diethyl (2-chloro-1-hydroxyethyl)phosphonate | 20641-57-0

• 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-chloro-1-hydroxyethyl)phosphonate
• 英文别名: diethyl 2-chloro-1-hydroxyethanephosphonate；(2-chloro-1-hydroxy-ethyl)-phosphonic acid diethyl ester；Diethyl-2-chloro-1-hydroxyethylphosphonat；2-Chloro-1-diethoxyphosphorylethanol
• CAS: 20641-57-0
• 化学式: C₆H₁₄ClO₄P
• 分子量: 216.602
• InChiKey: SDVQUOCECXDFCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (2-chloro-1-hydroxyethyl)phosphonate 在 氢氧化钾 作用下， 生成 (甲酰基甲基)磷酸二乙酯
  参考文献：
  名称：

  Synthesis of Dialkyl Epoxyethylphosphonates

  摘要：

  DOI：

  10.1055/s-1971-21664
• 作为产物：
  描述：

  epoxy-1,2 ethyl phosphonate de diethyle 在 四氯化钛 、 异氰酸苯酯 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以52%的产率得到diethyl (2-chloro-1-hydroxyethyl)phosphonate
  参考文献：
  名称：

  The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates

  摘要：

  A [3+2] cycloaddition of diethyl 1 2-oxiranephosphonate to aryl isocyanates catalyzed by lanthanide cations is described The reaction is highly regioselective and 5-substituted 2-oxazolidinone phosphonates are obtained with a regioselectivity greater than 95 5 with respect to the 4-substituted regioisomer and in up to 84% yield When 20 mol % of Pybox-Yb3+ is used as a catalyst enantiomerically enriched products are obtained in up to 75% ee depending on the reaction conditions and the nature of the isocyanate Low temperatures benefit asymmetric induction but have an adverse effect on the regioselectivity for para-substituted aryl isocyanates (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.028

文献信息

• Enzymatic synthesis of phosphocarnitine, phosphogabob and fosfomycinStudies on organophosphorus compounds. Part 128. For Part 127, see C. Yuan, C. Xu and Y. Zhang, Tetrahedron, 2003, 59, 6095.
  作者：Ke Wang、Yonghui Zhang、Chengye Yuan

  DOI：10.1039/b307638p

  日期：——

  Phosphocarnitine was conveniently obtained from easily available diethyl 3-chloro-2-oxopropanephosphonates, followed by subsequent reduction, Mucor miehei lipase (IM) mediated resolution, amination and dealkylation. Candida antarctica lipase B (CALB) served as an effective biocatalyst in the resolution of several 1- or 2- hydroxyalkanephosphonates. The chlorine atom in different positions on the molecules greatly affected their enantioselectivity. CALB also showed satisfactory enantioselectivity toward those molecules bearing an azido moiety. Both enantiomers of phosphogabob and fosfomycin were also prepared via CALB-mediated resolution as the key step.

  从易于获得的 3-氯-2-氧代丙烷膦酸二乙酯中方便地获得了磷卡尼汀，随后进行了还原、Mucor miehei 脂肪酶（IM）介导的解析、胺化和脱烷基化。白色念珠菌脂肪酶 B（CALB）是一种有效的生物催化剂，可用于多种 1-或 2-羟基烷基膦酸盐的分解。分子上不同位置的氯原子极大地影响了它们的对映选择性。CALB 对含有叠氮基的分子也表现出令人满意的对映选择性。磷霉素和磷霉素的两种对映体也都是通过 CALB 介导的解析作为关键步骤制备的。
• Nonenzymatic kinetic resolution of racemic α-hydroxyalkanephosphonates with chiral copper catalyst
  作者：Yosuke Demizu、Atsushi Moriyama、Osamu Onomura

  DOI：10.1016/j.tetlet.2009.07.003

  日期：2009.9

  Kinetic resolution of alpha-hydroxyalkanephosphonates was efficiently performed by benzoylation in the presence of copper(II) triflate and (R,R)-Ph-BOX as a catalyst with excellent s value of up to 286. (C) 2009 Elsevier Ltd. All rights reserved.
• US6583182B1
  申请人：——

  公开号：US6583182B1

  公开（公告）日：2003-06-24
• Synthesis of Dialkyl Epoxyethylphosphonates
  作者：Toshio AGAWA、Toshihiko KUBO、Yoshiki OHSHIRO

  DOI：10.1055/s-1971-21664

  日期：——
• The first enantioselective [3+2] cycloaddition of epoxides to arylisocyanates: asymmetric synthesis of chiral oxazolidinone phosphonates
  作者：Maria Teresa Barros、Ana Maria Faísca Phillips

  DOI：10.1016/j.tetasy.2010.10.028

  日期：2010.11

  A [3+2] cycloaddition of diethyl 1 2-oxiranephosphonate to aryl isocyanates catalyzed by lanthanide cations is described The reaction is highly regioselective and 5-substituted 2-oxazolidinone phosphonates are obtained with a regioselectivity greater than 95 5 with respect to the 4-substituted regioisomer and in up to 84% yield When 20 mol % of Pybox-Yb3+ is used as a catalyst enantiomerically enriched products are obtained in up to 75% ee depending on the reaction conditions and the nature of the isocyanate Low temperatures benefit asymmetric induction but have an adverse effect on the regioselectivity for para-substituted aryl isocyanates (C) 2010 Elsevier Ltd All rights reserved