diethyl 2-hydroxy-2-(2'-pyridyl)ethanephosphonate | 438245-57-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: diethyl 2-hydroxy-2-(2'-pyridyl)ethanephosphonate
• 英文别名: 2-Diethoxyphosphoryl-1-pyridin-2-ylethanol
• CAS: 438245-57-9
• 化学式: C₁₁H₁₈NO₄P
• 分子量: 259.242
• InChiKey: RECQYQSIPJNMQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  68.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸乙烯酯 、 diethyl 2-hydroxy-2-(2'-pyridyl)ethanephosphonate 在 lipase from Pseudomonas aeruginosa (Toyobo Co) 作用下， 以 异丙醚 为溶剂， 反应 194.0h， 生成 diethyl (+)-(R)-2-hydroxy-2-(2'-pyridyl)ethanephosphonate 、 diethyl (S)-2-hydroxy-2-(2'-pyridyl)ethanephosphonate 、 diethyl (R)-2-acetoxy-2-(2'-pyridyl)ethanephosphonate 、 diethyl (S)-2-acetoxy-2-(2'-pyridyl)ethanephosphonate
  参考文献：
  名称：

  Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates

  摘要：

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00567-5
• 作为产物：
  描述：

  甲基膦酸二乙酯 在 sodium tetrahydroborate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 diethyl 2-hydroxy-2-(2'-pyridyl)ethanephosphonate
  参考文献：
  名称：

  Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates

  摘要：

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00567-5

文献信息

• Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
  作者：Remigiusz Żurawiński、Kaoru Nakamura、Józef Drabowicz、Piotr Kiełbasiński、Marian Mikołajczyk

  DOI：10.1016/s0957-4166(01)00567-5

  日期：2001.12

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.