2-(cyclohexylidenyl)ethenyl phenyl sulfide | 69358-71-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(cyclohexylidenyl)ethenyl phenyl sulfide
• 英文别名: (1-phenylthio)-3,3-(pentamethylene)allene；2-cyclohexylidenevinyl phenyl sulfide；Benzene, [(cyclohexylideneethenyl)thio]-
• CAS: 69358-71-0
• 化学式: C₁₄H₁₆S
• 分子量: 216.347
• InChiKey: GQGCOWOIRCEVKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(cyclohexylidenyl)ethenyl phenyl sulfide 在 水 、 溴 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以63%的产率得到(Z)-1-(1'-cyclohexenyl)-1-bromo-2-(phenylsulfanyl)ethene
  参考文献：
  名称：

  Studies on the Regio- and Stereoselectivity of Halohydroxylation of 1,2-Allenyl Sulfides or Selenides

  摘要：

  It was observed that the halohydroxylation of 1,2-allenyl sulfides or selenides with Br-2 (CuBr2 or NBS) or I-2 and water demonstrated a fairly good regioselectivity (i.e., the C=C bond that is remote from the S or Se atom was halohydroxylated with the halogen atom connecting to the middle carbon atom and the hydroxyl group connecting to the non-S terminal carbon or Se-substituted terminal carbon atom of the allene moiety), leading to the synthesis of synthetically important 3-organosulfur or seleno-2-haloallylic alcohols. The stereoselectivity depends on the nature of X+ and S or Se, showing a Z-selectivity with the matched Lewis acid-base pair.

  DOI：

  10.1021/jo049593c
• 作为产物：
  描述：

  炔环己醇 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 双(2-二苯基磷苯基)醚 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.1h， 生成 2-(cyclohexylidenyl)ethenyl phenyl sulfide
  参考文献：
  名称：

  通过串联钯催化的取代和环异构化合成多取代的烯，呋喃和吡咯

  摘要：

  研究了炔丙基乙酸酯与有机硫醇铟的钯催化炔丙基取代反应，用于合成多取代的烯丙基硫化物。该程序可用于在一锅中通过串联钯催化的炔丙基取代和环异构化反应来合成多取代的呋喃和吡咯。

  DOI：

  10.1021/acs.orglett.6b03561

文献信息

• Chemistry of allene sulphoxides: novel transformations of acetylenic alcohols
  作者：Ian Cutting、Philip J. Parsons

  DOI：10.1039/c39830001209

  日期：——

  The preparation and reactions of allenes derived from 1-phenylthio substituted acetylenic alcohols are described; this chemistry offers new routes to allenyl sulphides, acyl anion equivalents, and substituted unsaturated aldehydes.

  描述了由1-苯硫基取代的炔醇衍生的丙二烯的制备和反应。这种化学方法提供了新的路线，以开发出烯丙基硫醚，酰基阴离子当量和取代的不饱和醛。
• Convenient synthesis of allenyl sulphides; application to the synthesis of αβ-unsaturated ketones
  作者：Richard C. Cookson、Philip J. Parsons

  DOI：10.1039/c39780000822

  日期：——

  P2S5 in methylene chloride containing pyridine reduces allenyl phenyl sulphoxides to sulphides; the difficult hydrolysis of the latter is eased by the introduction of a methoxy group into the benzene ring and this method then becomes a practicable synthesis of αβ-unsaturated ketones.

  含吡啶的二氯甲烷中的P 2 S 5将烯丙基苯基亚砜还原为硫化物；后者的水解难以通过引入甲氧基的成苯环缓和，则此方法变得α的切实可行合成β不饱和酮。
• Controlled carbon–sulphur or carbon–silicon bond cleavage in the reactions of alkyl-lithium reagents with a 1-silyl-1-thioallene
  作者：Alexander J. Bridges、Victor Fedji、Eugene C. Turiwski

  DOI：10.1039/c39830001093

  日期：——

  3-Methyl-1-phenylthio-1-trimethylsilylbuta-1,2-diene (3) reacts with different alkyl-lithium reagents by C–Si or C–S bond cleavage, rather than by Michael addition or metallation; one product, the α-silyl-α-lithioallene (6), is alkylated mainly γ with carbonyl compounds, but is silylated α with Et3SiCl to from the 1,1-bis-silylallene Me2CCC(SiEt3)SiMe3.

  3-甲基-1-苯硫基-1-三甲基甲硅烷基丁二烯-1,2-二烯（3）与不同的烷基锂试剂通过C-Si或C-S键断裂而不是通过迈克尔加成或金属化反应进行反应；一种产物，α-甲硅烷基-α-硫代丙二烯（6），主要是用羰基化合物对γ进行烷基化，但是用Et 3 SiCl甲硅烷基化生成1,1-双甲硅烷基亚丙Me 2 C C C（SiEt 3） SiMe 3。
• <i>o</i>-Quinone Methides from 4-Allenylcyclobutenones:  Synthesis and Chemistry
  作者：Meng Taing、Harold W. Moore

  DOI：10.1021/jo951445m

  日期：1996.1.1

  Selected 4-allenylcyclobutenones ring expand to the corresponding o-quinone methides upon thermolysis in refluxing toluene or benzene. These reactive intermediates were not isolated but trapped to give stable products. The reaction has synthetic potential as a route to highly-substituted phenols, benzofurans, and aryl analogs of hexahydrocannabinol. In addition, a unique rearrangement involving a methyl migration from silicon to carbon of selected 4-[3,3-bis(trimethylsilyl)-1,2-propadienyl]cyclobutenones to give 1,2-benzoxasilols is described. Finally, data are presented that show rapid rotation around the alkylidene bond of o-quinone methides at 30 degrees C and that 2-(1-methylethenyl)phenols are in equilibrium with the corresponding o-quinone methides.
• Phenylthiocopper trimethylphosphite complex. A reagent for the preparation of thioallenes.
  作者：Alexander J. Bridges

  DOI：10.1016/s0040-4039(00)92184-1

  日期：——