(1-Fluoro-1-methyl-3-phenyl-prop-2-ynyl)-phosphonic acid diethyl ester | 178943-97-0

• 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: (1-Fluoro-1-methyl-3-phenyl-prop-2-ynyl)-phosphonic acid diethyl ester
• 英文别名: (3-Diethoxyphosphoryl-3-fluorobut-1-ynyl)benzene
• CAS: 178943-97-0
• 化学式: C₁₄H₁₈FO₃P
• 分子量: 284.267
• InChiKey: HEYDNOROTRIZEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1-Fluoro-1-methyl-3-phenyl-prop-2-ynyl)-phosphonic acid diethyl ester 在 喹啉 、 Pd-BaSO₄ 氢气 作用下， 以 吡啶 为溶剂， 反应 48.0h， 以99%的产率得到((Z)-1-Fluoro-1-methyl-3-phenyl-allyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Synthesis of α-fluoro-β, γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate

  摘要：

  The efficient preparation of alpha-fluoro-beta,gamma-alkenylphosphonate 3, via catalytic hydrogenation of (alpha-fluoropropargyl)phosphonate ester 1, is described. Conjugated fluoroenynes 4 have been synthesized using a modified Horner Wadsworth Emmons (HWE) olefination of aldehydes or ketones and 1 in relatively good yields. Yields were lowered because of the formation of alpha-fluoro-gamma-hydroxyallenylphosphonate 5 during the reaction. The nature of the counterion was very important in the outcome of the HWE reaction; better yields of fluoroenynes were obtained when a potassium base was used instead of a lithium base. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01017-5
• 作为产物：
  描述：

  4-苯基-3-丁炔-2-酮 在 potassium fluoride 、 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (1-Fluoro-1-methyl-3-phenyl-prop-2-ynyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  Efficient Syntheses of (α-Fluoropropargyl)phosphonate Esters

  摘要：

  DOI：

  10.1021/jo9602027

文献信息

• Efficient Syntheses of (α-Fluoropropargyl)phosphonate Esters
  作者：Farid Benayoud、Daniel J. deMendonca、Cheryl A. Digits、George A. Moniz、Tanya C. Sanders、Gerald B. Hammond

  DOI：10.1021/jo9602027

  日期：1996.1.1
• Synthesis of α-fluoro-β, γ-alkenylphosphonates and conjugated fluoroenynes from a common intermediate (α-fluoropropargyl) phosphonate
  作者：Farid Benayoud、Ling Chen、George A. Moniz、Antonio J. Zapata、Gerald B. Hammond

  DOI：10.1016/s0040-4020(98)01017-5

  日期：1998.12

  The efficient preparation of alpha-fluoro-beta,gamma-alkenylphosphonate 3, via catalytic hydrogenation of (alpha-fluoropropargyl)phosphonate ester 1, is described. Conjugated fluoroenynes 4 have been synthesized using a modified Horner Wadsworth Emmons (HWE) olefination of aldehydes or ketones and 1 in relatively good yields. Yields were lowered because of the formation of alpha-fluoro-gamma-hydroxyallenylphosphonate 5 during the reaction. The nature of the counterion was very important in the outcome of the HWE reaction; better yields of fluoroenynes were obtained when a potassium base was used instead of a lithium base. (C) 1998 Elsevier Science Ltd. All rights reserved.