(R)-Pantolactone (1S,6R)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (R)-Pantolactone (1S,6R)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1S,6R)-1-cyano-6-phenylcyclohex-3-ene-1-carboxylate
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: PFDBGMLOSWHBNK-GQIGUUNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (E)-2-cyanocinnamate of (S)-ethyl lactate 在 四氯化钛 4-二甲氨基吡啶 、 氢氧化钾 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 108.0h， 生成 (R)-Pantolactone (1S,6R)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate
  参考文献：
  名称：

  Asymmetric Diels-Alder Reactions of Chiral (E)-2-Cyanocinnamates. 2. Synthesis of the Four 1-Amino-2-phenyl-1-cyclohexanecarboxylic Acids in Enantiomerically Pure Form

  摘要：

  High and complementary diastereoselectivities were obtained in the asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with butadiene when (S)-ethyl lactate and (R)-pantolactone were used as chiral auxiliaries in the presence of TiCl4. The most selective reactions allowed the synthesis of the cycloadducts 2a and 3b, whose absolute configurations were assigned by an X-ray diffraction study of diastereoisomer 3b. The hydrolysis and subsequent hydrogenation of the stereoisomers gave the corresponding enantiomeric cyanocarboxylic acids. From these products the four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids were synthesized in enantiomerically pure form following a protocol with stereocontrolled and stereodivergent transformations.

  DOI：

  10.1021/jo00104a038

文献信息

• Cativiela Carlos, Avenoza Alberto, Paris Miguel, Peregrina Jesus M., J. Org. Chem, 59 (1994) N 25, S 7774-7778
  作者：Cativiela Carlos, Avenoza Alberto, Paris Miguel, Peregrina Jesus M.

  DOI：——

  日期：——
• Asymmetric Diels-Alder Reactions of Chiral (E)-2-Cyanocinnamates. 2. Synthesis of the Four 1-Amino-2-phenyl-1-cyclohexanecarboxylic Acids in Enantiomerically Pure Form
  作者：Carlos Cativiela、Alberto Avenoza、Miguel Paris、Jesus M. Peregrina

  DOI：10.1021/jo00104a038

  日期：1994.12

  High and complementary diastereoselectivities were obtained in the asymmetric Diels-Alder reactions of chiral (E)-2-cyanocinnamates with butadiene when (S)-ethyl lactate and (R)-pantolactone were used as chiral auxiliaries in the presence of TiCl4. The most selective reactions allowed the synthesis of the cycloadducts 2a and 3b, whose absolute configurations were assigned by an X-ray diffraction study of diastereoisomer 3b. The hydrolysis and subsequent hydrogenation of the stereoisomers gave the corresponding enantiomeric cyanocarboxylic acids. From these products the four 1-amino-2-phenyl-1-cyclohexanecarboxylic acids were synthesized in enantiomerically pure form following a protocol with stereocontrolled and stereodivergent transformations.