Menthyl bicyclo[2.2.1]hept-2-en-5-carboxylate | 7188-01-4

• 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: Menthyl bicyclo[2.2.1]hept-2-en-5-carboxylate
• 英文别名: [(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 7188-01-4；84235-35-8；84235-36-9；138752-03-1；138752-04-2
• 化学式: C₁₈H₂₈O₂
• 分子量: 276.419
• InChiKey: NUXWNOJUDXSANL-GTUADWAHSA-N

物化性质

• 沸点：
  350.0±21.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)
• 保留指数：
  1430

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Menthyl bicyclo[2.2.1]hept-2-en-5-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (2R)-endo-5-norbornene-2-methanol 、 exo-5-norbornene-2-methanol
  参考文献：
  名称：

  The effect of alumina on the Diels-Alder reactions of cyclopentadiene with menthyl acrylate and dimenthyl fumarate.

  摘要：

  Alumina catalyzes the Diels-Alder reactions of cyclopentadiene with optically active menthyl acrylate and dimenthyl fumarate. Significant diastereoselectivity is observed in each case.

  DOI：

  10.1016/s0957-4166(00)80026-9
• 作为产物：
  描述：

  丙烯酸-L-薄荷酯 、 环戊二烯 以 甲苯 为溶剂， 生成 Menthyl bicyclo[2.2.1]hept-2-en-5-carboxylate
  参考文献：
  名称：

  Fluorinated alcohols as solvents for diels-alder reactions of chiral acrylates

  摘要：

  Fluorinated alcohols increase the rates and endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (-)-menthyl and (-)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (-)-menthyl acrylate, but decreases it when the dienophile is (-)-8-phenylmethyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.

  DOI：

  10.1016/s0957-4166(00)80368-7

文献信息

• A reinvestigation of asymmetric induction in diels-alder reactions to chiral acrylates.
  作者：Wolfgang Oppolzer、Mark Kurth、Daniel Reichlin、Frank Moffatt

  DOI：10.1016/s0040-4039(01)90516-7

  日期：1981.1

  The chiral induction in the Diels-Alder addition 1 → 2, assessed reliably by 19F-NMR-spectroscopy of the endo-esters 4, varied between 47 - 93% in favor of the 2-(R)-adducts 2 depending on the auxiliary chiral group and the Lewis-acid catalyst.

  的手性诱导的狄尔斯-阿德耳加成1→2，通过可靠地评估19所述的F-NMR光谱内切-酯4，47之间变化-赞成2-（R）93％2取决于-adducts辅助手性基团和路易斯酸催化剂。
• The effect of alumina on the Diels-Alder reactions of cyclopentadiene with menthyl acrylate and dimenthyl fumarate.
  作者：George W. Kabalka、Richard M. Pagni、Satinder Bains、George Hondrogiannis、Miechelle Plesco、Robert Kurt、Danielle Cox、James Green

  DOI：10.1016/s0957-4166(00)80026-9

  日期：1991.1

  Alumina catalyzes the Diels-Alder reactions of cyclopentadiene with optically active menthyl acrylate and dimenthyl fumarate. Significant diastereoselectivity is observed in each case.
• Fluorinated alcohols as solvents for diels-alder reactions of chiral acrylates
  作者：Curlos Cativiela、José I. García、José A. Mayoral、Ana.J. Royo、L. Salvatella

  DOI：10.1016/s0957-4166(00)80368-7

  日期：1993.7

  Fluorinated alcohols increase the rates and endo/exo selectivities of the Diels-Alder reactions of cyclopentadiene with (-)-menthyl and (-)-8-phenylmenthyl acrylates. The use of fluorinated alcohols also increases the diastereofacial selectivity in the reactions of (-)-menthyl acrylate, but decreases it when the dienophile is (-)-8-phenylmethyl acrylate. These facts are accounted for by the conformational preferences of the dienophile in non-HBD solvents and by the tendency of fluorinated alcohols to shift the conformational equilibrium towards the s-trans conformation.