tert-butyl (1R,2S)-2-phenylcyclohexyl maleate | 162361-93-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (1R,2S)-2-phenylcyclohexyl maleate
• 英文别名: 4-O-tert-butyl 1-O-[(1R,2S)-2-phenylcyclohexyl] (Z)-but-2-enedioate
• CAS: 162361-93-5
• 化学式: C₂₀H₂₆O₄
• 分子量: 330.424
• InChiKey: PSWOQTHOISHGAB-IMIANULMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  tert-butyl (1R,2S)-2-phenylcyclohexyl maleate 在 氯化二乙基铝 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 43.0h， 生成 (1R,2S,3R,4S)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((1R,2S)-2-phenyl-cyclohexyl) ester
  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：

  (1R,2S)-trans-2-phenylcyclohexanol 在 硫酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 tert-butyl (1R,2S)-2-phenylcyclohexyl 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.