allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-phenylselenomethyl-10-desacetoxyceph-3-em-4-carboxylate | 300810-87-1

• 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: allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-phenylselenomethyl-10-desacetoxyceph-3-em-4-carboxylate
• 英文别名: prop-2-enyl (6R,7R)-3-methyl-5,5,8-trioxo-7-[(2-phenoxyacetyl)amino]-4-(phenylselanylmethyl)-5lambda6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；prop-2-enyl (6R,7R)-3-methyl-5,5,8-trioxo-7-[(2-phenoxyacetyl)amino]-4-(phenylselanylmethyl)-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 300810-87-1
• 化学式: C₂₆H₂₆N₂O₇SSe
• 分子量: 589.528
• InChiKey: PFTUNZIMUHCKPP-VPYMBCGJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.97
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  三正丁基氢锡 、 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-phenylselenomethyl-10-desacetoxyceph-3-em-4-carboxylate 在 偶氮二异丁腈 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-methyl-10-desacetoxyceph-3-em-4-carboxylate 、 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-tributylstannylmethyl-10-desacetoxyceph-3-em-4-carboxylate
  参考文献：
  名称：

  Radical Rearrangement: A Strategy for Conversion of Cephalosporin to 1-Carba(dethia)cephalosporin

  摘要：

  A radical rearrangement approach to semisynthesis of the carbacephem class of beta-lactam antibiotics is reported. The crucial bond construction in assembly of the carbacephem framework was accomplished by intramolecular C-C bond formation between an azetidin-2-one-4-yl and a pendant diene ester. This reactive intermediate was generated by fragmentation of a cephern derived radical followed by loss of sulfur dioxide. The radical precursor was prepared in 63% yield over four steps and the subsequent rearrangement reaction provided carbacephem products in a single step at 23% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00417-8
• 作为产物：
  描述：

  7-氨基-3-甲基-8-氧代-5-硫杂-1-氮杂双环[4.2.0]辛-2-烯-2-甲酸 在 sodium hydroxide 、 盐酸二甲胺 、 四丁基硫酸氢铵 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-2-phenylselenomethyl-10-desacetoxyceph-3-em-4-carboxylate
  参考文献：
  名称：

  Radical Rearrangement: A Strategy for Conversion of Cephalosporin to 1-Carba(dethia)cephalosporin

  摘要：

  A radical rearrangement approach to semisynthesis of the carbacephem class of beta-lactam antibiotics is reported. The crucial bond construction in assembly of the carbacephem framework was accomplished by intramolecular C-C bond formation between an azetidin-2-one-4-yl and a pendant diene ester. This reactive intermediate was generated by fragmentation of a cephern derived radical followed by loss of sulfur dioxide. The radical precursor was prepared in 63% yield over four steps and the subsequent rearrangement reaction provided carbacephem products in a single step at 23% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00417-8

文献信息

• Radical Rearrangement: A Strategy for Conversion of Cephalosporin to 1-Carba(dethia)cephalosporin
  作者：Noreen G. Halligan、Raymond F. Brown、Douglas O. Spry、Larry C. Blaszczak

  DOI：10.1016/s0040-4020(00)00417-8

  日期：2000.7

  A radical rearrangement approach to semisynthesis of the carbacephem class of beta-lactam antibiotics is reported. The crucial bond construction in assembly of the carbacephem framework was accomplished by intramolecular C-C bond formation between an azetidin-2-one-4-yl and a pendant diene ester. This reactive intermediate was generated by fragmentation of a cephern derived radical followed by loss of sulfur dioxide. The radical precursor was prepared in 63% yield over four steps and the subsequent rearrangement reaction provided carbacephem products in a single step at 23% yield. (C) 2000 Elsevier Science Ltd. All rights reserved.