diisopropyl (3-hydroxyprop-1-yn-1-yl)phosphonate | 34199-83-2

• 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: diisopropyl (3-hydroxyprop-1-yn-1-yl)phosphonate
• 英文别名: 3-Di(propan-2-yloxy)phosphorylprop-2-yn-1-ol；3-di(propan-2-yloxy)phosphorylprop-2-yn-1-ol
• CAS: 34199-83-2
• 化学式: C₉H₁₇O₄P
• 分子量: 220.205
• InChiKey: SXXVEMSCCUHMIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diisopropyl (3-hydroxyprop-1-yn-1-yl)phosphonate 在 甲醇 、 水 、 silver nitrate 作用下， 反应 24.0h， 以80%的产率得到diisopropyl (3-hydroxy-2-oxopropyl)phosphonate
  参考文献：
  名称：

  Synthesis of β-ketophosphonates via AgNO3-catalyzed hydration of alkynylphosphonates: a rate-enhancement effect of methanol

  摘要：

  beta-Ketophosphonates were prepared via AgNO3-catalyzed hydration of alkynylphosphonates with a dramatic rate-enhancement effect of methanol. This benign aqueous-methanol method catalyzed by a low-(c)ost catalyst has simple, atom-economical procedure, and was used effectively with a wide range of substrates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.12.001
• 作为产物：
  描述：

  亚磷酸二异丙酯 、 2-丙炔-1-醇 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 以99%的产率得到diisopropyl (3-hydroxyprop-1-yn-1-yl)phosphonate
  参考文献：
  名称：

  Cuproussiloxane as two self-assemblies, Cu₂₀O₂₀Si₁₀Me₁₀R₁₀ and Cu₂₄O₂₄Si₁₂Me₁₂R₁₂, with catalytic property

  摘要：

  制备并利用一种亚铜硅氧烷催化末端炔烃与 H-膦酸盐的有氧 C-P 偶联反应，生成炔膦酸盐。

  DOI：

  10.1039/d2dt01018f

文献信息

• Gao, Yuxing; Wang, Gang; Chen, Lu, Journal of the American Chemical Society, 2009, vol. 131, p. 7956 - 7957
  作者：Gao, Yuxing、Wang, Gang、Chen, Lu、Xu, Pengxiang、Zhao, Yufen、et al.

  DOI：——

  日期：——
• Palladium-Catalyzed Domino Addition and Cyclization of Arylboronic Acids with 3-Hydroxyprop-1-yn-1-yl Phosphonates Leading to 1,2-Oxaphospholenes
  作者：Ye Lv、Gaobo Hu、Dumei Ma、Liu Leo Liu、Yuxing Gao、Yufen Zhao

  DOI：10.1021/acs.joc.5b00999

  日期：2015.7.2

  A novel and efficient palladium-catalyzed domino addition-cyelization of a wide range of arylboronic acids with various 3-hydroxyprop-1-yn-1-yl phosphonates has been developed, affording a convenient and powerful tool for the preparation of valuable 1,2-oxaphospholenes with mild reaction conditions, broad substrate applicability, and good to excellent yields. Mechanistic studies revealed that the reaction might involve Michael addition and nucleophilic substitution.
• Synthesis of β-ketophosphonates via AgNO3-catalyzed hydration of alkynylphosphonates: a rate-enhancement effect of methanol
  作者：Jiannan Xiang、Niannian Yi、Ruijia Wang、Linghui Lu、Huaxu Zou、Yuan Pan、Weimin He

  DOI：10.1016/j.tet.2014.12.001

  日期：2015.1

  beta-Ketophosphonates were prepared via AgNO3-catalyzed hydration of alkynylphosphonates with a dramatic rate-enhancement effect of methanol. This benign aqueous-methanol method catalyzed by a low-(c)ost catalyst has simple, atom-economical procedure, and was used effectively with a wide range of substrates. (C) 2014 Elsevier Ltd. All rights reserved.
• Cuproussiloxane as two self-assemblies, Cu₂₀O₂₀Si₁₀Me₁₀R₁₀ and Cu₂₄O₂₄Si₁₂Me₁₂R₁₂, with catalytic property
  作者：Wenjun Jiang、Jinjin Wang、Yilin Chen、Zhikang Chen、Jiancheng Li、Liuyin Jiang、Yanbo Peng、Hongping Zhu

  DOI：10.1039/d2dt01018f

  日期：——

  A cuproussiloxane is prepared and utilized to catalyze the aerobic C–P coupling of terminal alkynes with H-phosphonates to alkynylphosphonates.

  制备并利用一种亚铜硅氧烷催化末端炔烃与 H-膦酸盐的有氧 C-P 偶联反应，生成炔膦酸盐。