diethyl (1-fluoro-1-(phenylsulfonyl)prop-2-yn-1-yl)phosphonate | 1428440-13-4

• 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: diethyl (1-fluoro-1-(phenylsulfonyl)prop-2-yn-1-yl)phosphonate
• 英文别名: (1-Diethoxyphosphoryl-1-fluoroprop-2-ynyl)sulfonylbenzene；(1-diethoxyphosphoryl-1-fluoroprop-2-ynyl)sulfonylbenzene
• CAS: 1428440-13-4
• 化学式: C₁₃H₁₆FO₅PS
• 分子量: 334.305
• InChiKey: MOIYXINJLFXQHY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯砜基甲基膦酸二乙酯 在 sodium hydride 、 (2S,4S,5R)-1-(anthracen-9-ylmethyl)-5-ethenyl-2-[(R)-(prop-2-en-1-yloxy)(quinolin-4-yl)methyl]-1-azabicyclo[2.2.2]octan-1-ium bromide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.0h， 生成 diethyl (1-fluoro-1-(phenylsulfonyl)prop-2-yn-1-yl)phosphonate
  参考文献：
  名称：

  Organocatalytic alkynylation of densely functionalized monofluorinated derivatives: C(sp3)–C(sp) coupling

  摘要：

  Organocatalytic alkynylation of nucleophilic fluorocarbons using hypervalent iodine compounds under cinchona-based catalysis, namely using O-allyl N-anthracenyl cinchona alkaloid derivative II, is described. The reaction gives the final fluoro-propargyl compounds in good to excellent yields (up to 91%) and with moderate to low enantioselectivity (up to 61% ee). The reaction represents the first example of the use of hypervalent iodine compounds for the construction of fluorinated compounds and opens access to the preparation of biologically attractive compounds such as 1,2,3-triazoles. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.023

文献信息

• Organocatalytic alkynylation of densely functionalized monofluorinated derivatives: C(sp3)–C(sp) coupling
  作者：Martin Kamlar、Piotr Putaj、Jan Veselý

  DOI：10.1016/j.tetlet.2013.02.023

  日期：2013.4

  Organocatalytic alkynylation of nucleophilic fluorocarbons using hypervalent iodine compounds under cinchona-based catalysis, namely using O-allyl N-anthracenyl cinchona alkaloid derivative II, is described. The reaction gives the final fluoro-propargyl compounds in good to excellent yields (up to 91%) and with moderate to low enantioselectivity (up to 61% ee). The reaction represents the first example of the use of hypervalent iodine compounds for the construction of fluorinated compounds and opens access to the preparation of biologically attractive compounds such as 1,2,3-triazoles. (c) 2013 Elsevier Ltd. All rights reserved.