allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-10-desacetoxyceph-3-em-4-carboxylate | 124876-47-7

• 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-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]-5λ6-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 124876-47-7
• 化学式: C₁₉H₂₀N₂O₇S
• 分子量: 420.443
• InChiKey: HWLXQVRHGFNOPS-CRAIPNDOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.15
• 重原子数：
  29.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  119.08
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-10-desacetoxyceph-3-em-4-carboxylate 在 盐酸二甲胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 2.0h， 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
• 作为产物：
  描述：

  allyl (6R,7R) 7-phenoxyacetamido-10-desacetoxyceph-3-em-4-carboxylate 在 间氯过氧苯甲酸 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到allyl (6R,7R) 7-phenoxyacetamido-1,1-dioxo-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

• SPRY, D. O.;SNYDER, N. J.;PRESTON, D. A.;WU, CHYUN-YEN E., HETEROCYCLES, 29,(1989) N, C. 1107-1118
  作者：SPRY, D. O.、SNYDER, N. J.、PRESTON, D. A.、WU, CHYUN-YEN E.

  DOI：——

  日期：——