2-(5-hexenyl)thiirane | 14122-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丙烷
• 英文名称: 2-(5-hexenyl)thiirane
• 英文别名: 1,2-epithio-7-octene；hex-5-enyl-thiirane；2-Hex-5-enylthiirane
• CAS: 14122-59-9
• 化学式: C₈H₁₄S
• 分子量: 142.265
• InChiKey: GPSRSFCBMVZVLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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-(5-hexenyl)thiirane 在 甲基三氧化铼(VII) 硫化氢 、 三苯基膦 作用下， 以 氘代乙腈 为溶剂， 反应 1.0h， 以100%的产率得到1,7-辛二烯
  参考文献：
  名称：

  Stereospecific rhenium catalyzed desulfurization of thiiranes

  摘要：

  甲基三氧铼催化了三苯基磷在室温下对噻吩环的高效且立体特异性的脱硫，尤其是在MTO经过硫化氢预处理后，铼的V价物种作为催化剂的活性形式。

  DOI：

  10.1039/a901708i
• 作为产物：
  描述：

  1,2-环氧-7-辛烯 在 硫脲 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以42%的产率得到2-(5-hexenyl)thiirane
  参考文献：
  名称：

  Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides

  摘要：

  The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to beta,beta'-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation. A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.

  DOI：

  10.1021/jo00125a039

文献信息

• Thiosilane- and Organoselenosilane-Mediated Novel Access to 3,7-Disubstituted-1,2,5- trithiepanes and -1,2,5-dithiaselenepanes
  作者：Antonella Capperucci、Damiano Tanini、Cosimo Borgogni、Alessandro DegľInnocenti

  DOI：10.1002/hc.21157

  日期：2014.11

  intermediate with another molecule of episulfide, followed by intramolecular oxidation of two sulfur units. When using bis(trimethylsilyl)selenide, the reaction with thiiranes and TBAF affords a smooth access to a novel class of disubstituted-1,2,5-dithiaselenepanes.

  双（三甲基甲硅烷基）硫化物在四丁基氟化铵（TBAF）催化下与不同取代的硫杂环丙烷反应，通过硫硅烷中间体与另一分子环硫化物的区域选择性反应合成 3,7-二取代-1,2,5-三硫杂环丙烷，然后是两个硫单元的分子内氧化。当使用双（三甲基甲硅烷基）硒化物时，硫杂丙烷和 TBAF 的反应可以顺利获得一类新的二取代-1,2,5-二硫杂硒烷。
• Studies on the Reaction of Thiiranes with Tributyltin Hydride
  作者：Mark H. Izraelewicz、Mohomod Nur、Richard T. Spring、Edward Turos

  DOI：10.1021/jo00107a033

  日期：1995.1
• Izraelewicz Mark H., Nur Mohamud, Spring Richard T., Turos Edward, J. Org. Chem, 60 (1995) N 2, S 470-472
  作者：Izraelewicz Mark H., Nur Mohamud, Spring Richard T., Turos Edward

  DOI：——

  日期：——
• Regiochemical and stereochemical studies on halogen-induced ring expansions of unsaturated episulfides
  作者：Xiao-Feng Ren、Monika I. Konaklieva、Edward Turos、Lynn M. Krajkowski、Charles H. Lake、Thomas S. Janik、Melvyn Rowen Churchill

  DOI：10.1021/jo00125a039

  日期：1995.10

  The reactions of unsaturated episulfides with bromine and iodine have been studied. Initially produced in the reaction is a ring opened sulfenyl halide intermediate, which in the presence of the carbon-carbon double bond or triple bond cyclizes to beta,beta'-dihalo sulfide cycloadducts. The regiochemistry and relative stereochemistry of these cyclizations have been examined as a function of the length of the tether between the episulfide moiety and the unsaturated functionality, the presence of alkyl substituents, and the type of unsaturation. A discussion of the mechanistic and stereochemical features of the ring-expansion process is presented.
• Stereospecific rhenium catalyzed desulfurization of thiiranes
  作者：Josemon Jacob、James H. Espenson

  DOI：10.1039/a901708i

  日期：——

  Methyltrioxorhenium catalyzes the efficient and stereospecific desulfurization of thiiranes by triphenylphosphine at room temperature, moreso when MTO has been pretreated with hydrogen sulfide, with a ReV species as the active form of the catalyst.

  甲基三氧铼催化了三苯基磷在室温下对噻吩环的高效且立体特异性的脱硫，尤其是在MTO经过硫化氢预处理后，铼的V价物种作为催化剂的活性形式。