(2S)-2-amino-2-cyclohexylacetamide hydrochloride | 143118-45-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-amino-2-cyclohexylacetamide hydrochloride
• 英文别名: (2S)-2-amino-2-cyclohexylacetamide;hydrochloride
• CAS: 143118-45-0
• 化学式: C₈H₁₆N₂O*ClH
• 分子量: 192.689
• InChiKey: CQJQATMVIIXVNL-FJXQXJEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  12.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  69.11
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2S)-2-amino-2-cyclohexylacetamide hydrochloride 在 tris-(dibenzylideneacetone)dipalladium(0) 、 potassium carbonate 、 caesium carbonate 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 potassium iodide 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Amine-Catalyzed Asymmetric (3 + 3) Annulations of β′-Acetoxy Allenoates: Enantioselective Synthesis of 4H-Pyrans

  摘要：

  The asymmetric (3 + 3) annulations of beta'-acetoxy allenoates with either 3-oxo-nitriles or pyrazolones have been realized by using 6'-deoxy-6'-[(L)-N,N-(2,2'-oxidiethyl)-valine amido]quinine (6h) as the catalyst. The three functions of catalyst 6h, including Lewis base (quinuclidine N), H-bond donor (amide NH), and Bronsted base (morpholine N), cooperatively take crucial roles on the chemo- and enantioselectivity, allowing for the construction of 4H-pyran and 4H-pyrano[2,3-c]pyrazole in high yields and enantioselectivity.

  DOI：

  10.1021/jacs.6b04935
• 作为产物：
  描述：

  (S)-Amino-cyclohexyl-acetonitrile; hydrochloride 在 盐酸 作用下， 反应 18.0h， 生成 (2S)-2-amino-2-cyclohexylacetamide hydrochloride
  参考文献：
  名称：

  A convenient synthesis of (S)-2-Azidonitriles, (S)-2-aminonitriles and (S)-1,2-diamines

  摘要：

  (S)-2-Azidonitriles (S)-4 are easily accessible from (R)-2-(sulfonyloxy)nitriles (R)-2 by nucleophilic substitution with alkali azides 3 under complete inversion of configuration. The azidonitriles (S)-4 can be converted by catalytic hydrogenation into (S)-2-aminonitriles (S)-8 and by hydrogenation using LiAlH4 into (S)-1, 2-diaminoalkanes (S)-9, respectively, both, (S)-8 and (S)-9, isolated as hydrochlorides. Hydrolysis of the aminonitrile hydrochlorides (S)-8 HCl in a saturated solution of HC1 in alcohol gives (S)-2-amino carboxamide hydrochlorides(S)-10 . HCl with enantiomeric excesses >99% after recrystallization.

  DOI：

  10.1016/0957-4166(96)00044-4

文献信息

• Design and synthesis of HIV protease inhibitors. Variations of the carboxyterminus of the HIV protease inhibitor L-682,679
  作者：S. Jane DeSolms、Elizabeth A. Giuliani、James P. Guare、Joseph P. Vacca、William M. Sanders、Samuel L. Graham、J. Mark Wiggins、Paul L. Darke、Irving S. Sigal

  DOI：10.1021/jm00113a025

  日期：1991.9

  A series of tetrapeptide analogues of 1 (L-682,679), in which the carboxy terminus has been shortened and modified, was prepared and their inhibitory activity measured against the HIV protease in a peptide cleavage assay. Selected examples were tested as inhibitors of virus spread in cell culture. Compound 12 was a 10-fold more potent enzyme inhibitor than 1 in vitro and 30-fold more potent in inhibiting the viral spread in cells.