N-(benzyloxycarbonyl)-(Z)-2,3-methanoleucine | 123311-19-3

• 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: N-(benzyloxycarbonyl)-(Z)-2,3-methanoleucine
• 英文别名: (1S,2S)-1-(phenylmethoxycarbonylamino)-2-propan-2-ylcyclopropane-1-carboxylic acid
• CAS: 123311-19-3
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: UDBHSOJQFLLWSL-WFASDCNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-(Z)-2,3-methanoleucine 在 1-羟基苯并三唑 、 戴斯-马丁氧化剂 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 生成 [(1S,2S)-1-((S)-1-Benzyl-2-oxo-2-phenethylcarbamoyl-ethylcarbamoyl)-2-isopropyl-cyclopropyl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Synthesis and calpain inhibitory activity of α-ketoamides with 2,3-methanoleucine stereoisomers at the P2 position

  摘要：

  A series of novel ketoamides incorporating all four 2,3-methanoleucine stereoisomers at the P-2 position was synthesized. The compounds displayed a wide variation in K-i values for inhibition of calpain I depending on the configuration of the P-2 methanoleucine residue. However, similar variation in cathepsin B inhibition was not observed suggesting that the S-2 pocket of calpain I is more stereosensitive than that of cathepsin B. (C) 2000 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(00)00518-7
• 作为产物：
  描述：

  N-(benzyloxycarbonyl)-(Z)-2,3-methanoleucine p-nitrobenzyl ester 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以35.4%的产率得到N-(benzyloxycarbonyl)-(Z)-2,3-methanoleucine
  参考文献：
  名称：

  Synthesis of (.+-.)-2,3-methanovaline and (.+-.)-2,3-methanoleucine

  摘要：

  DOI：

  10.1021/jo00286a015

文献信息

• Synthesis and calpain inhibitory activity of α-ketoamides with 2,3-methanoleucine stereoisomers at the P2 position
  作者：Isaac O Donkor、Xiaozhang Zheng、Duane D Miller

  DOI：10.1016/s0960-894x(00)00518-7

  日期：2000.11

  A series of novel ketoamides incorporating all four 2,3-methanoleucine stereoisomers at the P-2 position was synthesized. The compounds displayed a wide variation in K-i values for inhibition of calpain I depending on the configuration of the P-2 methanoleucine residue. However, similar variation in cathepsin B inhibition was not observed suggesting that the S-2 pocket of calpain I is more stereosensitive than that of cathepsin B. (C) 2000 Published by Elsevier Science Ltd.
• Synthesis of (.+-.)-2,3-methanovaline and (.+-.)-2,3-methanoleucine
  作者：V. P. Srivastava、Malcolm Roberts、Timothy Holmes、Charles H. Stammer

  DOI：10.1021/jo00286a015

  日期：1989.12