(+/-)-4-chloro-2-(1-hydroxybutyl)pyridine | 872036-39-0

• 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
• 英文名称: (+/-)-4-chloro-2-(1-hydroxybutyl)pyridine
• 英文别名: 1-(4-Chloropyridin-2-yl)butan-1-ol
• CAS: 872036-39-0
• 化学式: C₉H₁₂ClNO
• 分子量: 185.653
• InChiKey: YYDUQZWFRIYMII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-4-chloro-2-(1-hydroxybutyl)pyridine 在 Pseudomonas cepacia lipase C 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 62.0h， 生成 (S)-(-)-4-(N,N-dimethylamino)-2-(1-hydroxybutyl)pyridine
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives

  摘要：

  Chiral 4-(N,N-dimethylamino)pyridine derivatives have been prepared through a chemoenzymatic synthesis where the enzymatic kinetic resolution of a family of 4-chloro-2-(1-hydroxyalkyl)pyridines is the key step for the formation of potentially important chiral catalysts. Pseudomonas cepacia lipase (PSL) showed excellent enantioselectivity in the acylation of the (R)-enantiomers (E > 200) using vinyl acetate as acylating agent and THF as solvent, obtaining products and substrates enantiomerically pure and with excellent yields. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.09.006
• 作为产物：
  描述：

  4-氯吡啶 N-氧化物 在 sodium tetrahydroborate 、 二甲氨基甲酰氯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 222.0h， 生成 (+/-)-4-chloro-2-(1-hydroxybutyl)pyridine
  参考文献：
  名称：

  Chemoenzymatic synthesis of chiral 4-(N,N-dimethylamino)pyridine derivatives

  摘要：

  Chiral 4-(N,N-dimethylamino)pyridine derivatives have been prepared through a chemoenzymatic synthesis where the enzymatic kinetic resolution of a family of 4-chloro-2-(1-hydroxyalkyl)pyridines is the key step for the formation of potentially important chiral catalysts. Pseudomonas cepacia lipase (PSL) showed excellent enantioselectivity in the acylation of the (R)-enantiomers (E > 200) using vinyl acetate as acylating agent and THF as solvent, obtaining products and substrates enantiomerically pure and with excellent yields. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2005.09.006

文献信息

• Enzymatic Preparation of Novel Aminoalkylpyridines using Lipases in Organic Solvents
  作者：Oliver Torre、Eduardo Busto、Vicente Gotor-Fernández、Vicente Gotor

  DOI：10.1002/adsc.200600634

  日期：2007.6.4

  enantiomerically pure 4-chloro(amino)pyridine derivatives has been synthesised through a chemoenzymatic approach, Candida antarctica lipase B (CAL-B) and Pseudomonas cepacia lipase (PSL) being found to be excellent biocatalysts for the preparation of new and interesting amines and amides in enantiomerically pure form through enzymatic aminolysis reactions. A study of the enzymatic reactivity of CAL-B and PSL

  已通过化学酶法合成了许多新颖的对映体纯的4-氯（氨基）吡啶衍生物，南极假丝酵母脂肪酶B（CAL-B）和假单胞菌洋葱脂肪酶（PSL）被认为是制备甲壳素的极好的生物催化剂。通过酶促氨解反应，以对映体纯净的形式出现新的有趣的胺和酰胺。CAL-B和PSL的酶反应性的研究已经在胺结构文库的拆分中进行了研究，以试图合理化由脂肪酶介导的酶动力学拆分所获得的实验结果。