4-(苯基磺酰基)-4-氰基-1-丁烯 | 125263-27-6

• 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: 4-(苯基磺酰基)-4-氰基-1-丁烯
• 英文名称: 4-(phenylsulfonyl)-4-cyano-1-butene
• 英文别名: 2-benzenesulfonyl-4-pentenonitrile；2-(Benzenesulfonyl)pent-4-enenitrile
• CAS: 125263-27-6
• 化学式: C₁₁H₁₁NO₂S
• 分子量: 221.28
• InChiKey: GZKNBEJCTYRBAF-UHFFFAOYSA-N

物化性质

• 沸点：
  416.8±45.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(苯基磺酰基)-4-氰基-1-丁烯 在 sodium ethanolate 、 间氯过氧苯甲酸 作用下， 反应 12.0h， 生成 1-Benzenesulfonyl-3-oxa-bicyclo[3.1.0]hex-2-ylideneamine
  参考文献：
  名称：

  γ，δ-环氧-α-氰基砜的环化。一种简单的非对映选择性途径，可制得环丙烷羧酸。

  摘要：

  α-氰基-α-磺酰基-γ，δ-环氧碳负离子的环化以高收率和完全非对映选择性进行，以产生环丙醇内酯，其是在顺式取代的环丙烷羧酸的合成中有用的中间体。

  DOI：

  10.1016/0040-4039(93)85066-6
• 作为产物：
  描述：

  在 chromium(VI) oxide 、 高碘酸 作用下， 以 乙酸乙酯 、 乙腈 为溶剂， 以99%的产率得到4-(苯基磺酰基)-4-氰基-1-丁烯
  参考文献：
  名称：

  在双相条件下钯催化的 α-亚磺酰基碳负离子的烯丙基烷基化

  摘要：

  钯催化的 α-亚磺酰基碳负离子的烯丙基烷基化可以在双相条件下发生。这些新条件为烯丙基化亚砜的高产率提供了一种简单、温和且有效的途径。该反应容许多种 EWG 基团作为额外的碳负离子稳定基团，例如酯、乙酰基、氰基、酰胺、磺酰基和亚磺酰基官能团。

  DOI：

  10.1055/s-2006-939702

文献信息

• Unconventional Reactivity of a Grubbs Catalyst: Hydroalkylation Overriding Metathesis
  作者：Amit Singh Adhikari、Nilanjana Majumdar

  DOI：10.1021/acs.orglett.3c03456

  日期：2023.12.8

  Unprecedented reactivity of a Grubbs catalyst has been disclosed in a reaction between vinyl azaarenes and alkenylnitriles under standard metathesis conditions. No metathesis was observed; only hydroalkylation products were obtained in high yields. The practical utility of this method has been demonstrated by the application of the products in useful transformations, e.g., the formation of cyclic iminoesters

  在标准复分解条件下，乙烯基氮杂芳烃和烯基腈之间的反应中揭示了格鲁布斯催化剂前所未有的反应活性。没有观察到复分解作用；仅以高收率获得加氢烷基化产物。该方法的实用性已通过产品在有用转化中的应用得到证明，例如环状亚氨基酯和极具挑战性的中等碳环的形成。
• Effective activation of allylic etherrs by boron oxide in palladium catalyzed allylic alkylation
  作者：Xiyan Lu、Xiaohui Jiang

  DOI：10.1016/0022-328x(89)85259-3

  日期：1989.1
• 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, 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：——
• Palladium-Catalyzed Allylic Alkylation of α-Sulfinyl Carbanions under ­Biphasic Conditions
  作者：David Madec、Giovanni Poli、Guillaume Maitro、Guillaume Prestat

  DOI：10.1055/s-2006-939702

  日期：——

  alkylation of α-sulfinyl carbanions can take place under biphasic conditions. These new conditions provide a simple, mild and efficient route to allylated sulfoxides in good yields. The reaction tolerates a wide variety of EWG groups as additional carbanion stabilizing groups such as ester, acetyl, cyano, amide, sulfonyl and sulfinyl functions.

  钯催化的 α-亚磺酰基碳负离子的烯丙基烷基化可以在双相条件下发生。这些新条件为烯丙基化亚砜的高产率提供了一种简单、温和且有效的途径。该反应容许多种 EWG 基团作为额外的碳负离子稳定基团，例如酯、乙酰基、氰基、酰胺、磺酰基和亚磺酰基官能团。