膦酸,(3-羟基-1-丁烯基)-,二乙基酯,(E)- | 121044-46-0

• 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
• 中文名称: 膦酸,(3-羟基-1-丁烯基)-,二乙基酯,(E)-
• 英文名称: (E)-diethyl (3-hydroxybut-1en-1-yl)phosphonate
• 英文别名: diethyl (3-hydroxy-1-butenyl) phosphonate；(E)-4-diethoxyphosphorylbut-3-en-2-ol
• CAS: 121044-46-0
• 化学式: C₈H₁₇O₄P
• 分子量: 208.194
• InChiKey: XCYXLCYTXXNGBM-VOTSOKGWSA-N

物化性质

• 沸点：
  130-140 °C(Press: 1 Torr)
• 密度：
  1.1025 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  膦酸,(3-羟基-1-丁烯基)-,二乙基酯,(E)- 在 吡啶 、 氯化亚砜 作用下， 以 氯仿 为溶剂， 反应 0.25h， 以59%的产率得到(E)-diethyl-3-chloro-but-1-enylphosphonate
  参考文献：
  名称：

  Ryabov, B. V.; Ionin, B. I.; Petrov, A. A., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 859 - 871

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl (E)-crotylphosphonate 在 bis(trifluoroacetyl)peroxide 、 sodium ethanolate 、 sodium acetate 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.25h， 生成 膦酸,(3-羟基-1-丁烯基)-,二乙基酯,(E)-
  参考文献：
  名称：

  Ryabov, B. V.; Ionin, B. I.; Petrov, A. A., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 859 - 871

  摘要：

  DOI：

文献信息

• Enzymatic resolution of diethyl (3-hydroxy-1-butenyl) phosphonate
  作者：Mireille Attolini、Gilles Iacazio、Gilbert Peiffer、Michel Maffei

  DOI：10.1016/s0040-4039(02)02067-1

  日期：2002.11

  (3-hydroxy-1-butenyl) phosphonate 1 with different enzymes has been carried out, and allows the preparation of (S)-1 and (R)-diethyl (3-acetoxy-1-butenyl) phosphonate 2 with very high enantiomeric excess. The absolute conguration of 1 was determined by independent synthesis from (S)-ethyl lactate.

  （3-羟基-1-丁烯基）膦酸二乙酯1用不同的酶进行了酶促酯化反应，可以制备（S）-1和（R）-二乙基（3-乙酰氧基-1-丁烯基）膦酸酯。2具有很高的对映体过量。的绝对conguration 1是由来自（独立合成确定小号） -乳酸乙酯。
• New ω-ketovinyl phosphonates: inexpensive synthesis, isomerization studies and route for functionalized 1,3-butadienes
  作者：Gangaram Pallikonda、Swamy Maloth、Sathish Kumar Kurapati、M. Zubair Khalid Baig、Akhil Raj Kumar Saraswathi、Subhas Ghosal、Manab Chakravarty

  DOI：10.1016/j.tet.2015.06.064

  日期：2015.8

  A straightforward and inexpensive synthetic protocol to access new omega-ketovinyl phosphonates is established from the Lewis or Bronsted acid mediated reactions of alpha-hydroxy allylic phosphonates with aromatic 1,3-diketones. Predominantly, FeCl3 or FeCl3 center dot 6H(2)O has been preferred as easily available, inexpensive and efficient Lewis acid under solvent-free conditions. With experimental and theoretical support, we have demonstrated that some of the substituted open chain 1,3-diketones may exist predominantly in the keto form. Mild base mediated isomerization reactions for omega-ketovinyl phosphonates were carried out to generate corresponding allylic phosphonates. Utility of one of the allylic phosphonates in Horner-Wadsworth-Emmons (HWE) reactions facilitated access to variety of densely substituted 1,3-butadienes attached with 1,3-diketone functionality at the terminal carbon. (C) 2015 Elsevier Ltd. All rights reserved.
• RYABOV, B. V.;IONIN, B. I.;PETROV, A. A., ZH. OBSHCH. XIMII, 58,(1988) N 5, 969-983
  作者：RYABOV, B. V.、IONIN, B. I.、PETROV, A. A.

  DOI：——

  日期：——
• Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs
  作者：Sunghee Son、Gregory C. Fu

  DOI：10.1021/ja800103z

  日期：2008.3.1

  Complementing previous advances in allylation chemistry, an effective nickel/Pybox catalyst for regioselective asymmetric Negishi cross-couplings of racemic secondary allylic chlorides with readily available organozinc halides has been developed. The method has been applied in two key steps of a formal total synthesis of fluvirucinine A(1).
• Ryabov, B. V.; Ionin, B. I.; Petrov, A. A., Journal of general chemistry of the USSR, 1988, vol. 58, # 5, p. 859 - 871
  作者：Ryabov, B. V.、Ionin, B. I.、Petrov, A. A.

  DOI：——

  日期：——