6β-(2,2,2-trichloro-ethoxycarbonylamino)-penicillanic acid | 35500-66-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: 6β-(2,2,2-trichloro-ethoxycarbonylamino)-penicillanic acid
• 英文别名: Penicillansaeure 4a；(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2,2,2-trichloroethoxycarbonylamino)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
• CAS: 35500-66-4
• 化学式: C₁₁H₁₃Cl₃N₂O₅S
• 分子量: 391.66
• InChiKey: FZQJQTMVCJMGJB-JCGDXUMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6β-(2,2,2-trichloro-ethoxycarbonylamino)-penicillanic acid 生成 ((5R)-2c-isocyanato-3,3-dimethyl-7-oxo-(5rH)-4-thia-1-aza-bicyclo[3.2.0]hept-6t-yl)-carbamic acid 2,2,2-trichloro-ethyl ester
  参考文献：
  名称：

  [来自青霉素的新的内酰胺系统]。

  摘要：

  Abstract3‐Isopropyl‐4‐thia‐2,6‐diazabicyclo[3.2.0]heptan‐7‐on (8), a potential intermediate for the synthesis of new β‐lactam antibiotics [5], was prepared from the urethanes 7a and 9 by reduction with zinc/acetic acid. The cyclic Schiff base 10, which constitutes an intermediate in this reaction, was prepared by reduction of 9 with CrCl2 and was further reduced to 8 with zinc/acetic acid.

  DOI：

  10.1002/hlca.19720550211
• 作为产物：
  描述：

  6-氨基青霉烷酸 、 氯甲酸-2,2,2-三氯乙酯 生成 6β-(2,2,2-trichloro-ethoxycarbonylamino)-penicillanic acid
  参考文献：
  名称：

  [来自青霉素的新的内酰胺系统]。

  摘要：

  Abstract3‐Isopropyl‐4‐thia‐2,6‐diazabicyclo[3.2.0]heptan‐7‐on (8), a potential intermediate for the synthesis of new β‐lactam antibiotics [5], was prepared from the urethanes 7a and 9 by reduction with zinc/acetic acid. The cyclic Schiff base 10, which constitutes an intermediate in this reaction, was prepared by reduction of 9 with CrCl2 and was further reduced to 8 with zinc/acetic acid.

  DOI：

  10.1002/hlca.19720550211

文献信息

• Neue ?-Lactamsysteme aus Penicillinen. Modifikationen von Antibiotika, 5. Mitteilung [1]
  作者：B. Fechtig、H. Bickel、K. Heusler

  DOI：10.1002/hlca.19720550211

  日期：1972.1.31

  Abstract3‐Isopropyl‐4‐thia‐2,6‐diazabicyclo[3.2.0]heptan‐7‐on (8), a potential intermediate for the synthesis of new β‐lactam antibiotics [5], was prepared from the urethanes 7a and 9 by reduction with zinc/acetic acid. The cyclic Schiff base 10, which constitutes an intermediate in this reaction, was prepared by reduction of 9 with CrCl2 and was further reduced to 8 with zinc/acetic acid.