(R)-Pantolactone (1R,6S)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate | 162272-49-3

• 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 (1R,6S)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate
• 英文别名: [(3R)-4,4-dimethyl-2-oxooxolan-3-yl] (1R,6S)-1-cyano-6-phenylcyclohex-3-ene-1-carboxylate
• CAS: 162272-49-3
• 化学式: C₂₀H₂₁NO₄
• 分子量: 339.391
• InChiKey: PFDBGMLOSWHBNK-FTRWYGJKSA-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

• 作为反应物：
  描述：

  (R)-Pantolactone (1R,6S)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate 在 palladium on activated charcoal 氢氧化钾 、 sodium azide 、 五氯化磷 、 氢气 作用下， 以 乙醚 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 (1R,2S)-1-Cyano-2-phenyl-cyclohexanecarbonyl azide
  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
• 作为产物：
  描述：

  (E)-2-cyanocinnamate of (R)-pantolactone 、 1,3-丁二烯 在 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 (R)-Pantolactone (1R,6S)-1-cyano-6-phenyl-3-cyclohexene-1-carboxylate
  参考文献：
  名称：

  对映体纯形式的新型构象受限的α，α-二取代-β-氨基酸和β-内酰胺的合成

  摘要：

  光学活性的顺式- ， -图8a和8b中，和反式-1-氨基甲基-2-苯基环己烷-1-羧酸，图9a和9b中，制得使用第尔斯-阿尔德环加成与手性（E）由1,3-丁二烯开始-2 -氰基肉桂酸酯是关键步骤，并遵循立体控制反应的规程。这些构象受限的β-氨基酸的随后环化产生对映体纯形式的相应的α，α-二取代-β-内酰胺10a，10b，11a和11b。

  DOI：

  10.1016/0957-4166(95)00174-n

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.
• Synthesis of a new type of conformationally constrained α,α-disubstituted-β-amino acids and β-lactams in enantiomerically pure form
  作者：Alberto Avenoza、Carlos Cativiela、Miguel París、Jesús M. Peregrina

  DOI：10.1016/0957-4166(95)00174-n

  日期：1995.6

  e-1-carboxylic acids, 9a and 9b, were obtained starting from 1,3-butadiene using Diels-Alder cycloadditions with chiral (E)-2-cyanocinnamates as key steps and following a protocol of stereocontrolled reactions. Subsequent cyclization of these conformationally constrained β-amino acids led to the corresponding α,α-disubstituted-β-lactams 10a, 10b, 11a and 11b in enantiomerically pure forms.

  光学活性的顺式- ， -图8a和8b中，和反式-1-氨基甲基-2-苯基环己烷-1-羧酸，图9a和9b中，制得使用第尔斯-阿尔德环加成与手性（E）由1,3-丁二烯开始-2 -氰基肉桂酸酯是关键步骤，并遵循立体控制反应的规程。这些构象受限的β-氨基酸的随后环化产生对映体纯形式的相应的α，α-二取代-β-内酰胺10a，10b，11a和11b。