N-(2-Azidobenzoyl)-L-phenylalanine methyl ester | 142114-79-2

• 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-Azidobenzoyl)-L-phenylalanine methyl ester
• 英文别名: methyl (2S)-2-[(2-azidobenzoyl)amino]-3-phenylpropanoate
• CAS: 142114-79-2
• 化学式: C₁₇H₁₆N₄O₃
• 分子量: 324.339
• InChiKey: PJBARLKWEGUQCW-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-Azidobenzoyl)-L-phenylalanine methyl ester 在 溶剂黄146 、 sodium iodide 作用下， 反应 12.0h， 以76%的产率得到(S)-3-benzyl-3,4-dihydro-1H-benzo[1,4]diazepine-2,5-dione
  参考文献：
  名称：

  One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

  摘要：

  Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.09.046
• 作为产物：
  描述：

  o-azidobenzoyl chloride 、 L-苯丙氨酸甲酯盐酸盐 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-(2-Azidobenzoyl)-L-phenylalanine methyl ester
  参考文献：
  名称：

  One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones

  摘要：

  Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones. (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2004.09.046

文献信息

• Facile Synthesis of 1,4-Benzodiazepin-5-one Derivatives via Intramolecular Aza-Wittig Reaction. Application to an Efficient Synthesis of O-Benzyl DC-81
  作者：Shoji Eguchi、Keizo Yamashita、Yuji Matsushita、Akikazu Kakehi

  DOI：10.1021/jo00118a016

  日期：1995.6

  The tandem Staudinger/aza-Wittig reaction of N-(o-azidobenzoyl)-alpha-amino acid esters gave the corresponding 1,4-benzodiazepin-5-one derivatives in moderate to good yields. This method was applied successfully to a new efficient synthesis of BzlDC-81.
• One pot conversion of azido arenes to N-arylacetamides and N-arylformamides: synthesis of 1,4-benzodiazepine-2,5-diones and fused [2,1-b]quinazolinones
  作者：Ahmed Kamal、A. Venkata Ramana、K. Srinivasa Reddy、K. Venkata Ramana、A. Hari Babu、B. Rajendra Prasad

  DOI：10.1016/j.tetlet.2004.09.046

  日期：2004.10

  Sodium iodide in acidic media has been employed for the synthesis of N-arylformamides and N-arylacetamides. The NaI/acetic acid reagent system has also been extended for the synthesis of 1,4-benzodiazepine-2,5-diones, pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones, and fused [2,1-b]quinazolinones. (C) 2004 Published by Elsevier Ltd.