6-Diazo-7-oxo-octanoic acid ethyl ester | 251362-18-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-Diazo-7-oxo-octanoic acid ethyl ester
• 英文别名: Ethyl 6-diazo-7-oxooctanoate；ethyl 6-diazo-7-oxooctanoate
• CAS: 251362-18-2
• 化学式: C₁₀H₁₆N₂O₃
• 分子量: 212.249
• InChiKey: DRCDECHMGUYOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-Diazo-7-oxo-octanoic acid ethyl ester 在 咪唑 、 4-二甲氨基吡啶 、 双(三甲基硅烷基)氨基钾 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 15.33h， 生成 ethyl (10E,12E)-9-[tert-butyl(diphenyl)silyl]oxy-6-diazo-7-oxooctadeca-10,12-dienoate
  参考文献：
  名称：

  Synthesis of 2,3-Dinor-5,6-dihydro-15F_2t-isoprostane

  摘要：

  A concise synthesis of the 15-F-2t-isoprostane urinary metabolite 2, a potential marker for systemic oxidative stress, is described. This synthesis confirmed the structure of this important product of human metabolism. The key transformation is the rhodium-mediated diastereoselective cyclization of diazo ketone 4, followed by cyclopropane ring opening with thiophenol and Lewis acid. Material prepared by the synthesis outlined here will be used to develop an antibody-based assay for clinically quantifying systemic oxidative stress.

  DOI：

  10.1021/jo9910738
• 作为产物：
  描述：

  ethyl 6-benzoyl-7-oxooctanoate 在 p-nitrobenzenesulfonyl azide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以61%的产率得到6-Diazo-7-oxo-octanoic acid ethyl ester
  参考文献：
  名称：

  Synthesis of 2,3-Dinor-5,6-dihydro-15F_2t-isoprostane

  摘要：

  A concise synthesis of the 15-F-2t-isoprostane urinary metabolite 2, a potential marker for systemic oxidative stress, is described. This synthesis confirmed the structure of this important product of human metabolism. The key transformation is the rhodium-mediated diastereoselective cyclization of diazo ketone 4, followed by cyclopropane ring opening with thiophenol and Lewis acid. Material prepared by the synthesis outlined here will be used to develop an antibody-based assay for clinically quantifying systemic oxidative stress.

  DOI：

  10.1021/jo9910738

文献信息

• Synthesis of 2,3-Dinor-5,6-dihydro-15F_2t-isoprostane
  作者：Douglass F. Taber、Kazuo Kanai

  DOI：10.1021/jo9910738

  日期：1999.10.1

  A concise synthesis of the 15-F-2t-isoprostane urinary metabolite 2, a potential marker for systemic oxidative stress, is described. This synthesis confirmed the structure of this important product of human metabolism. The key transformation is the rhodium-mediated diastereoselective cyclization of diazo ketone 4, followed by cyclopropane ring opening with thiophenol and Lewis acid. Material prepared by the synthesis outlined here will be used to develop an antibody-based assay for clinically quantifying systemic oxidative stress.