7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid | 37794-96-0

• 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: 7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid
• 英文别名: (6R,7R)-3-methylidene-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]octane-2-carboxylic acid
• CAS: 37794-96-0
• 化学式: C₁₆H₁₆N₂O₄S
• 分子量: 332.38
• InChiKey: QWVFKWCHCHJQQD-ILWWEHDPSA-N

物化性质

• 沸点：
  693.5±55.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid 在 吡啶 、 三甲基氯硅烷 作用下， 反应 24.0h， 生成 7-苯乙酰胺基-3-甲基-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸
  参考文献：
  名称：

  A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media

  摘要：

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00512-8
• 作为产物：
  描述：

  4-methoxybenzyl 7β-phenylacetamido-3-methylenecepham-4-carboxylate 在 盐酸 作用下， 以 various solvent(s) 为溶剂， 反应 1.0h， 以78%的产率得到7-(phenylacetamido)-3-exo-methylenecepham-4-carboxylic acid
  参考文献：
  名称：

  Deprotection of carboxylic esters of .beta.-lactam homologs. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix

  摘要：

  p-Methoxybenzyl, diphenylmethyl, and tert-butyl esters were deprotected by gentle heating in phenol. This method of ester cleavage played an important role in beta-lactam synthesis. The mechanism of the reaction is believed to involve a proton relay through a hydrogen-bonded phenolic matrix.

  DOI：

  10.1021/jo00011a034

文献信息

• TORII, SIGERU;TANAKA, HIDEO;TANIGUCHI, MASATOSHI;KAMEYAMA, YUTAKA;SASAOKA+, J. ORG. CHEM., 56,(1991) N1, C. 3633-3637
  作者：TORII, SIGERU、TANAKA, HIDEO、TANIGUCHI, MASATOSHI、KAMEYAMA, YUTAKA、SASAOKA+

  DOI：——

  日期：——
• US4013650A
  申请人：——

  公开号：US4013650A

  公开（公告）日：1977-03-22
• Deprotection of carboxylic esters of .beta.-lactam homologs. Cleavage of p-methoxybenzyl, diphenylmethyl, and tert-butyl esters effected by a phenolic matrix
  作者：Sigeru Torii、Hideo Tanaka、Masatoshi Taniguchi、Yutaka Kameyama、Michio Sasaoka、Takashi Shiroi、Ryo Kikuchi、Ichiro Kawahara、Akihiro Shimabayashi、Shigemitsu Nagao

  DOI：10.1021/jo00011a034

  日期：1991.5

  p-Methoxybenzyl, diphenylmethyl, and tert-butyl esters were deprotected by gentle heating in phenol. This method of ester cleavage played an important role in beta-lactam synthesis. The mechanism of the reaction is believed to involve a proton relay through a hydrogen-bonded phenolic matrix.
• A facile synthesis of 7-amino-3-desacetoxycephalosporanic acid derivatives by indium-mediated reduction of 3-iodomethylcephems in aqueous media
  作者：Hyungsun Chae、Sangwon Cho、Gyochang Keum、Soon Bang Kang、Ae Nim Pae、Youseung Kim

  DOI：10.1016/s0040-4039(00)00512-8

  日期：2000.5

  An efficient reductive conversion of 3-iodomethylcephalosporin and 3-acetoxymethylcephalosporin derivatives mediated by indium into the corresponding 3-methylcephems and 3-methylenecephams in moderate to good yields has been developed in an aqueous system. 3-Methylenecephams are converted into the corresponding 3-methylcephems under previously reported basic conditions quantitatively. (C) 2000 Elsevier Science Ltd. All rights reserved.