N-(2-nitrobenzyl)-N-Aloc-L-alanine | 345207-21-8

• 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: N-(2-nitrobenzyl)-N-Aloc-L-alanine
• 英文别名: (2S)-2-[(2-nitrophenyl)methyl-prop-2-enoxycarbonylamino]propanoic acid
• CAS: 345207-21-8
• 化学式: C₁₄H₁₆N₂O₆
• 分子量: 308.291
• InChiKey: YBUPLIDXQRMBLY-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(2-nitrobenzyl)-N-Aloc-L-alanine 在 四(三苯基膦)钯 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 1.0h， 生成 (R)-3-(1H-Indol-3-yl)-2-[(S)-2-(2-nitro-benzylamino)-propionylamino]-propionic acid methyl ester
  参考文献：
  名称：

  Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G

  摘要：

  The Eguchi aza Wittig protocol has been used for the synthesis of sclerotigenin and circumdatin F by selective acylation of the more acidic anilide nitrogen of a benzodiazepinedione without the need for protecting groups. The use of the 2-nitrobenzyl group as a photochemically labile protecting group for the amide nitrogen of a diketopiperazine permits the use of the aza Wittig procedure for the synthesis of fumiquinazoline G. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00208-3
• 作为产物：
  描述：

  2-(2-nitrobenzylamino)propionic acid methyl ester 在 吡啶 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 4.0h， 生成 N-(2-nitrobenzyl)-N-Aloc-L-alanine
  参考文献：
  名称：

  Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G

  摘要：

  The Eguchi aza Wittig protocol has been used for the synthesis of sclerotigenin and circumdatin F by selective acylation of the more acidic anilide nitrogen of a benzodiazepinedione without the need for protecting groups. The use of the 2-nitrobenzyl group as a photochemically labile protecting group for the amide nitrogen of a diketopiperazine permits the use of the aza Wittig procedure for the synthesis of fumiquinazoline G. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00208-3

文献信息

• Synthesis of circumdatin F and sclerotigenin. Use of the 2-nitrobenzyl group for protection of a diketopiperazine amide; synthesis of ent -fumiquinazoline G
  作者：Barry B Snider、Marina V Busuyek

  DOI：10.1016/s0040-4020(01)00208-3

  日期：2001.4

  The Eguchi aza Wittig protocol has been used for the synthesis of sclerotigenin and circumdatin F by selective acylation of the more acidic anilide nitrogen of a benzodiazepinedione without the need for protecting groups. The use of the 2-nitrobenzyl group as a photochemically labile protecting group for the amide nitrogen of a diketopiperazine permits the use of the aza Wittig procedure for the synthesis of fumiquinazoline G. (C) 2001 Elsevier Science Ltd. All rights reserved.