<2,2-bis(phenylthio)ethyl>oxirane | 112185-47-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: <2,2-bis(phenylthio)ethyl>oxirane
• 英文别名: 2-[2,2-Bis(phenylsulfanyl)ethyl]oxirane
• CAS: 112185-47-4
• 化学式: C₁₆H₁₆OS₂
• 分子量: 288.434
• InChiKey: PNZAXASWXASUJH-UHFFFAOYSA-N

物化性质

• 沸点：
  436.2±15.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  <2,2-bis(phenylthio)ethyl>oxirane 在 间氯过氧苯甲酸 作用下， 生成 2-[2,2-双(苯磺酰基)乙基]环氧乙烷
  参考文献：
  名称：

  ω-环氧1,1-双砜的碱催化环化反应。反应性和选择性与环大小的关系

  摘要：

  末端环氧双砜的环化可以两种不同的方式发生。三元至七元环的闭环速率跨越三个数量级。

  DOI：

  10.1039/c39870000406
• 作为产物：
  描述：

  双(苯硫基)甲烷 、 环氧溴丙烷 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以87%的产率得到<2,2-bis(phenylthio)ethyl>oxirane
  参考文献：
  名称：

  Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones

  摘要：

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.

  DOI：

  10.1021/jo00011a017

文献信息

• A versatile vinyl sulphide synthesis using benzenesulphenyl chloride
  作者：Birgit Bartels、Roger Hunter、Clive D. Simon、Geoffrey D. Tomlinson

  DOI：10.1016/s0040-4039(00)96263-4

  日期：——

  Benzenesulphenyl chloride (PhSCl) in CH2Cl2 at −78°C converts thioacetals and thioketals to their α-chlorosulphides which afford vinyl sulphides on elimination. The method is compatible with a range of functionality.

  在-78°C下于CH 2 Cl 2中的苯磺酰氯（PhSCl）将硫缩醛和硫缩酮转化为它们的α-氯硫化物，从而在消除时提供乙烯基硫化物。该方法与一系列功能兼容。
• BENEDETTI, FABIO;BERTI, FEDERICO;FABRISSIN, SILVIO;GIANFERRARA, TERESA;RI+, J. ORG. CHEM., 56,(1991) N1, C. 3530-3537
  作者：BENEDETTI, FABIO、BERTI, FEDERICO、FABRISSIN, SILVIO、GIANFERRARA, TERESA、RI+

  DOI：——

  日期：——
• BENEDETTI F.; FABRISSIN S.; GIANFERRARA T.; RISALITI A., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 6, 406-407
  作者：BENEDETTI F.、 FABRISSIN S.、 GIANFERRARA T.、 RISALITI A.

  DOI：——

  日期：——
• BARTELS, BIRGIT;HUNTER, ROGER;SIMON, CLIVE D.;TOMLINSON, GEOFFREY D., TETRAHEDRON LETT., 28,(1987) N 26, 2985-2988
  作者：BARTELS, BIRGIT、HUNTER, ROGER、SIMON, CLIVE D.、TOMLINSON, GEOFFREY D.

  DOI：——

  日期：——
• Methyl effects in the cyclization of .gamma.-epoxy bis-sulfones
  作者：Fabio Benedetti、Federico Berti、Silvio Fabrissin、Teresa Gianferrara、Amerigo Risaliti

  DOI：10.1021/jo00011a017

  日期：1991.5

  A quantitative study on the effects of methyl and gem-dimethyl groups in the intramolecular ring opening of epoxides by bis-sulfonyl carbanions is reported for the formation of cyclopropanes. Reaction rates are increased by methyl groups on the chain connecting the nucleophile with the oxirane and depressed by methyl substitution in the epoxide ring. When gem-dimethyl groups are present on the epoxide, ring opening is apparently inhibited. It will be shown that in this case the reaction is reversible and the apparent stabilization of the gem-dimethyl-substituted oxirane is actually due to a combination of effects on both the forward and the reverse reactions. On the basis of current theories on intramolecular reactions, it is suggested that release of ground-state strain and van der Waals repulsions in the transition state can account for the observed reactivity.