(1R,2S,4R)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether | 136205-74-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (1R,2S,4R)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether
• 英文别名: Qvultrzxipfibg-guykvmemsa-；[(1S,2R,3S,4R)-3-(2,2-dimethylpropoxy)-4,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] (1R,2S,4R)-2-acetamidobicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 136205-74-8
• 化学式: C₂₅H₃₉NO₄
• 分子量: 417.589
• InChiKey: QVULTRZXIPFIBG-GUYKVMEMSA-N

物化性质

• 沸点：
  520.8±50.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4R)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以60%的产率得到(1R)-2-乙酰氨基双环[2.2.1]庚-5-烯-2-羧酸
  参考文献：
  名称：

  Asymmetric synthesis of 2-exo-aminonorbornane-2-endo-carboxylic acid derivatives

  摘要：

  The Diels-Alder reaction of cyclopentadiene with N-acetyl-alpha,beta-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position. So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-alpha,beta-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.

  DOI：

  10.1016/s0957-4166(00)82170-9
• 作为产物：
  描述：

  N-acetyl-α,β-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether 、 环戊二烯 在 四氯化钛 作用下， 以 甲苯 为溶剂， 反应 4.0h， 生成 (1S,2S,4S)-2-endo-acetamidobicyclo<2.2.1>hept-5-ene-2-exo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether 、 (1R,2S,4R)-2-exo-acetamidobicyclo<2.2.1>hept-5-ene-2-endo-carboxylate of (-)-cis-3-hydroxy isobornyl neopentyl ether
  参考文献：
  名称：

  Asymmetric synthesis of 2-exo-aminonorbornane-2-endo-carboxylic acid derivatives

  摘要：

  The Diels-Alder reaction of cyclopentadiene with N-acetyl-alpha,beta-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position. So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-alpha,beta-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.

  DOI：

  10.1016/s0957-4166(00)82170-9

文献信息

• Asymmetric synthesis of 2-exo-aminonorbornane-2-endo-carboxylic acid derivatives
  作者：Carlos Cativiela、Pilar López、José A. Mayoral

  DOI：10.1016/s0957-4166(00)82170-9

  日期：1991.1

  The Diels-Alder reaction of cyclopentadiene with N-acetyl-alpha,beta-didehydroalaninate of (-)-cis-3-hydroxy isobornyl neopentyl ether yields the corresponding 2-endo(exo)-acetamido-5-norbornene-2-exo(endo)-carboxylates with total diastereofacial selectivity and with a preference for the cycloadduct with the ester group placed at the endo position. So this dienophile is complementary with the previously described (-)-menthyl N-acetyl-alpha,beta-didehydroalaninate for the asymmetric synthesis of 2-aminonorbornane-2-carboxylic acids, since with the latter dienophile exo cycloadducts are preferably obtained with a high diastereofacial selectivity.