Ethyl ε-diazo-α,4-dimethylbenzenehexanoate | 138573-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Ethyl ε-diazo-α,4-dimethylbenzenehexanoate
• 英文别名: Ethyl 2-diazo-6-(4-methylphenyl)heptanoate；ethyl 2-diazo-6-(4-methylphenyl)heptanoate
• CAS: 138573-09-8
• 化学式: C₁₆H₂₂N₂O₂
• 分子量: 274.363
• InChiKey: BPVRZQBCVBPMBR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl ε-diazo-α,4-dimethylbenzenehexanoate 在 吡啶 、 lithium aluminium tetrahydride 、 lithium diisopropyl amide 作用下， 反应 21.75h， 生成 (1R,2R)-tochuinyl acetate
  参考文献：
  名称：

  Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate

  摘要：

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.

  DOI：

  10.1021/jo00028a011
• 作为产物：
  描述：

  4-(4-甲基苯基)戊烷-1-醇 在 四溴化碳 、 四丁基碘化铵 、 sodium hydride 、 甲烷磺酰基叠氮化物 、 三苯基膦 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 54.17h， 生成 Ethyl ε-diazo-α,4-dimethylbenzenehexanoate
  参考文献：
  名称：

  Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate

  摘要：

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.

  DOI：

  10.1021/jo00028a011

文献信息

• Rhodium-mediated cyclopentane construction can compete with .beta.-hydride elimination: synthesis of (.+-.)-tochuinyl acetate
  作者：Douglass F. Taber、Michael J. Hennessy、James P. Louey

  DOI：10.1021/jo00028a011

  日期：1992.1

  Rhodium(II) carboxylate catalyzed C-H insertion to form a cyclopentane is shown to compete effectively with beta-hydride elimination, except when the beta-hydrogen is ternary. Cyclization of diazo ester 27 gives 28, which is converted in three steps to (+/-)-tochuinyl acetate 25. Both the cyclization to form 28 and the alkylation of 28 proceed with remarkable diastereoselectivity.