2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile | 366013-96-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile
• 英文别名: (1R,2R,4S)-2-(2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]hept-2-yl)acetonitrile；(1R,2R)-2-cyanomethyl-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptane；2-[(1R,2R,4S)-2-hydroxy-1,3,3-trimethyl-2-bicyclo[2.2.1]heptanyl]acetonitrile
• CAS: 366013-96-9
• 化学式: C₁₂H₁₉NO
• 分子量: 193.289
• InChiKey: GZZUHNFXWZTLCG-WCQGTBRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile 在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (E)-3-(4-(N-(2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)ethyl)sulfamoyl)phenyl)acrylic acid
  参考文献：
  名称：

  Enantiopure antituberculosis candidates synthesized from (−)-fenchone

  摘要：

  The synthesis of new enantiopure N-acyl compounds derived from (-)-fenchone has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis H(37)Rv showed for most of them moderate activity. The structures bearing sulfonamide functionality have comparable activity to ethambutol and possess low cytotoxicity. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.025
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 、 乙腈 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.75h， 以99%的产率得到2-((1R,2R,4S)-2-hydroxy-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)acetonitrile
  参考文献：
  名称：

  Enantiopure antituberculosis candidates synthesized from (−)-fenchone

  摘要：

  The synthesis of new enantiopure N-acyl compounds derived from (-)-fenchone has been performed. The evaluation of their in vitro activity against Mycobacterium tuberculosis H(37)Rv showed for most of them moderate activity. The structures bearing sulfonamide functionality have comparable activity to ethambutol and possess low cytotoxicity. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.025

文献信息

• Unsaturated Nitriles:  Stereoselective MgO Eliminations
  作者：Fraser F. Fleming、Brian C. Shook

  DOI：10.1021/jo0162944

  日期：2002.5.1

  Alpha,beta-unsaturated nitriles are readily synthesized by eliminating MgO from beta-hydroxynitriles. Deprotonating acyclic, and cyclic, beta-hydroxynitriles with excess MeMgCl smoothly generates dianion intermediates that eject MgO with concurrent formation of alpha,beta-unsaturated nitriles. Alternatively, sequential addition of lithioacetonitrile and MgBr(2) to aldehydes and ketones generates magnesium

  通过从β-羟基腈中除去MgO，可以轻松合成α，β-不饱和腈。用过量的MeMgCl对无环和环状的β-羟基腈进行去质子处理可平稳生成二价阴离子中间体，该中间体可排出MgO，同时形成α，β-不饱和腈。或者，将硫代乙腈和MgBr（2）依次添加到醛和酮中，可在原位生成烷氧基镁，可在添加MeMgCl后消除MgO。MeMgCl诱导的MgO消除可从受阻的酮中平稳生成α，β-不饱和腈，否则这些酮难以合成。
• Chiral β- and γ-aminoalcohols derived from (+)-camphor and (−)-fenchone as catalysts for the enantioselective addition of diethylzinc to benzaldehyde
  作者：Vladimir Dimitrov、Georgi Dobrikov、Miroslav Genov

  DOI：10.1016/s0957-4166(01)00221-x

  日期：2001.6

  The addition of Me3SiCN and LICH2CN to (+)-camphor and (-)-fenchone. respectively, followed by reduction leads to chiral beta- and gamma -aminoalcohols. The enantioselectivities realized using these aminoalcohols as ligands in the addition of Et2Zn to benzaldehyde were lower than those obtained using the corresponding delta -aminoalcohols. (C) 2001 Elsevier Science Ltd. All rights reserved.