(2-氰基-5-甲酰基苯基)硼酸 | 918413-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (2-氰基-5-甲酰基苯基)硼酸
• 英文名称: (2-CYANO-5-FORMYLPHENYL)BORONIC ACID
• CAS: 918413-80-6
• 化学式: C₈H₆BNO₃
• mdl: MFCD10697411
• 分子量: 174.952
• InChiKey: BVYVLTMIKIKMCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.13
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-氰基-5-甲酰基苯基)硼酸 在 palladium diacetate 、 potassium fluoride 、 2-(二环己基膦基)联苯 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 4-[(R)-(4-cyanophenyl)methoxy-(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 硼酸三异丙酯 、 2,2,6,6-tetramethylpiperidinyl-lithium 作用下， 以70%的产率得到(2-氰基-5-甲酰基苯基)硼酸
  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