4-[(R)-Hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile | 918413-82-8

• 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: 4-[(R)-Hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile
• 英文别名: 4-[(R)-Hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzonitrile；4-[(R)-hydroxy-(3-methylimidazol-4-yl)methyl]benzonitrile
• CAS: 918413-82-8
• 化学式: C₁₂H₁₁N₃O
• 分子量: 213.239
• InChiKey: IECJLKDQPXYAOB-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  61.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-methyl-3H-imidazol-4-yl magnesium chloride 、 4-氰基苯甲醛 在 Dimethylzinc 、 (1R)-反-N,N′-1,2-环己二基双(1,1,1-三氟甲磺酰胺) 作用下， 以 二氯甲烷 为溶剂， 生成 4-[(R)-Hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile 、 4-[(S)-Hydroxy-(3-methyl-3H-imidazol-4-yl)-methyl]-benzonitrile
  参考文献：
  名称：

  Enantioselective synthesis of the farnesyltransferase inhibitor, A-345665.0

  摘要：

  The stereoselective synthesis of A-345665.0 1, a novel farnesyl transferase inhibitor, is described. The key step involves a stereoselective addition of an imidazolyl Grignard reagent to aldehyde 8 in the presence of an external chiral auxiliary. Crystallization of the product as the dimeric zinc complex 12 facilitates the isolation of product in > 98:2 er. The biaryl linkage is formed by the use of a Suzuki coupling, employing boronic acid 4 prepared by the directed ortho-lithiation of benzonitrile 6. The overall yield for the six step sequence is 21%. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.10.008

文献信息

• Enantioselective synthesis of the farnesyltransferase inhibitor, A-345665.0
  作者：Michael J. Rozema、Michael Fickes、Maureen McLaughlin、Bridget Rohde、Todd McDermott

  DOI：10.1016/j.tetlet.2006.10.008

  日期：2006.12

  The stereoselective synthesis of A-345665.0 1, a novel farnesyl transferase inhibitor, is described. The key step involves a stereoselective addition of an imidazolyl Grignard reagent to aldehyde 8 in the presence of an external chiral auxiliary. Crystallization of the product as the dimeric zinc complex 12 facilitates the isolation of product in > 98:2 er. The biaryl linkage is formed by the use of a Suzuki coupling, employing boronic acid 4 prepared by the directed ortho-lithiation of benzonitrile 6. The overall yield for the six step sequence is 21%. (c) 2006 Elsevier Ltd. All rights reserved.