allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate | 113599-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: prop-2-enyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-4-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 113599-78-3
• 化学式: C₃₀H₂₇ClN₂O₄
• 分子量: 515.008
• InChiKey: MNLSBRJGWXWHCC-RSXGOPAZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  67.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate 在 碳酸氢钠 、 对甲苯磺酸 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 乙酸乙酯 为溶剂， 反应 22.0h， 生成 allyl (6S,7S)-7-<<(R)-N-<(allyloxy)carbonyl>-2-(4-hydroxyphenyl)glycyl>amino>-3-(chloromethyl)-8-oxo-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  An examination of O-2-isocephems as orally absorbable antibiotics

  摘要：

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.

  DOI：

  10.1021/jm00401a020
• 作为产物：
  描述：

  烯丙基2-溴乙酸乙酯 在 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 溶剂黄146 、 三苯基膦 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 生成 allyl (6S,7S)-3-(chloromethyl)-8-oxo-7-(tritylamino)-1-aza-4-oxabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  常规的对映选择性O-2-异佛烯酮的合成

  摘要：

  描述了用于将容易获得的手性氮杂环丁酮（2）转化为O-2-异头孢烯（5）的简单程序。

  DOI：

  10.1039/c39870001283

文献信息

• A general enantioselective O-2-isocephem synthesis
  作者：Harold Mastalerz、Vivianne Vinet

  DOI：10.1039/c39870001283

  日期：——

  A simple procedure for the conversion of the readily available chiral azetidinone (2) into the O-2-isocephem (5) is described.

  描述了用于将容易获得的手性氮杂环丁酮（2）转化为O-2-异头孢烯（5）的简单程序。
• MASTALERZ, HAROLD;MENARD, MARCEL;VINET, VIVIANNE;DESIDERIO, JAMES;FUNG-TO+, J. MED. CHEM., 31,(1988) N 6, 1190-1196
  作者：MASTALERZ, HAROLD、MENARD, MARCEL、VINET, VIVIANNE、DESIDERIO, JAMES、FUNG-TO+

  DOI：——

  日期：——
• An examination of O-2-isocephems as orally absorbable antibiotics
  作者：Harold Mastalerz、Marcel Menard、Vivianne Vinet、James Desiderio、Joan Fung-Tomc、Robert Kessler、Yuan Tsai

  DOI：10.1021/jm00401a020

  日期：1988.6

  The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described. These compounds possessed a D-[(p-hydroxyphenyl)glycyl]amino substituent at the 7-position while the substituent at the 3-position was varied. Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms. Against Gram-negative organisms, their activity was variable but did indicate a lower beta-lactamase stability. Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.
• Design, synthesis and antibacterial activities of a series of new 2-oxaisocephems
  作者：Jianbo Wu、Xueying Wu、Fan Lei、Huajie Yuan、Li Hai、Yong Wu

  DOI：10.1016/j.bmcl.2012.06.040

  日期：2012.8

  A series of 2-oxaisocephems with a thio-substituted methyl group at the 3-position and a [2-(5-amino-1,2,4-thiadizol-3-yl)-2-(Z)-alkoxyimino]acetamido moiety at 7-position were synthesized and tested for their antibacterial activities. The analogs 17c and 17f have well-balanced potency and significantly enhanced activity as compared with the reference compound ceftazidime. (C) 2012 Elsevier Ltd. All rights reserved.