5,5-bis(phenylsulfonyl)-1-pentene | 112185-48-5

• 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: 5,5-bis(phenylsulfonyl)-1-pentene
• 英文别名: 1-(benzenesulfonyl)pent-4-enylsulfonylbenzene
• CAS: 112185-48-5
• 化学式: C₁₇H₁₈O₄S₂
• 分子量: 350.46
• InChiKey: WFOOHXGEVQEVIH-UHFFFAOYSA-N

物化性质

• 沸点：
  571.3±50.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  5,5-bis(phenylsulfonyl)-1-pentene 在 间氯过氧苯甲酸 作用下， 生成 <3,3-bis(phenylsulfonyl)propyl>oxirane
  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 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 5,5-bis(phenylsulfonyl)-1-pentene
  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

• Rhodium(I)-Catalyzed ‘Metallo-Ene’ Cyclizations/β-Eliminations
  作者：Wolfgang Oppolzer、Alois Fürstner

  DOI：10.1002/hlca.19930760618

  日期：1993.9.22

  Octadienyl carbonates 5 provide cyclic 1,4-dienes 6 when treated with Rh1 complexes (1–10 mol-%) at 80°. Similar cyclization of cyclohexenyl acetate 8 affords cis- fused hexahydroindene 9. Analogous ring closures of nonadienyl carbonate 10 yield preferably the cis-divinypyrrolidine 11 with Rh1 catalysis but the trans-isomer 12 when catalyzed by Pd0. Azaoctadienyl carbonate 5a undergoes elimination

  当在80°下用Rh 1配合物（1-10 mol％）处理时，碳酸辛二烯酯5可提供环状1,4-二烯6。环己烯基乙酸酯8的类似环化反应可得到顺式稠合六氢茚9。碳酸壬二烯基酯10的类似的闭环优选在Rh 1催化下产生顺式-二乙烯基吡咯烷11，而在Pd 0催化下则形成反式异构体12。碳酸氮杂二烯基酯5a被[RhH（PPh 3）4消除]（5 mol％，80°）在MeCN中得到无环三烯。7。
• Bis(phenylsulfonyl)methane mediated synthesis of olefins <i>via</i> a halogen elimination and double bond migration
  作者：Jing Jiang、Ying Hu、Xin Cai、Liudi Wang、Yanwei Hu、Shaohua Chen、Shilei Zhang、Yinan Zhang

  DOI：10.1039/c8ob00033f

  日期：——

  An effective dehydrochlorination of bis(phenylsulfonyl)alkane to prepare alkene building blocks is developed. The elimination together with double bond migration results in a variety of β,γ-unsaturated bis(phenylsulfonyl)olefins in good yields with only E geometry. The following chemical diversification represents an easy and straightforward access to a series of alkene building blocks.

  开发了一种有效的双（苯基磺酰基）烷烃的脱氯化氢方法，以制备烯烃结构单元。消除和双键迁移导致仅具有E几何形状的各种β，γ-不饱和双（苯磺酰基）烯烃以良好的产率。以下化学多样化代表了轻松，直接地获得一系列烯烃构造单元的途径。
• Pd-catalyzed borylative cyclisation of 1,7-enynes
  作者：Virtudes Pardo-Rodríguez、Elena Buñuel、Daniel Collado-Sanz、Diego J. Cárdenas

  DOI：10.1039/c2cc34468h

  日期：——

  Reaction of a variety of 1,7-enynes with bis(pinacolato) diboron catalysed by Pd bis(trifluoroacetate) affords homoallylic and allylic boronates containing a six membered carbo- or heterocycle, by formation of C–C and C–B bonds

  多种1,7-炔烃与双（匹那可酯）二硼的反应在Pd双（三氟乙酸盐）的催化下，产生含有六个成员的碳环或杂环的同 allyl 和 allyl 硼酸盐，通过形成C–C和C–B键。
• (Phenylsulfonyl)allenes as Substrates for Cycloaddition Reactions: Intramolecular Cyclizations onto Unactivated Alkenes
  作者：Albert Padwa、Michael Meske、S. Shaun Murphree、Scott H. Watterson、Zhijie Ni

  DOI：10.1021/ja00132a005

  日期：1995.7

  The reaction of a series of allyl-substituted bis(phenylsulfonyl)methanes or dimethyl malonates with 2,3-bis(phenylsulfonyl)-1,3-butadiene in the presence of base afforded alkenyl-substituted allenes in good yield. The reaction proceeds by initial attack of the soft carbanion onto the terminal position of the diene, and this is followed by PhSO(2)(-) elimination to give the phenylsulfonyl-substituted allene. Themal [2 + 2]-cycloaddition proceeded across the C-1-C-2 double bond of the allene with completely sterospecificity. Stepwise bonding prefers to occur in a 1,6-exo manner rather than in a 1,7-endo fashion. Substitution at the 7-position of the pi-bond causes a crossover in the regioselectivity of the [2 + 2]-cycloaddition process. All products can be rationalized by a mechanism which includes an initial carbon-carbon bond formation involving the central allene carbon to give a diradical intermediate. The product distribution is then determined by the substitution pattern of the alkene and the fate of the diradical intermediate.
• 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.