(1S,2R)-1-Cyano-2-phenyl-1-cyclohexanecarboxylic acid | 162272-51-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,2R)-1-Cyano-2-phenyl-1-cyclohexanecarboxylic acid
• 英文别名: (1S,2R)-1-cyano-2-phenylcyclohexane-1-carboxylic acid
• CAS: 162272-51-7
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: KKZCNVRAIFUCQU-TZMCWYRMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-Cyano-2-phenyl-1-cyclohexanecarboxylic acid 在 sodium azide 、 五氯化磷 作用下， 以 乙醚 、 水 、 丙酮 为溶剂， 反应 3.0h， 生成 (1S,2R)-1-Cyano-2-phenyl-cyclohexanecarbonyl azide
  参考文献：
  名称：

  苯丙氨酸反式环己烷类似物的合成与制备拆分

  摘要：

  通过外消旋途径合成对映体纯的 (1R,2S)- 和 (1S,2R)-1-氨基-2-苯基环己烷甲酸 (trans-c6Phe) 的不同方法，然后是外消旋前体的半制备型 HPLC学习了。与 Diels-Alder 路线相比，Strecker 反应的完全非对映选择性和随后转化为氨基酸的高效率有利于这种方法。氨基酸及其前体的相对立体化学已被明确指定。最终的对映体纯氨基酸及其相应的 N-Boc 衍生物的制备是通过使用纤维素衍生的手性固定相对中间体之一进行 HPLC 拆分来进行的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400275
• 作为产物：
  描述：

  (1S,6R)-1-Cyano-6-phenyl-3-cyclohexene-1-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (1S,2R)-1-Cyano-2-phenyl-1-cyclohexanecarboxylic acid
  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.
• Synthesis and Preparative Resolution of thetrans-Cyclohexane Analogues of Phenylalanine
  作者：Carlos Cativiela、Pilar López、Marta Lasa

  DOI：10.1002/ejoc.200400275

  日期：2004.9

  enantiomerically pure (1R,2S)- and (1S,2R)-1-amino-2-phenylcyclohexanecarboxylic acids (trans-c6Phe) through a racemic pathway followed by semi-preparative HPLC of a racemic precursor have been studied. The complete diastereoselectivity of the Strecker reaction and the high efficiency of the subsequent transformations into the amino acid favour this method in comparison to the Diels−Alder route. The relative stereochemistry

  通过外消旋途径合成对映体纯的 (1R,2S)- 和 (1S,2R)-1-氨基-2-苯基环己烷甲酸 (trans-c6Phe) 的不同方法，然后是外消旋前体的半制备型 HPLC学习了。与 Diels-Alder 路线相比，Strecker 反应的完全非对映选择性和随后转化为氨基酸的高效率有利于这种方法。氨基酸及其前体的相对立体化学已被明确指定。最终的对映体纯氨基酸及其相应的 N-Boc 衍生物的制备是通过使用纤维素衍生的手性固定相对中间体之一进行 HPLC 拆分来进行的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)