1-(7-Chloro-3-methyl-furo[2,3-c]pyridin-5-yl)-ethanone | 215584-04-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡啶类
• 英文名称: 1-(7-Chloro-3-methyl-furo[2,3-c]pyridin-5-yl)-ethanone
• 英文别名: 1-(7-Chloro-3-methylfuro[2,3-c]pyridin-5-yl)ethanone
• CAS: 215584-04-6
• 化学式: C₁₀H₈ClNO₂
• 分子量: 209.632
• InChiKey: DDEUKYUNMVKMIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  43.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(7-Chloro-3-methyl-furo[2,3-c]pyridin-5-yl)-ethanone 在 (-)-diisopinocamphenylborane chloride 作用下， 以 四氢呋喃 为溶剂， 以94%的产率得到(S)-1-(7-Chloro-3-methyl-furo[2,3-c]pyridin-5-yl)-ethanol
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359
• 作为产物：
  描述：

  2-chloro-3-hydroxy-6-(1-hydroxyethyl)-pyridine 在 palladium diacetate 、 草酰氯 、 四丁基氯化铵 、 碘 、 sodium formate 、 sodium hydride 、 sodium carbonate 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.07h， 生成 1-(7-Chloro-3-methyl-furo[2,3-c]pyridin-5-yl)-ethanone
  参考文献：
  名称：

  Stereoselective Synthesis of Furo[2,3-c]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors

  摘要：

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.

  DOI：

  10.1021/jo9810359

文献信息

• Process for producing optically active pyridineethanol derivatives
  申请人：Kaneka Corporation

  公开号：US20040043460A1

  公开（公告）日：2004-03-04

  The present invention relates to a method of producing an optically active pyridineethanol derivative. More particularly, it relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing an enzyme or enzyme source to act on polycyclic acetylpyridine derivatives. The present invention also relates to a novel enzyme which can be used in the production method mentioned above, a DNA coding for said enzyme, a recombinant vector having said DNA, and a transformant having said recombinant vector. The invention further relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing the above novel enzyme or the above transformant to act on optically inactive polycyclic pyridineethanol derivatives.

  本发明涉及一种制备光学活性吡啶乙醇衍生物的方法。更具体地说，它涉及通过使酶或酶源作用于多环乙酰吡啶衍生物来制备光学活性多环吡啶乙醇衍生物的方法。本发明还涉及一种新的酶，可用于上述制备方法，以及编码该酶的DNA，具有该DNA的重组载体和具有该重组载体的转化体。本发明还涉及一种通过使上述新酶或上述转化体作用于光学不活性多环吡啶乙醇衍生物来制备光学活性多环吡啶乙醇衍生物的方法。
• PROCESS FOR PRODUCING OPTICALLY ACTIVE PYRIDINEETHANOL DERIVATIVES
  申请人：KANEKA CORPORATION

  公开号：EP1116795A1

  公开（公告）日：2001-07-18

  The present invention relates to a method of producing an optically active pyridineethanol derivative. More particularly, it relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing an enzyme or enzyme source to act on polycyclic acetylpyridine derivatives. The present invention also relates to a novel enzyme which can be used in the production method mentioned above, a DNA coding for said enzyme, a recombinant vector having said DNA, and a transformant having said recombinant vector. The invention further relates to a method of producing an optically active polycyclic pyridineethanol derivative by causing the above novel enzyme or the above transformant to act on optically inactive polycyclic pyridineethanol derivatives.

  本发明涉及一种生产光学活性吡啶乙醇衍生物的方法。更具体地说，它涉及一种通过使酶或酶源作用于多环乙酰基吡啶衍生物来生产光学活性多环吡啶乙醇衍生物的方法。 本发明还涉及一种可用于上述生产方法的新型酶、编码所述酶的 DNA、具有所述 DNA 的重组载体以及具有所述重组载体的转化体。 本发明还涉及一种生产光学活性多环吡啶乙醇衍生物的方法，其方法是使上述新型酶或上述转化体作用于光学无活性的多环吡啶乙醇衍生物。
• US7329518B2
  申请人：——

  公开号：US7329518B2

  公开（公告）日：2008-02-12
• Stereoselective Synthesis of Furo[2,3-<i>c</i>]pyridine Pyrimidine Thioethers, A New Class of Potent HIV-1 Non-nucleoside Reverse Transcriptase Inhibitors
  作者：Donn G. Wishka、David R. Graber、Eric P. Seest、Lester A. Dolak、Fusen Han、William Watt、Joel Morris

  DOI：10.1021/jo9810359

  日期：1998.10.1

  An efficient stereoselective total synthesis of the furo[2,3-c]pyridine thiopyrimidine HIV-1 reverse transcriptase inhibitors, PNU-142721 and PNU-109886, has been developed. A convergent approach was utilized, providing direct access to the desired (S)-configuration of the molecule by making use of the alkylation of 4-amino-6-chloro-2-thiopyrimidine with the appropriate (R)-1-chloroethyl furo[2,3-c]pyridine intermediates. The successful preparation makes use of an efficient enzymatic kinetic resolution of the key 1-hydroxyethyl furo[2,3-c]pyridine intermediates to establish stereochemical control of the respective stereogenic centers. In addition, a workable asymmetric reduction strategy was developed for the synthesis of PNU-109886. Prudent reagent selection for the chlorination required for the final coupling reactions allowed for maintenance of the stereochemical integrity of the target compounds. Structural assignment of the absolute configuration of PNU-142721 and PNU-109886 as the (S)-enantiomer was confirmed by X-ray crystallographic analysis.