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

文献信息

• Flexible and Scalable Route to HDAc Inhibitors Containing an Unusual Trisubstituted Pyridine Core
  作者：Mark A. Graham、Steven A. Raw、David M. Andrews、Catherine J. Good、Zbigniew S. Matusiak、Mark Maybury、Elaine S. E. Stokes、Andrew T. Turner

  DOI：10.1021/op300021m

  日期：2012.7.20

  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.