2-[2,2-双(苯磺酰基)乙基]环氧乙烷 | 112185-38-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[2,2-双(苯磺酰基)乙基]环氧乙烷
• 英文名称: <2,2-bis(phenylsulfonyl)ethyl>oxirane
• 英文别名: 2-[2,2-Di(benzenesulfonyl)ethyl]oxirane；2-[2,2-bis(benzenesulfonyl)ethyl]oxirane
• CAS: 112185-38-3
• 化学式: C₁₆H₁₆O₅S₂
• 分子量: 352.432
• InChiKey: MEBGRLUGHVYISI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 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：
  97.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[2,2-双(苯磺酰基)乙基]环氧乙烷 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以97%的产率得到2,2-bis(phenylsulfonyl)cyclopropanemethanol
  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 在 间氯过氧苯甲酸 、 环氧溴丙烷 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

文献信息

• Gold-Catalysed Activation of Epoxides: Application in the Synthesis of Bicyclic Ketals
  作者：Rengarajan Balamurugan、Raveendra Babu Kothapalli、Ganesh Kumar Thota

  DOI：10.1002/ejoc.201001214

  日期：2011.3

  Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with C≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation

  介绍了金催化从环氧化物生成二醇等价物及其与 C≡C 键的分子内反应生成双环缩酮。该反应主要涉及丙酮化物的形成，其随后在金催化条件下分子内在炔烃上环化。这种方法可以扩展到制造光学纯的双环缩酮。进行氘掺入实验以确定反应机理。
• 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.
• Intramolecular Ring Opening of Epoxides by Bis-Activated Carbanions. The Influence of Ring Size on Reactivity and Selectivity
  作者：Fabio Benedetti、Federico Berti、Silvio Fabrissin、Teresa Gianferrara

  DOI：10.1021/jo00085a045

  日期：1994.3

  A quantitative study on the effect of ring size in the intramolecular ring opening of epoxides by carbanions is described. Two series of substrates were examined: alpha,alpha-bis-sulfonyl omega-epoxides 1 and alpha-cyano-alpha-sulfonyl omega-epoxides 2; in each series the carbanion is tethered to the epoxide by a chain of variable length from one to four methylene groups. The nucleophile can attack either electrophilic position of the oxirane ring, or both; exo ring opening of cyano sulfonyl epoxides 2 is followed by a second cyclization leading eventually to bicyclic, fused gamma-lactones. Both series of epoxides show the same trend of reactivity as a function of ring size, in the formation of three- to seven-membered rings, with reactivity maxima corresponding to the formation of cyclopropane and cyclopentane derivatives. Unlike S(N)2 ring closure of omega-halogeno carbanions, cyclization to a five-membered ring is the fastest process in this case. The ratio k3/k5 between formation of three- and five-membered rings drops from over 100, in the S(N)2 cyclization of omega-iodo bis-sulfones, to less than 0.5, in the cyclization of omega-epoxy bis-sulfones 1. The difference is discussed in terms of trajectory of approach of the carbanion to the nucleophilic center. Cyclization of cyano sulfonyl epoxide 2a, in which the nucleophilic center and the epoxide are spaced by a single methylene group, is diastereoselective and leads to a bicyclic product with a cis fusion between the gamma-lactone and the cyclopropane ring.
• 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：——