4-formyl-2-(8-quinolinyl)benzonitrile | 565203-62-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 4-formyl-2-(8-quinolinyl)benzonitrile
• 英文别名: 4-Formyl-2-(quinolin-8-yl)benzonitrile；4-formyl-2-quinolin-8-ylbenzonitrile
• CAS: 565203-62-5
• 化学式: C₁₇H₁₀N₂O
• 分子量: 258.279
• InChiKey: VJRPBHKOFDBYPD-UHFFFAOYSA-N

物化性质

• 沸点：
  499.8±45.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 4-formyl-2-(8-quinolinyl)benzonitrile 在 正丁基锂 、 (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇 作用下， 生成 、 4-[(R)-hydroxy-(3-methylimidazol-4-yl)methyl]-2-quinolin-8-ylbenzonitrile
  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
• 作为产物：
  描述：

  4-(二乙氧基甲基)苯甲腈 在 palladium diacetate 、 potassium fluoride 、 硼酸三异丙酯 、 2,2,6,6-tetramethylpiperidinyl-lithium 、 2-(二环己基膦基)联苯 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 4-formyl-2-(8-quinolinyl)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

• Substituted phenyl farnesyltransferase inhibitors
  申请人：——

  公开号：US20020019527A1

  公开（公告）日：2002-02-14

  Compounds of formula (I) 1 or pharmaceutically acceptable salts thereof, inhibit farnesyltransferase. Methods for making the compounds, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds are disclosed.

  式(I)的化合物或其药学上可接受的盐，抑制法尼基转移酶。公开了制备这些化合物的方法，含有这些化合物的药物组合物，以及使用这些化合物进行治疗的方法。
• SUBSTITUTED PHENYL FARNESYLTRANSFERASE INHIBITORS
  申请人：Abbott Laboratories

  公开号：EP1276726A2

  公开（公告）日：2003-01-22
• [EN] SUBSTITUTED PHENYL FARNESYLTRANSFERASE INHIBITORS<br/>[FR] INHIBITEURS DE PHENYLE FARNESYLTRANSFERASE SUBSTITUES
  申请人：ABBOTT LAB

  公开号：WO2001081316A2

  公开（公告）日：2001-11-01

  Compounds of formula (I) or pharmaceutically acceptable salts thereof, inhibit farnesyltransferase. Methods for making the compounds, pharmaceutical compositions containing the compounds, and methods of treatment using the compounds are disclosed.
• 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.