2-(phenylsulfonyl)-2-propenyl-N-p-chloroaniline | 142231-45-6

• 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: 2-(phenylsulfonyl)-2-propenyl-N-p-chloroaniline
• 英文别名: N-[2-(benzenesulfonyl)prop-2-enyl]-4-chloroaniline
• CAS: 142231-45-6
• 化学式: C₁₅H₁₄ClNO₂S
• 分子量: 307.801
• InChiKey: USOVHBYGYDHDNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-(phenylsulfonyl)-2-propenyl alcohol 以 苯 为溶剂， 生成 2-(phenylsulfonyl)-2-propenyl-N-p-chloroaniline
  参考文献：
  名称：

  Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(tert-Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group

  摘要：

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.

  DOI：

  10.1021/jo982141d

文献信息

• Yamamoto, Iwao; Kajiwara, Kouji; Fujimoto, Tetsuya, Journal of Heterocyclic Chemistry, 1992, vol. 29, # 2, p. 515 - 518
  作者：Yamamoto, Iwao、Kajiwara, Kouji、Fujimoto, Tetsuya、Ohta, Kazutika

  DOI：——

  日期：——
• Amino-Protecting Groups Subject to Deblocking under Conditions of Nucleophilic Addition to a Michael Acceptor. Structure−Reactivity Studies and Use of the 2-(<i>tert-</i>Butylsulfonyl)-2-propenyloxycarbonyl (Bspoc) Group
  作者：Louis A. Carpino、Michael Philbin

  DOI：10.1021/jo982141d

  日期：1999.6.1

  A new type of amino-protecting group is described in which a Michael acceptor is incorporated into the protectant so that treatment with a nucleophile will trigger deblocking. Comparison of various Michael accepters showed that for several key electron-withdrawing groups, the order of reactivity was C6H5SO2 > Me3CSO2 > COOEt > CsH5SO > C(6)H(4)NO(2-)p. The reactivity of the nucleophile. (e.g., primary and secondary aliphatic amines) followed an order related to both intrinsic basicity and steric effects. beta-Substituents in the Michael acceptor caused significant retardation of the deblocking process. The Bspoc function was chosen for initial elaboration into a practical system for use in peptide synthesis. Bspoc amino acid chlorides were used as coupling agents and silica-tethered secondary amines as deblocking agents. With the latter, deblocking occurs cleanly and no byproducts remain in the organic solvent in which the deblocking is executed.