(S)-diethyl 3-(2-(hydroxymethyl)pyrrolidin-1-yl)prop-1-en-2-ylphosphonate | 1235976-67-6

• 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: (S)-diethyl 3-(2-(hydroxymethyl)pyrrolidin-1-yl)prop-1-en-2-ylphosphonate
• 英文别名: [(2S)-1-(2-diethoxyphosphorylprop-2-enyl)pyrrolidin-2-yl]methanol
• CAS: 1235976-67-6
• 化学式: C₁₂H₂₄NO₄P
• 分子量: 277.301
• InChiKey: YOVAXXAEPLBWKW-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(diethoxyphosphoryl)allyl acetate 、 L-脯氨醇 以 四氢呋喃 为溶剂， 反应 24.0h， 以82%的产率得到(S)-diethyl 3-(2-(hydroxymethyl)pyrrolidin-1-yl)prop-1-en-2-ylphosphonate
  参考文献：
  名称：

  Synthesis of β-aminovinylphosphonates by organocatalytic nucleophilic displacement of acetate with amines

  摘要：

  The synthesis of diethyl beta-aminovinylphosphonates 2 from acetoxy phosphonate 1 is described. The reaction entails an organocatalyzed substitution of the acetoxy group by primary or secondary amines. The use of a catalytic amount of DABCO is necessary if the amine is not nucleophilic enough, otherwise a strong nucleophilic amine can react without organocatalyst. The reaction led to a series of functionalized title compounds in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.05.050

文献信息

• Synthesis of β-aminovinylphosphonates by organocatalytic nucleophilic displacement of acetate with amines
  作者：Cécile Garzon、Mireille Attolini、Michel Maffei

  DOI：10.1016/j.tetlet.2010.05.050

  日期：2010.7

  The synthesis of diethyl beta-aminovinylphosphonates 2 from acetoxy phosphonate 1 is described. The reaction entails an organocatalyzed substitution of the acetoxy group by primary or secondary amines. The use of a catalytic amount of DABCO is necessary if the amine is not nucleophilic enough, otherwise a strong nucleophilic amine can react without organocatalyst. The reaction led to a series of functionalized title compounds in good to excellent yields. (C) 2010 Elsevier Ltd. All rights reserved.
• Organocatalyzed synthesis of functionalized vinylphosphonates in water
  作者：Adeline Seingeot、Yolande Charmasson、Mireille Attolini、Michel Maffei

  DOI：10.1002/hc.21352

  日期：2017.1

  AbstractThe reaction between diethyl(α‐acetoxymethyl)vinylphosphonate 1 and nitrogen‐ or sulfur‐based nucleophiles occurs easily at room temperature in water as a solvent in the presence of 1,4‐diazabicyclo [2.2.1]octane (DABCO) as an organocatalyst. This simple procedure enables the synthesis of nitrogen‐ and sulfur substituted vinylphosphonates, and also allows a convenient use of water‐soluble salts as nucleophiles.