(R)-3-(3-cyclopentyloxy-4-methoxyphenyl)pentanedioic acid monobenzyl ester | 1427298-75-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: (R)-3-(3-cyclopentyloxy-4-methoxyphenyl)pentanedioic acid monobenzyl ester
• 英文别名: (3R)-3-(3-cyclopentyloxy-4-methoxyphenyl)-5-oxo-5-phenylmethoxypentanoic acid
• CAS: 1427298-75-6
• 化学式: C₂₄H₂₈O₆
• 分子量: 412.483
• InChiKey: VYUFBJNDLUXSRA-LJQANCHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-3-(3-cyclopentyloxy-4-methoxyphenyl)pentanedioic acid monobenzyl ester 在 盐酸 、 叠氮磷酸二苯酯 、 水 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 0.5h， 生成 (R)-(-)-咯利普兰
  参考文献：
  名称：

  A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization

  摘要：

  A highly enantioselective metal-free synthesis of both enantiomers of Rolipram is reported. The key stereoinductive step is a cinchona alkaloid catalyzed opening of a cyclic anhydride prepared from isovanillin, where both enantiomers are available using the same chiral catalyst in two protocols. An extended one-pot Curtius sequence provides the lactam directly from the desymmetrization product after enrichment in high yield and excellent ee. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.009
• 作为产物：
  描述：

  3-环戊氧-4-甲氧基苯甲醛 在 哌啶 、 水 、 奎尼丁 、 乙酸酐 、 potassium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 312.5h， 生成 (R)-3-(3-cyclopentyloxy-4-methoxyphenyl)pentanedioic acid monobenzyl ester
  参考文献：
  名称：

  A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization

  摘要：

  A highly enantioselective metal-free synthesis of both enantiomers of Rolipram is reported. The key stereoinductive step is a cinchona alkaloid catalyzed opening of a cyclic anhydride prepared from isovanillin, where both enantiomers are available using the same chiral catalyst in two protocols. An extended one-pot Curtius sequence provides the lactam directly from the desymmetrization product after enrichment in high yield and excellent ee. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.009

文献信息

• A simple enantioselective route toward (R)- and (S)-Rolipram via anhydride desymmetrization
  作者：Trpimir Ivšić、Zdenko Hameršak

  DOI：10.1016/j.tetasy.2013.01.009

  日期：2013.2

  A highly enantioselective metal-free synthesis of both enantiomers of Rolipram is reported. The key stereoinductive step is a cinchona alkaloid catalyzed opening of a cyclic anhydride prepared from isovanillin, where both enantiomers are available using the same chiral catalyst in two protocols. An extended one-pot Curtius sequence provides the lactam directly from the desymmetrization product after enrichment in high yield and excellent ee. (C) 2013 Elsevier Ltd. All rights reserved.