(1,1-difluoro-4-phenylpenta-2,3-dienyl)phosphonic acid diethyl ester

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1,1-difluoro-4-phenylpenta-2,3-dienyl)phosphonic acid diethyl ester
• 化学式: C₁₅H₁₉F₂O₃P
• 分子量: 316.285
• InChiKey: YXXUJENAEUPCCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  41.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1,1-difluoro-4-phenylpenta-2,3-dienyl)phosphonic acid diethyl ester 在 碘 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以64%的产率得到2-ethoxy-3,3-difluoro-5-iodo-6-methyl-6-phenyl-3,6-dihydro[1,2]oxaphosphinine 2-oxide
  参考文献：
  名称：

  First iodocyclization of β-allenic phosphonates: a novel synthesis of α-difluoromethylenephostones

  摘要：

  Six-membered alpha-difluoromethylenephostones were prepared in moderate to good yields with high regioselectivities under mild conditions from the iodocyclization reaction of diethyl beta-allenic alpha,alpha-difluorophosphonates using I-2 or ICl as the electrophile. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.096
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 、 2-phenyl-3-butyn-2-yl acetate 在 锌 、 copper(I) bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以66%的产率得到(1,1-difluoro-4-phenylpenta-2,3-dienyl)phosphonic acid diethyl ester
  参考文献：
  名称：

  A facile method to construct cyclic α,α-difluoromethylenephosphonate—A novel cyclic phosphate mimic

  摘要：

  A facile and efficient synthesis of cyclic alpha,alpha-difluoromethylenephosphonates by halogen-induced intramolecular cyclization of beta-allenic alpha,alpha-difluoromethylenephosphonates is described. The protocol gives multi-substituted six-membered phosphonates with high regioselectivity, providing a new entry to the cyclic phosphate mimics which is still an unexplored but promising area. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2011.02.014

文献信息

• First iodocyclization of β-allenic phosphonates: a novel synthesis of α-difluoromethylenephostones
  作者：Yun Lin、Jin-Tao Liu

  DOI：10.1016/j.tetlet.2006.06.096

  日期：2006.8

  Six-membered alpha-difluoromethylenephostones were prepared in moderate to good yields with high regioselectivities under mild conditions from the iodocyclization reaction of diethyl beta-allenic alpha,alpha-difluorophosphonates using I-2 or ICl as the electrophile. (c) 2006 Elsevier Ltd. All rights reserved.
• A facile method to construct cyclic α,α-difluoromethylenephosphonate—A novel cyclic phosphate mimic
  作者：Yun Lin、Jin-Tao Liu

  DOI：10.1016/j.jfluchem.2011.02.014

  日期：2011.5

  A facile and efficient synthesis of cyclic alpha,alpha-difluoromethylenephosphonates by halogen-induced intramolecular cyclization of beta-allenic alpha,alpha-difluoromethylenephosphonates is described. The protocol gives multi-substituted six-membered phosphonates with high regioselectivity, providing a new entry to the cyclic phosphate mimics which is still an unexplored but promising area. (C) 2011 Elsevier B.V. All rights reserved.