(E)-1-cyclohexyl-2-(phenylthio)-1-hexene

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (E)-1-cyclohexyl-2-(phenylthio)-1-hexene
• 英文别名: [(E)-1-cyclohexylhex-1-en-2-yl]sulfanylbenzene
• 化学式: C₁₈H₂₆S
• 分子量: 274.47
• InChiKey: PELJTBHDFRXIRW-OBGWFSINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (E)-1-cyclohexyl-1-(dicyclohexylboryl)-2-(phenylthio)-1-hexene 在 甲醇 、 LiCu 、 甲基锂 作用下， 以55%的产率得到(E)-1-cyclohexyl-2-(phenylthio)-1-hexene
  参考文献：
  名称：

  Vinylborane and vinylchalcogenide mediated synthesis of tri- and tetrasubstituted olefins from 1-alkynes

  摘要：

  The title olefins have been prepared with high regio- and stereocontrol from I-alkynes through vinyl boranes / vinyl chalcogenides; the reaction sequences involved protonolysis or transmetallation - alkylation of the boranes followed by an Ni(0) catalyzed coupling reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01938-8

文献信息

• Chalcogen electrophile induced rearrangement of 1-alkynyltrialkyl borates: controlled syntheses of trisubstituted olefins from 1-alkynes
  作者：Julien Gerard、László Hevesi

  DOI：10.1016/s0040-4020(01)00904-8

  日期：2001.10

  The reaction of 1-alkynyltrialkyl borates with sulfenyl, selenenyl and tellurenyl halides produces β-chalcogeno alkenylboranes in good yields, with a cis relationship between the boron and the chalcogen moities. Protodeborylation of these compounds by acetic acid, or by a transmetalation–protonolysis sequence, leads to vinyl chalcogenides, which can be converted to alkenes by means of a nickel catalyzed

  1-炔基三烷基硼酸酯与亚硫基，亚硒基和碲基卤化物的反应以良好的产率产生β-硫属元素烯基硼烷，其中硼与硫属元素之间具有顺式关系。这些化合物通过乙酸或通过金属转移-质子分解序列进行原脱硼化反应，生成乙烯基硫属元素化物，可以通过镍与格利雅试剂的偶联将其转化为烯烃。由于最后两个步骤是在保留立体化学的情况下发生的，因此整个序列代表了高度区域和立体选择性的烯烃合成。
• Transformation of β-chalcogeno alkenylboranes into tetrasubstituted olefins
  作者：Julien Gerard、László Hevesi

  DOI：10.1016/j.tet.2003.11.023

  日期：2004.1

  In view of generating trisubstituted vinylic chalcogen derivatives, β-chalcogeno alkenylboranes generated through the chalcogen electrophile induced rearrangements of 1-alkynyltrialkyl borates have been subjected to Suzuki–Miyaura coupling and to boron to copper transmetalation followed by alkylation. Some of the trisubstituted vinyl sulfides obtained by this latter strategy have been converted efficiently

  考虑到生成三取代乙烯基硫属元素衍生物，通过硫族元素亲电试剂诱导的1-炔基三烷基硼酸酯重排生成的β-硫属元素烯基硼烷已经进行了Suzuki-Miyaura偶联，并进行了硼到铜的重金属化反应，然后进行了烷基化反应。通过后一种策略获得的一些三取代的乙烯基硫化物已通过NiCl 2（dmpe）催化与各种格氏试剂的偶联有效地转化为标题烯烃。
• Vinylborane and vinylchalcogenide mediated synthesis of tri- and tetrasubstituted olefins from 1-alkynes
  作者：Julien Gerard、Emerance Bietlot、Làszlò Hevesi

  DOI：10.1016/s0040-4039(98)01938-8

  日期：1998.11

  The title olefins have been prepared with high regio- and stereocontrol from I-alkynes through vinyl boranes / vinyl chalcogenides; the reaction sequences involved protonolysis or transmetallation - alkylation of the boranes followed by an Ni(0) catalyzed coupling reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.