(E)-4-[Benzyloxycarbonyl-(2-chloro-butyryl)-amino]-but-2-enoic acid ethyl ester | 717132-77-9

• 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: (E)-4-[Benzyloxycarbonyl-(2-chloro-butyryl)-amino]-but-2-enoic acid ethyl ester
• CAS: 717132-77-9
• 化学式: C₁₈H₂₂ClNO₅
• 分子量: 367.829
• InChiKey: ZDELZJPPPQYYIW-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.29
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.91
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (E)-4-[Benzyloxycarbonyl-(2-chloro-butyryl)-amino]-but-2-enoic acid ethyl ester 在 dirhodium tetraacetate 、 氢氧化钾 、 偶氮二异丁腈 、 p-dodecylsulfonyl azide 、 TEA 、 三正丁基氢锡 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 、 甲苯 、 乙腈 为溶剂， 生成 (3R,3aR,6R,6aS)-3-Ethyl-2,5-dioxo-octahydro-cyclopenta[b]pyrrole-6-carboxylic acid 4-nitro-benzyl ester
  参考文献：
  名称：

  Design and synthesis of bridged γ-lactams as analogues of β-lactam antibiotics

  摘要：

  Anti-Bredt bridged bicyclo[3.2.1] gamma-lactams were designed as inhibitors of penicillin binding proteins (PBPs). The compounds were prepared by a carbenoid insertion into a lactam N-H bond. Their weak antibacterial activity could either be explained by a poor chemical stability or by unfavorable steric interactions of the methylene bridge of the gamma-lactam with the targeted enzymes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.004
• 作为产物：
  描述：

  N-(2-氧代乙基)氨基甲酸苄酯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 (E)-4-[Benzyloxycarbonyl-(2-chloro-butyryl)-amino]-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Design and synthesis of bridged γ-lactams as analogues of β-lactam antibiotics

  摘要：

  Anti-Bredt bridged bicyclo[3.2.1] gamma-lactams were designed as inhibitors of penicillin binding proteins (PBPs). The compounds were prepared by a carbenoid insertion into a lactam N-H bond. Their weak antibacterial activity could either be explained by a poor chemical stability or by unfavorable steric interactions of the methylene bridge of the gamma-lactam with the targeted enzymes. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.004