2-(phenylsulfonyl)-2-propenyl N-(p-chlorophenyl)carbamate | 134996-25-1

• 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-chlorophenyl)carbamate
• 英文别名: 2-(benzenesulfonyl)prop-2-enyl N-(4-chlorophenyl)carbamate
• CAS: 134996-25-1
• 化学式: C₁₆H₁₄ClNO₄S
• 分子量: 351.81
• InChiKey: FSPXVJNZKMDNPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(phenylsulfonyl)-2-propenyl N-(p-chlorophenyl)carbamate 以 solid 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
• 作为产物：
  描述：

  2-(phenylsulfonyl)-2-propenyl alcohol 以 四氢呋喃 、 苯 为溶剂， 生成 2-(phenylsulfonyl)-2-propenyl N-(p-chlorophenyl)carbamate
  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

• Reagents for rapid peptide synthesis
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0401817B1

  公开（公告）日：1995-09-13
• SYNTHESIS AND USE OF AMINO ACID FLUORIDES AS PEPTIDE COUPLING REAGENTS
  申请人：RESEARCH CORPORATION TECHNOLOGIES, INC.

  公开号：EP0496836A1

  公开（公告）日：1992-08-05
• EP0496836A4
  申请人：——

  公开号：EP0496836A4

  公开（公告）日：1993-05-05
• US5221754A
  申请人：——

  公开号：US5221754A

  公开（公告）日：1993-06-22
• US5510491A
  申请人：——

  公开号：US5510491A

  公开（公告）日：1996-04-23