3-methylbuta-1,2-dienyl phenyl sulfide | 65108-53-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-methylbuta-1,2-dienyl phenyl sulfide
• 英文别名: 3-methyl-1-(phenylthio)-1,2-butadiene；3-methyl-1-phenylthiobuta-1,2-diene；Phenylthioallene；3-Methyl-1-phenylthio-butadien-1,2；3-Thiomethoxy-3,3-dimethyl-allen；Benzene, [(3-methyl-1,2-butadienyl)thio]-
• CAS: 65108-53-4
• 化学式: C₁₁H₁₂S
• 分子量: 176.282
• InChiKey: OFSFBXPMVYMWEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  3-methylbuta-1,2-dienyl phenyl sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 生成 (E)-3-methyl-1-(phenylsulfinyl)buta-1,3-diene
  参考文献：
  名称：

  Guittet, Eric; Julia, Sylvestre, Synthetic Communications, 1981, vol. 11, # 9, p. 697 - 708

  摘要：

  DOI：
• 作为产物：
  描述：

  {[1-(Benzenesulfinyl)-3-methylbuta-1,2-dien-1-yl]sulfanyl}benzene 在 甲基锂 作用下， 以 乙醚 为溶剂， 以56%的产率得到3-methylbuta-1,2-dienyl phenyl sulfide
  参考文献：
  名称：

  亚丙基亚砜的化学：炔醇的新转化

  摘要：

  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。

  DOI：

  10.1039/c39830001209

文献信息

• Contrasting reactivity in Lewis acid-promoted reactions of thio- and silyl-allenes with 1,4-benzoquinones
  作者：Thomas A. Engler、Konstantinos Agrios、Jayachandra P. Reddy、Rajesh Iyengar

  DOI：10.1016/0040-4039(95)02164-7

  日期：1996.1

  In Ti(IV)-promoted reactions with 2-methoxy-1,4-benzoquinones 3, thioallenes 1 give 2+2 and/or 3+2 products via attack on a CC moiety of the quinone, whereas silylallene 2 gives products derived from attack on a carbonyl group of the quinone.

  在Ti（IV）促进的与2-甲氧基-1,4-苯醌3的反应中，硫代烯1通过攻击醌的CC部分产生2 + 2和/或3 + 2产物，而甲硅烷基2产生产物由攻击醌的羰基衍生而来。
• 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：——