isopropyl 2-fluoro-2-diethylphosphonoacetate | 190668-15-6

• 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: isopropyl 2-fluoro-2-diethylphosphonoacetate
• 英文别名: Propan-2-yl 2-diethoxyphosphoryl-2-fluoroacetate
• CAS: 190668-15-6
• 化学式: C₉H₁₈FO₅P
• 分子量: 256.211
• InChiKey: BMILDMDSSKPIMI-UHFFFAOYSA-N

物化性质

• 沸点：
  300.4±32.0 °C(Predicted)
• 密度：
  1.145±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-t-butyl-1,3-dioxan-5-one 、 isopropyl 2-fluoro-2-diethylphosphonoacetate 在 N-乙基哌啶 、 tin(II) trifluoromethanesulfonate 、 (S)-(-)-1-甲基-2-(1-哌啶基甲基)吡咯烷 作用下， 以 二氯甲烷 为溶剂， 反应 41.5h， 生成 (2-tert-Butyl-[1,3]dioxan-5-ylidene)-fluoro-acetic acid isopropyl ester 、 (2-tert-Butyl-[1,3]dioxan-5-ylidene)-fluoro-acetic acid isopropyl ester
  参考文献：
  名称：

  Enantioselective Horner–Wadsworth–Emmons reaction for the asymmetric synthesis of α-fluoro-α,β-unsaturated esters

  摘要：

  The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-dietliylphosphonoacetates with sigma-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO2CF3)(2) and N-ethylpiperidine in the presence of an external chiral ligand, (S)-(-)-1-methyl-2-(1-piperidinomethyl)pyrrolidine. A chiral alpha-fluoro-alpha,beta-unsaturated ester was obtained in up to 80% ce. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02135-9
• 作为产物：
  描述：

  二乙基[二溴(氟)甲基]膦酸酯 、 氯甲酸异丙酯 在 正丁基锂 、 三甲基氯硅烷 、 乙醇 作用下， 生成 isopropyl 2-fluoro-2-diethylphosphonoacetate
  参考文献：
  名称：

  New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid

  摘要：

  Diethyl 1-fluoromethylphosphonocarboxylic esters 4, bearing a variety of ester groups (alkyl, aryl), have been conveniently prepared in a one-pot process, by reaction of chloroformates with 1-lithio-1-fluoro-1-(trimethylsilyl)methylphosphonate 2 derived from 1,1-dibromo-1-fluoromethylphosphonate 1. The overall yields generally range from 80 to 91%. Reaction of 2 with CO2 leads to a novel efficient synthesis of diethyl 1-fluoromethylphosphonocarboxylic acid 7 in 86% yield. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00312-8

文献信息

• New routes to diethyl 1-fluoromethylphosphonocarboxylates and diethyl 1-fluoromethylphosphonocarboxylic acid
  作者：Rachel Waschbüsch、John Carran、Philippe Savignac

  DOI：10.1016/s0040-4020(97)00312-8

  日期：1997.5

  Diethyl 1-fluoromethylphosphonocarboxylic esters 4, bearing a variety of ester groups (alkyl, aryl), have been conveniently prepared in a one-pot process, by reaction of chloroformates with 1-lithio-1-fluoro-1-(trimethylsilyl)methylphosphonate 2 derived from 1,1-dibromo-1-fluoromethylphosphonate 1. The overall yields generally range from 80 to 91%. Reaction of 2 with CO2 leads to a novel efficient synthesis of diethyl 1-fluoromethylphosphonocarboxylic acid 7 in 86% yield. (C) 1997 Elsevier Science Ltd.
• Enantioselective Horner–Wadsworth–Emmons reaction for the asymmetric synthesis of α-fluoro-α,β-unsaturated esters
  作者：Shigeki Sano、Kenji Yokoyama、Rie Teranishi、Motoo Shiro、Yoshimitsu Nagao

  DOI：10.1016/s0040-4039(01)02135-9

  日期：2002.1

  The enantioselective Horner-Wadsworth-Emmons reaction of 2-fluoro-2-dietliylphosphonoacetates with sigma-symmetric prochiral 2-substituted-1,3-dioxan-5-ones and 4-substituted-cyclohexanones was investigated by employing Sn(OSO2CF3)(2) and N-ethylpiperidine in the presence of an external chiral ligand, (S)-(-)-1-methyl-2-(1-piperidinomethyl)pyrrolidine. A chiral alpha-fluoro-alpha,beta-unsaturated ester was obtained in up to 80% ce. (C) 2002 Elsevier Science Ltd. All rights reserved.