plane structure as (E)-3, 7-dimethyl-2-octene-1, 8-dioic acid. Both of them were biologically active as the copulation release pheromone of Callosobruchus chinensis L.

  合成了硬木布鲁酸的两种对映体，证实了其提议的平面结构为（E）-3、7-二甲基-2-辛烯-1、8-二酸。它们都具有生物学活性，作为中华Call的交配释放信息素。