(R)-N-(2-nitrophenylsulfonyl)phenylglycine methyl ester | 1001599-55-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (R)-N-(2-nitrophenylsulfonyl)phenylglycine methyl ester
• 英文别名: methyl (2R)-2-[(2-nitrophenyl)sulfonylamino]-2-phenylacetate
• CAS: 1001599-55-8
• 化学式: C₁₅H₁₄N₂O₆S
• 分子量: 350.352
• InChiKey: SSRRQMBEWVHEPU-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.79
• 重原子数：
  24.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  115.61
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (R)-N-(2-nitrophenylsulfonyl)phenylglycine methyl ester 在 lithium iodide 作用下， 以 乙酸乙酯 为溶剂， 反应 6.0h， 以94%的产率得到(R)-N-(2-nitrophenylsulfonyl)phenylglycine
  参考文献：
  名称：

  Enantioselective amination of silylketene acetals with (N-arylsulfonylimino)phenyliodinanes catalyzed by chiral dirhodium(II) carboxylates: asymmetric synthesis of phenylglycine derivatives

  摘要：

  The first catalytic enantioselective amination of silylketene acetals with (N-arylsulfonylimino) phenyliodinanes is described. The reaction of silylketene acetals derived from methyl phenylacetates with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN = IPh) under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh-2(S-TCPTTL)(4), proceeds in benzene at room temperature to give N-(2-nitrophenylsulfonyl) phenylglycine derivatives in high yields and with enantioselectivities of up to 99% ee. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.087
• 作为产物：
  描述：

  、 [N-(2-nitrophenylsulfonyl)imino]phenyliodinane 在 Rh₂(N-Cl₄-phthaloyl-(S)-tert-leucinate)4*2EtOAc 作用下， 以 苯 为溶剂， 反应 3.0h， 以98%的产率得到(R)-N-(2-nitrophenylsulfonyl)phenylglycine methyl ester
  参考文献：
  名称：

  Enantioselective amination of silylketene acetals with (N-arylsulfonylimino)phenyliodinanes catalyzed by chiral dirhodium(II) carboxylates: asymmetric synthesis of phenylglycine derivatives

  摘要：

  The first catalytic enantioselective amination of silylketene acetals with (N-arylsulfonylimino) phenyliodinanes is described. The reaction of silylketene acetals derived from methyl phenylacetates with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN = IPh) under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh-2(S-TCPTTL)(4), proceeds in benzene at room temperature to give N-(2-nitrophenylsulfonyl) phenylglycine derivatives in high yields and with enantioselectivities of up to 99% ee. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.10.087

文献信息

• Enantioselective amination of silylketene acetals with (N-arylsulfonylimino)phenyliodinanes catalyzed by chiral dirhodium(II) carboxylates: asymmetric synthesis of phenylglycine derivatives
  作者：Masahiko Tanaka、Yasunobu Kurosaki、Takuya Washio、Masahiro Anada、Shunichi Hashimoto

  DOI：10.1016/j.tetlet.2007.10.087

  日期：2007.12

  The first catalytic enantioselective amination of silylketene acetals with (N-arylsulfonylimino) phenyliodinanes is described. The reaction of silylketene acetals derived from methyl phenylacetates with [N-(2-nitrophenylsulfonyl)imino] phenyliodinane (NsN = IPh) under the catalysis of dirhodium(II) tetrakis[N-tetrachlorophthaloyl-(S)-tert-leucinate], Rh-2(S-TCPTTL)(4), proceeds in benzene at room temperature to give N-(2-nitrophenylsulfonyl) phenylglycine derivatives in high yields and with enantioselectivities of up to 99% ee. (C) 2007 Elsevier Ltd. All rights reserved.