tert-butyl l-menthyl maleate

• 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: tert-butyl l-menthyl maleate
• 英文别名: 4-O-tert-butyl 1-O-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] (Z)-but-2-enedioate
• 化学式: C₁₈H₃₀O₄
• 分子量: 310.434
• InChiKey: IDNGKNPXEHWESE-KBTARTEGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  环戊二烯 、 tert-butyl l-menthyl maleate 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以98%的产率得到
  参考文献：
  名称：

  Asymmetric Diels-Alder Reaction of Unsymmetrical Maleates. A Chemical Access to Chiral, Unsymmetrical cis-Cyclohexene-1,2-dicarboxylates

  摘要：

  A new route to optically active, unsymmetrical cis-cyclohexene-1,2-dicarboxylate derivatives has been developed on the basis of the asymmetric Diels-Alder reaction of chiral, unsymmetrical maleates catalyzed by certain Lewis acids. A notably high level of asymmetric induction has been observed in the asymmetric Diels-Alder reaction of unsymmetrical maleates possessing chiral auxiliaries such as alpha-phenethyl and trans-2-phenylcyclohexyl groups. The origin of the chiral outcome using these dienophiles has been elucidated.

  DOI：

  10.1021/ja00093a013
• 作为产物：
  描述：

  Maleinsaeure-mono-(1'R,3'R,4'S)-3-menthylester 、 异丁烯 在 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 tert-butyl l-menthyl maleate
  参考文献：
  名称：

  Asymmetric Diels-Alder Reaction of Unsymmetrical Maleates. A Chemical Access to Chiral, Unsymmetrical cis-Cyclohexene-1,2-dicarboxylates

  摘要：

  A new route to optically active, unsymmetrical cis-cyclohexene-1,2-dicarboxylate derivatives has been developed on the basis of the asymmetric Diels-Alder reaction of chiral, unsymmetrical maleates catalyzed by certain Lewis acids. A notably high level of asymmetric induction has been observed in the asymmetric Diels-Alder reaction of unsymmetrical maleates possessing chiral auxiliaries such as alpha-phenethyl and trans-2-phenylcyclohexyl groups. The origin of the chiral outcome using these dienophiles has been elucidated.

  DOI：

  10.1021/ja00093a013

文献信息

• Asymmetric Diels-Alder Reaction of Unsymmetrical Maleates. A Chemical Access to Chiral, Unsymmetrical cis-Cyclohexene-1,2-dicarboxylates
  作者：Keiji Maruoka、Matsujiro Akakura、Susumu Saito、Takashi Ooi、Hisashi Yamamoto

  DOI：10.1021/ja00093a013

  日期：1994.7

  A new route to optically active, unsymmetrical cis-cyclohexene-1,2-dicarboxylate derivatives has been developed on the basis of the asymmetric Diels-Alder reaction of chiral, unsymmetrical maleates catalyzed by certain Lewis acids. A notably high level of asymmetric induction has been observed in the asymmetric Diels-Alder reaction of unsymmetrical maleates possessing chiral auxiliaries such as alpha-phenethyl and trans-2-phenylcyclohexyl groups. The origin of the chiral outcome using these dienophiles has been elucidated.