(1-Fluoro-but-2-ynyl)-phosphonic acid diethyl ester | 150972-87-5

• 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-but-2-ynyl)-phosphonic acid diethyl ester
• 英文别名: Phosphonic acid, (1-fluoro-2-butynyl)-, diethyl ester；1-diethoxyphosphoryl-1-fluorobut-2-yne
• CAS: 150972-87-5
• 化学式: C₈H₁₄FO₃P
• 分子量: 208.17
• InChiKey: RKBSXDLVZYGJIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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-but-2-ynyl)-phosphonic acid diethyl ester 在 aluminum oxide 、 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以89%的产率得到((Z)-1-Fluoro-but-2-enyl)-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：

  (1-Hydroxy-but-2-ynyl)-phosphonic acid diethyl ester 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以85%的产率得到(1-Fluoro-but-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
• A regiospecific fluorination strategy: synthesis of .alpha.-fluoropropargyl- and .alpha.-fluoroallylphosphonate esters
  作者：Tanya C. Sanders、Gerald B. Hammond

  DOI：10.1021/jo00073a012

  日期：1993.10

  A common approach to the synthesis of 6 and 7 involving regiospecific fluorination of the hydroxy group in beta,gamma-unsaturated alpha-hydroxy phosphonates is described.
• 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.
• The crystal structure of 2-fluoro-1-(p-methoxyphenyl)-1-penten-3-yne, a fluorinated vinylacetylene prepared via Horner-Wadsworth-Emmons condensation
  作者：Tanya C. Sanders、James A. Golen、Paul G. Williard、Gerald B. Hammond

  DOI：10.1016/s0022-1139(97)00064-x

  日期：1997.10

  Horner-Wadsworth-Emmons condensation of (alpha-fluoropropargyl) phosphonate ester 3 and p-anisaldehyde provides a new method for the synthesis of monofluoro-conjugated enynes. Spontaneous crystallization of 4 yielded the Z isomer of 2-fluoro-1-(p-methoxyphenyl)-1-petnen-3-yne. A comparison of bond angles and distances between 4 and vinylacetylene showed shorter bond distances along the enyne system in 4. (C) 1997 Elsevier Science S.A.