1,2-环硫-5-己烯 | 6766-70-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硫杂环丙烷
• 中文名称: 1,2-环硫-5-己烯
• 英文名称: 1,2-epithio-5-hexene
• 英文别名: but-3-enyl-thiirane；2-(3-Butenyl)thiirane；2-but-3-enylthiirane
• CAS: 6766-70-7
• 化学式: C₆H₁₀S
• 分子量: 114.211
• InChiKey: TZUVROWYCLDYJK-UHFFFAOYSA-N

物化性质

• 沸点：
  42-43.5 °C(Press: 10 Torr)
• 密度：
  0.964±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  1,2-环硫-5-己烯 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1,5-已二烯
  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-环氧基-5-己烯 在 硫脲 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以32%的产率得到1,2-环硫-5-己烯
  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。
• Bis(trimethylsilyl)selenide in the Selective Synthesis of β-Hydroxy, β-Mercapto, and β-Amino Diorganyl Diselenides and Selenides Through Ring Opening of Strained Heterocycles
  作者：Damiano Tanini、Alessandro Degl'Innocenti、Antonella Capperucci

  DOI：10.1002/ejoc.201403015

  日期：2015.1

  dialkyl diselenides and selenides is described through reaction of bis(trimethylsilyl)selenide with epoxides, thiiranes, and aziridines catalyzed by tetrabutylammonium fluoride. Selective formation of a wide variety of β-hydroxy, β-mercapto, and β-amino diselenides and selenides is achieved by controlling the reaction conditions in the regioselective attack of the silyl selenide onto the ring-strained

  通过双（三甲基甲硅烷基）硒化物与环氧化物、硫杂环丙烷和氮丙啶在四丁基氟化铵催化下的反应，描述了一种合成 β-取代的二烷基二硒化物和硒化物的新方法。选择性形成多种 β-羟基、β-巯基和 β-氨基二硒化物和硒化物是通过控制硒化甲硅烷对环应变杂环的区域选择性攻击的反应条件来实现的。所有反应都以高度区域选择性和对映体保守的方式发生，以良好到高产率提供标题化合物。测量硒 77 NMR 化学位移以验证 β 取代的二硒化物和硒化物的选择性形成。
• Theoretical and Experimental Analyses of the Deprotonation of Thiirane S-Oxides: The Stereoselective Formation of trans-Alkyl- and gem-Silylethenesulfenate Anions
  作者：Mitchell D. Refvik、Robert D. J. Froese、John D. Goddard、Hung H. Pham、Mark F. Pippert、Adrian L. Schwan

  DOI：10.1021/ja00106a022

  日期：1995.1

  Experimental and theoretical studies of the regioselective deprotonation of thiirane S-oxides are reported. Experimentally under the reaction conditions of LiHMDS/THF/-78 degrees C with anti-alkylthiirane S-oxides or anti-silylthiirane S-oxides as starting materials, the products of ring-opening are (E)-2-alkylethenesulfenate and 1-silylethenesulfenate anions, respectively. Experiments involving deuterium labeling clearly indicate that a regioselective deprotonation reaction was followed by a stereoselective ring-opening. Ab initio methods at both the Hartree-Fock and Moller-Plesset perturbation theory levels with the 6-31+G(d) basis set were used to examine both lithiated methyl- and silylthiirane S-oxides. Of the possible anti-substituted species, the coordination of the lithium anti to the methyl and gem to the silyl is predicted to be the most stable. These stable intermediates with the lithium syn to the sulfoxide could ring-open to yield the experimentally observed products.
• CROZET, M. P.;KAAFARANI, M.;KASSAR, W.;SURZUR, J. -M., TETRAHEDRON LETT., 1982, 23, N 48, 5039-5042
  作者：CROZET, M. P.、KAAFARANI, M.、KASSAR, W.、SURZUR, J. -M.

  DOI：——

  日期：——
• COMPOSITION AND POLYMER
  申请人：Asahi Kasei Kabushiki Kaisha

  公开号：EP2735581B1

  公开（公告）日：2021-07-14