(1R*,2R*)-1-acetyl-2-methyl-3-cyclohexen-1-yl p-nitrobenzoate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R*,2R*)-1-acetyl-2-methyl-3-cyclohexen-1-yl p-nitrobenzoate
• 英文别名: [(1R,2R)-1-acetyl-2-methylcyclohex-3-en-1-yl] 4-nitrobenzoate
• 化学式: C₁₆H₁₇NO₅
• 分子量: 303.315
• InChiKey: JERFTFURIFNBHD-BDJLRTHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R*,2R*)-1-acetyl-2-methyl-3-cyclohexen-1-yl p-nitrobenzoate 在 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 以70%的产率得到(1R*,2R*)-1-acetyl-2-methyl-3-cyclohexen-1-ol
  参考文献：
  名称：

  Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one asa diels-alder ketene equivalent for the synthesisof γ-hydroxycyclohexenones

  摘要：

  A short and regioselective synthesis of gamma-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding gamma-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00928-x
• 作为产物：
  描述：

  间戊二烯 、 3-(p-nitrobenzoyloxy)-3-buten-2-one 在 三氯化铝 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以85%的产率得到(1R*,2R*)-1-acetyl-2-methyl-3-cyclohexen-1-yl p-nitrobenzoate
  参考文献：
  名称：

  Captodative olefin 3-p-nitrobenzoyloxy-3-buten-2-one asa diels-alder ketene equivalent for the synthesisof γ-hydroxycyclohexenones

  摘要：

  A short and regioselective synthesis of gamma-hydroxycyclohexenones is described, using 3-p-nitrobenzoyloxy-3-buten-2-one (2a) as a ketene equivalent in Diels-Alder reactions with substituted dienes. Oxidation with MCPBA of the alpha-acetylcyclohexenol derivative, obtained by hydrolysis of the cycloadducts, led to the corresponding gamma-hydroxycyclohexenones in moderate overall yields. Evidence of the mechanism is provided. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00928-x