6,6-bis(phenylsulfonyl)-1-hexene | 112185-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6,6-bis(phenylsulfonyl)-1-hexene
• 英文别名: dimethyl 2-(pent-4-en-1-yl)malonate；1-(benzenesulfonyl)hex-5-enylsulfonylbenzene
• CAS: 112185-49-6
• 化学式: C₁₈H₂₀O₄S₂
• 分子量: 364.486
• InChiKey: KQUGZFCIANQBFX-UHFFFAOYSA-N

物化性质

• 沸点：
  601.2±55.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  68.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  6,6-bis(phenylsulfonyl)-1-hexene 在 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 3,3-bis(phenylsulphonyl)cyclohexanol
  参考文献：
  名称：

  Intramolecular Ring Opening of Epoxides by Bis-Activated Carbanions. The Influence of Ring Size on Reactivity and Selectivity

  摘要：

  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.

  DOI：

  10.1021/jo00085a045
• 作为产物：
  描述：

  双(苯硫基)甲烷 在 sodium hydride 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6,6-bis(phenylsulfonyl)-1-hexene
  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

• Enantioselective Construction of Functionalized Cyclopentanes by a Relay Ring-Closing Metathesis and Chiral Amine (Thio)urea-Promoted Michael Addition
  作者：Wei Wang、Yinan Zhang、Xixi Song、Xiaobei Chen、Aiguo Song、Shilei Zhang

  DOI：10.1055/s-0034-1378321

  日期：——

  that permits ring-closing metathesis and bifunctional chiral amine (thio)urea-catalyzed Michael­ addition reactions to proceed in a one-pot fashion. The process offers an alternative approach to the synthesis of structurally diverse chiral cyclopentanes in good yields and good enantioselectivities. A relay strategy is described that permits ring-closing metathesis and bifunctional chiral amine (thio)urea-catalyzed

  摘要 描述了一种中继策略，该策略允许闭环复分解和双功能手性胺（硫）脲催化的迈克尔加成反应以一锅法进行。该方法提供了另一种途径，以高收率和良好对映选择性合成结构多样的手性环戊烷。 描述了一种中继策略，该策略允许闭环复分解和双功能手性胺（硫）脲催化的迈克尔加成反应以一锅法进行。该方法提供了另一种途径，以高收率和良好对映选择性合成结构多样的手性环戊烷。
• SmI2 mediated reductive addition of bis-phenylsulfones to ketones
  作者：S. Chandrasekhar、Jurong Yu、J.R. Falck、C. Mioskowski

  DOI：10.1016/s0040-4039(00)73520-9

  日期：1994.7

  SmI2 mediates the in situ reductive addition of geminal bis-phenylsulfones to unhindered ketones at room temperature affording beta-hydroxyphenylsulfones in good to excellent yields.
• Benedetti Fabio, Berti Federico, Fabrisain Silvio, Gianferrara Teresa, J. Org. Chem, 59 (1994) N 6, S 1518-1524
  作者：Benedetti Fabio, Berti Federico, Fabrisain Silvio, Gianferrara Teresa

  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：——