N-2-(p-chlorophenyl)ethyl-N-p-nitrophenyl-α-methoxycarbonyl-α-diazoacetamide | 201347-16-2

• 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: N-2-(p-chlorophenyl)ethyl-N-p-nitrophenyl-α-methoxycarbonyl-α-diazoacetamide
• 英文别名: methyl 3-[N-[2-(4-chlorophenyl)ethyl]-4-nitroanilino]-2-diazo-3-oxopropanoate
• CAS: 201347-16-2
• 化学式: C₁₈H₁₅ClN₄O₅
• 分子量: 402.794
• InChiKey: JVPHRAIPFKIYMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  94.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-2-(p-chlorophenyl)ethyl-N-p-nitrophenyl-α-methoxycarbonyl-α-diazoacetamide 在 dirhodium(II) tetrakis[(S)-N-phthaloyl-tert-leucinate] 盐酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 R(+)-巴氯芬盐酸盐
  参考文献：
  名称：

  Enantioselective Synthesis of 4-Substituted 2-Pyrrolidinones by Site-selective C-H Insertion of α-Methoxycarbonyl-α-diazoacetanilides Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]

  摘要：

  Site- and enantioselective intramolecular C-H insertion of alpha-methoxycarbonyl-alpha-diazoacetamides has been achieved by exploiting a p-nitrophenyl group as the N-substituent and dirhodium(ll) tetrakis[N-phthaloyl-(S)-tert-leucinate] as catalyst, leading to the formation of 4-substituted 2-pyrrolidinone derivatives of up to 82% ee. The efficiency of the present protocol has been verified well by a short-step synthesis of(R)-(-)-baclofen. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10493-2
• 作为产物：
  描述：

  对氟硝基苯 在 4-乙酰氨基苯磺酰叠氮 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 23.0h， 生成 N-2-(p-chlorophenyl)ethyl-N-p-nitrophenyl-α-methoxycarbonyl-α-diazoacetamide
  参考文献：
  名称：

  Enantioselective Synthesis of 4-Substituted 2-Pyrrolidinones by Site-selective C-H Insertion of α-Methoxycarbonyl-α-diazoacetanilides Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]

  摘要：

  Site- and enantioselective intramolecular C-H insertion of alpha-methoxycarbonyl-alpha-diazoacetamides has been achieved by exploiting a p-nitrophenyl group as the N-substituent and dirhodium(ll) tetrakis[N-phthaloyl-(S)-tert-leucinate] as catalyst, leading to the formation of 4-substituted 2-pyrrolidinone derivatives of up to 82% ee. The efficiency of the present protocol has been verified well by a short-step synthesis of(R)-(-)-baclofen. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10493-2

文献信息

• Enantioselective Synthesis of 4-Substituted 2-Pyrrolidinones by Site-selective C-H Insertion of α-Methoxycarbonyl-α-diazoacetanilides Catalyzed by Dirhodium(II) Tetrakis[N-phthaloyl-(S)-tert-leucinate]
  作者：Masahiro Anada、Shun-ichi Hashimoto

  DOI：10.1016/s0040-4039(97)10493-2

  日期：1998.1

  Site- and enantioselective intramolecular C-H insertion of alpha-methoxycarbonyl-alpha-diazoacetamides has been achieved by exploiting a p-nitrophenyl group as the N-substituent and dirhodium(ll) tetrakis[N-phthaloyl-(S)-tert-leucinate] as catalyst, leading to the formation of 4-substituted 2-pyrrolidinone derivatives of up to 82% ee. The efficiency of the present protocol has been verified well by a short-step synthesis of(R)-(-)-baclofen. (C) 1997 Elsevier Science Ltd. All rights reserved.