3-(4-(hydroxymethyl)benzoyl)benzonitrile | 1345046-82-3

• 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: 3-(4-(hydroxymethyl)benzoyl)benzonitrile
• 英文别名: 3-[4-(Hydroxymethyl)benzoyl]benzonitrile；3-[4-(hydroxymethyl)benzoyl]benzonitrile
• CAS: 1345046-82-3
• 化学式: C₁₅H₁₁NO₂
• 分子量: 237.258
• InChiKey: ULPOAQKBEUJHHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-(hydroxymethyl)benzoyl)benzonitrile 在 glucose dehydrogenase 、 葡萄糖 、 ketoreductase 115 、 NADPH cofactor 作用下， 以 二甲基亚砜 为溶剂， 以98%的产率得到(S)-3-(hydroxy(4-(hydroxymethyl)phenyl)methyl)benzonitrile
  参考文献：
  名称：

  Diarylketone Ketoreductase Screen and Synthesis Demonstration to Access mGlu2 Receptor Potentiators

  摘要：

  This communication describes proof of concept for an enantioselective enzyme-based synthesis of diarylmethanol (S)-1 to access mGlu2 receptor potentiators. A ketoreductase (KRED) screen was applied to benzophenone 8 to afford chiral diarylmethanol (S)-9, which is a useful intermediate for the preparation of chiral diarylmethanol (S)-1. In addition, a more practical synthesis of benzophenone 8 was demonstrated utilizing Friedel Crafts acylation and radical bromination chemistry.

  DOI：

  10.1021/op2002479
• 作为产物：
  描述：

  3-(4-methylbenzoyl)benzonitrile 在 偶氮二异丁腈 、 水 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 3-(4-(hydroxymethyl)benzoyl)benzonitrile
  参考文献：
  名称：

  Diarylketone Ketoreductase Screen and Synthesis Demonstration to Access mGlu2 Receptor Potentiators

  摘要：

  This communication describes proof of concept for an enantioselective enzyme-based synthesis of diarylmethanol (S)-1 to access mGlu2 receptor potentiators. A ketoreductase (KRED) screen was applied to benzophenone 8 to afford chiral diarylmethanol (S)-9, which is a useful intermediate for the preparation of chiral diarylmethanol (S)-1. In addition, a more practical synthesis of benzophenone 8 was demonstrated utilizing Friedel Crafts acylation and radical bromination chemistry.

  DOI：

  10.1021/op2002479