(S)-benzoylamino-cyclohexyl-acetic acid | 145416-94-0

• 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: (S)-benzoylamino-cyclohexyl-acetic acid
• 英文别名: (S)-Benzoylamino-cyclohexyl-essigsaeure；(2S)-2-benzamido-2-cyclohexylacetic acid
• CAS: 145416-94-0
• 化学式: C₁₅H₁₉NO₃
• 分子量: 261.321
• InChiKey: WKPQZTYDNQZEQK-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-benzoylamino-cyclohexyl-acetic acid 在 palladium on activated charcoal 、 lithium aluminium tetrahydride 、 乙醚 、 草酸 作用下， 生成 L-环己基甘氨醇
  参考文献：
  名称：

  398.β-氨基醇的制备

  摘要：

  DOI：

  10.1039/jr9570002073
• 作为产物：
  描述：

  L-环己基甘氨酸 在 奎宁 作用下， 生成 (S)-benzoylamino-cyclohexyl-acetic acid
  参考文献：
  名称：

  398.β-氨基醇的制备

  摘要：

  DOI：

  10.1039/jr9570002073

文献信息

• Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis
  作者：Eiji Yamamoto、Kodai Wakafuji、Yuho Furutachi、Kaoru Kobayashi、Takashi Kamachi、Makoto Tokunaga

  DOI：10.1021/acscatal.8b00693

  日期：2018.7.6

  Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%)

  描述了用合成的小分子催化剂对α-手性酯的不对称碱水解。奎宁衍生的季铵盐用作手性相转移催化剂，可通过动态动力学拆分促进CHCl 3 / NaOH（aq）中N保护的氨基酸六氟异丙基酯的碱水解，以中等至良好的收率提供相应的产物（最高99％）和最高96：4 er。使用DFT计算和伪过渡态（pseudo-TS）构象搜索进行的实验和计算机制研究提供了考虑立体选择性起源的TS模型。该模型表明，π-堆积和H-键相互作用在稳定TS结构中起重要作用。
• Discovery of a series of novel compounds with moderate anti-hepatitis C virus NS3 protease activity in vitro
  作者：Fangyuan Shi、Yingjie Zhang、Wenfang Xu

  DOI：10.1016/j.bmc.2015.07.032

  日期：2015.9

  The hepatitis C virus (HCV) NS3/4A protease that plays an important role in the viral life cycle has been proven to be an excellent target for the discovery of anti-HCV drugs. Enlightened by some P2-triazole and amide compounds, which had been found as HCV NS3 protease inhibitors, we designed and synthesized a series of novel compounds by incorporating different amino acid residues in P1/P1' and P3/P3' position to develop novel antiviral agents. The result of enzyme inhibition assay indicated that all the designed compounds showed moderate anti-HCV NS3 protease activity. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. (C) 2015 Elsevier Ltd. All rights reserved.
• Pd-Catalyzed Enantioselective C–H Iodination: Asymmetric Synthesis of Chiral Diarylmethylamines
  作者：Ling Chu、Xiao-Chen Wang、Curtis E. Moore、Arnold L. Rheingold、Jin-Quan Yu

  DOI：10.1021/ja408864c

  日期：2013.11.6

  An enantioselective C-H iodination reaction using a mono-N-benzoyl-protected amino acid has been developed for the synthesis of chiral diarylmethylamines. The reaction uses iodine as the sole oxidant and proceeds at ambient temperature and under air.