(Z)-3-phenyl-2-(phenylsulfonyl)-2-propenyl chloroformate | 135204-16-9

• 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: (Z)-3-phenyl-2-(phenylsulfonyl)-2-propenyl chloroformate
• 英文别名: [(Z)-2-(benzenesulfonyl)-3-phenylprop-2-enyl] carbonochloridate
• CAS: 135204-16-9
• 化学式: C₁₆H₁₃ClO₄S
• 分子量: 336.796
• InChiKey: YNNUIIUIEFPALN-PTNGSMBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 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：
  68.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对氯苯胺 、 (Z)-3-phenyl-2-(phenylsulfonyl)-2-propenyl chloroformate 以 苯 为溶剂， 生成 (Z)-3-Phenyl-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
• 作为产物：
  描述：

  phenyl(styryl)sulfane 在 正丁基锂 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 (Z)-3-phenyl-2-(phenylsulfonyl)-2-propenyl chloroformate
  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：EP0401817A2

  公开（公告）日：1990-12-12

  This invention relates to compounds of the formula: wherein R is an electron withdrawing group; R₁ is H or COZ; X₁ and X₂ are independently H, lower alkyl, aryl, aryl lower-alkyl or polystyrene or R and X₁ taken together with the carbon atoms to which they are attached form a ring containing from 4 to 15 ring carbon atoms and may contain up to 2 heteroatoms, wherein the heteroatoms are O, S, or N; and Z is an amino acid residue, a peptide residue or a leaving group. The compounds of the present invention are adaptable as blocking or protecting groups for an amine composition useful in peptide synthesis. The present invention is also directed to a method of protecting an amino group of an organic molecule during a reaction which modifies a portion of the molecule other than the protected amino group.

  本发明涉及式中的化合物： 其中 R 是取电子基团； R₁ 是 H 或 COZ； X₁ 和 X₂ 独立地为 H、低级烷基、芳基、芳基低级烷基或聚苯乙烯，或 R 和 X₁ 与它们所连接的碳原子一起形成一个环，该环含 4 至 15 个环状碳原子，最多可包含 2 个杂原子，其中杂原子为 O、S 或 N；以及 Z 是氨基酸残基、肽残基或离去基团。本发明的化合物可用作肽合成中胺类组合物的封端或保护基团。本发明还涉及一种在反应过程中保护有机分子氨基的方法，该反应改变了分子中除受保护氨基以外的部分。
• 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