2-氯-5-(氯甲基)吡啶-3-甲腈 | 1360900-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 2-氯-5-(氯甲基)吡啶-3-甲腈
• 英文名称: 2-chloro-5-(chloromethyl)nicotinonitrile
• 英文别名: 2-Chloro-5-(chloromethyl)nicotinonitrile；2-chloro-5-(chloromethyl)pyridine-3-carbonitrile
• CAS: 1360900-22-6
• 化学式: C₇H₄Cl₂N₂
• mdl: MFCD24465532
• 分子量: 187.028
• InChiKey: NMRFKJBMCZWYTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  36.7
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  1-异丙基哌嗪 、 2-氯-5-(氯甲基)吡啶-3-甲腈 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Flexible and Scalable Route to HDAc Inhibitors Containing an Unusual Trisubstituted Pyridine Core

  摘要：

  A scalable route to histone deacetylase inhibitors containing an unusual 2-aryl-3-cyano-5-aminomethylpyridine core has been developed which has the flexibility to deliver a range of compounds on at least a multigram scale. The key step involves a novel Mannich reaction using 3-dimethylaminoacrolein, formaldehyde, and a secondary amine to yield a 2-(alkylaminomethyl)-3-dimethylaminoacrolein. Tuning of this reaction in process development was fundamental to the success of the approach in terms of flexibility and operability on scale-up. This new methodology will also enable access an underutilised family of 3,5-disubstituted pyrid-2-ones and 2,3,5-trisubstituted pyridines.

  DOI：

  10.1021/op300021m
• 作为产物：
  描述：

  5-(morpholin-4-ylmethyl)-2-oxo-1,2-dihydropyridine-3-carbonitrile 在 氯甲酸乙酯 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 60.0h， 生成 2-氯-5-(氯甲基)吡啶-3-甲腈
  参考文献：
  名称：

  Flexible and Scalable Route to HDAc Inhibitors Containing an Unusual Trisubstituted Pyridine Core

  摘要：

  A scalable route to histone deacetylase inhibitors containing an unusual 2-aryl-3-cyano-5-aminomethylpyridine core has been developed which has the flexibility to deliver a range of compounds on at least a multigram scale. The key step involves a novel Mannich reaction using 3-dimethylaminoacrolein, formaldehyde, and a secondary amine to yield a 2-(alkylaminomethyl)-3-dimethylaminoacrolein. Tuning of this reaction in process development was fundamental to the success of the approach in terms of flexibility and operability on scale-up. This new methodology will also enable access an underutilised family of 3,5-disubstituted pyrid-2-ones and 2,3,5-trisubstituted pyridines.

  DOI：

  10.1021/op300021m