1-iodo-3-methylbut-1-ene

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 1-iodo-3-methylbut-1-ene
• 英文别名: 1-Iodo-3-methylbutene
• 化学式: C₅H₉I
• 分子量: 196.031
• InChiKey: SESUMRHCXRFUHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  苯乙炔 、 1-iodo-3-methylbut-1-ene 在 copper(l) iodide 、 potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 以73%的产率得到1-Phenyl-5-methyl-hex-1-yn-3-ene
  参考文献：
  名称：

  Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes

  摘要：

  The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPhs in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields. Addition of PPh3 is essential for the reaction to proceed catalytically. Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations. While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes. A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.

  DOI：

  10.1021/jo00069a040
• 作为产物：
  描述：

  3-甲基-1-丁炔 在 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) 、 二异丁基氢化铝 、 N-碘代丁二酰亚胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 19.0h， 生成 2-iodo-3-methylbut-1-ene 、 1-iodo-3-methylbut-1-ene
  参考文献：
  名称：

  挑战香根草的分子参数：结构，气味中的4,5-二甲基-3-（3'-甲基丁-1'-en-2'-基）-4-苯基环戊-2-2-恩一酮？

  摘要：

  不幸的是没有！–虽然在经典的Stork–Danheiser路线上合成终于成功，但简化的目标结构（旨在由伦敦分散部队限制以模拟齐氮烯酮）仅具有微弱的木质气味，而没有典型的香根草特征。因此，最终香根草铅结构的问题以及易于获得的合成香根草气味的争夺仍然悬而未决。

  DOI：

  10.1002/ejoc.201900163

文献信息

• Challenging the Molecular Parameters of Vetiver: Can 4,5-Dimethyl-3-(3′-methylbut-1′-en-2′-yl)-4-phenylcyclopent-2-en-1-one Mimic Zizaenones in Structure and Odor?
  作者：Patrick Pfaff、Halima Mouhib、Philip Kraft

  DOI：10.1002/ejoc.201900163

  日期：2019.4.24

  successful on a classical Stork–Danheiser route, the simplified target structure, designed to be confined by London dispersion forces to mimic zizaenones, only possesses a weak woody odor but no typical vetiver character. So, the question of the ultimate vetiver lead structure and the race for an easily accessible synthetic vetiver odorant remain open.

  不幸的是没有！–虽然在经典的Stork–Danheiser路线上合成终于成功，但简化的目标结构（旨在由伦敦分散部队限制以模拟齐氮烯酮）仅具有微弱的木质气味，而没有典型的香根草特征。因此，最终香根草铅结构的问题以及易于获得的合成香根草气味的争夺仍然悬而未决。
• Synthesis of aryl- and vinylacetylene derivatives by copper-catalyzed reaction of aryl and vinyl iodides with terminal alkynes
  作者：Kazumi Okuro、Makoto Furuune、Masahiro Enna、Masahiro Miura、Masakatsu Nomura

  DOI：10.1021/jo00069a040

  日期：1993.8

  The coupling reaction of aryl iodides with terminal alkynes by using a catalyst system of CuI-PPhs in the presence of K2CO3 as base gives the corresponding arylated alkynes in excellent yields. Addition of PPh3 is essential for the reaction to proceed catalytically. Vinyl iodides also react smoothly with the alkynes to give enyne compounds with retention of the configurations. While DMF and DMSO can be used as solvents, DMSO is found to be effective for the reaction with aliphatic terminal alkynes. A reaction mechanism involving initial formation of copper acetylide species coordinated by PPh3 followed by reaction of aryl and vinyl iodides is proposed.