diethyl (propa-1,2-dienyl)phosphonate | 1609-72-9

• 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: diethyl (propa-1,2-dienyl)phosphonate
• 英文别名: diethyl propa-1,2-diene-1-ylphosphonate；Diethyl propadienylphosphonate
• CAS: 1609-72-9
• 化学式: C₇H₁₃O₃P
• 分子量: 176.152
• InChiKey: HSTDWLTWVXEIPZ-UHFFFAOYSA-N

物化性质

• 沸点：
  86 °C(Press: 0.9 Torr)
• 密度：
  1.092 g/cm3(Temp: 21 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl (propa-1,2-dienyl)phosphonate 在 palladium dihydroxide 氢气 、 lithium trifluoroacetate 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 indole-2-methylphosphonate de diethyle
  参考文献：
  名称：

  Hetero- Cope -Umlagerungen。4. Mitteilung。印多尔合成神父（Regiokontrollierte Indolsynthesen）†

  摘要：

  杂种应对重排，区域控制的吲哚合成

  DOI：

  10.1002/hlca.19850680705
• 作为产物：
  描述：

  phosphorous acid diethyl ester prop-2-ynyl ester 以 乙醚 为溶剂， 生成 diethyl (propa-1,2-dienyl)phosphonate
  参考文献：
  名称：

  Pudovik,A.N. et al., Journal of general chemistry of the USSR, 1965, vol. 35, p. 1214 - 1220

  摘要：

  DOI：

文献信息

• Regio- and Stereoselective Addition of Perfluoroalkyl Iodides to Allenes Conjugated with Carbon-Oxygen or Phosphorus-Oxygen Double Bonds
  作者：Jin-Tao Liu、Ying-Qiao Mei、Zhen-Jiang Liu

  DOI：10.1055/s-2007-965908

  日期：2007.3

  or a phosphorus-oxygen double bond, such as allenic phosphonates, phosphine oxides and allenecarboxylates, reacted readily with perfluoroalkyl iodides at room temperature to give the corresponding addition products in moderate yields with complete regioselectivity and stereoselectivity. Perfluoroalkyl groups were introduced into the terminal position of allenes and addition products with the E-configuration

  在连二亚硫酸钠存在下，与碳-氧或磷-氧双键共轭的丙二烯，例如丙二烯膦酸盐、氧化膦和丙二烯羧酸盐，在室温下容易与全氟烷基碘反应，以中等收率得到相应的加成产物完全的区域选择性和立体选择性。将全氟烷基引入丙二烯的末端位置，通过该反应选择性地获得具有E-构型的加成产物。
• Palladium(0)-Catalyzed Highly Regio- and Stereoselective Addition of Organoboronic Acids with 1,2-Allenylphosphonates Forming Tri- or Tetrasubstituted 1(<i>E</i>)-Alkenylphosphonates
  作者：Shengming Ma、Hao Guo、Fei Yu

  DOI：10.1021/jo060672t

  日期：2006.8.1

  A highly regio- and stereoselective palladium(0)-catalyzed addition of organoboronic acids with 1,2-allenylphosphonates in the presence of HOAc forming tri- or tetrasubstituted 1(E)-alkenylphosphonates is reported in this paper. The stereoselectivity is much higher than the reported cases. The effects of different R1, R2, and R3 were studied. A mechanism of this reaction is proposed on the basis of

  本文报道了在HOAc的存在下，高区域选择性和立体选择性钯（0）催化的有机硼酸与1,2-烯基膦酸酯的加成反应，形成三或四取代的1（E）-烯基膦酸酯。立体选择性远高于报道的情况。研究了不同的R 1，R 2和R 3的影响。在我们以前的研究的基础上，提出了这种反应的机理。
• Nickel-catalyzed, ligand-free, diastereoselective synthesis of 3-methyleneindan-1-ols
  作者：Heena Panchal、Christopher Clarke、Charles Bell、Somnath Narayan Karad、William Lewis、Hon Wai Lam

  DOI：10.1039/c8cc06388e

  日期：——

  Nickel-catalyzed, highly diastereoselective annulations between activated allenes and 2-acetylarylboronic acid or 2-formylarylboronic acids are reported. No ligand for nickel is required, and the reactions proceed efficiently at room temperature to give a broad range of substituted 3-methyleneindan-1-ols. Preliminary results of an enantioselective variant are also described.

  据报道，活化的烯与2-乙酰基芳基硼酸或2-甲酰基芳基硼酸之间存在镍催化的高度非对映选择性环。不需要镍的配体，并且反应在室温下有效地进行，从而得到广泛范围的取代的3-亚甲基茚满-1-醇。还描述了对映选择性变体的初步结果。
• An effective strategy for the preparation of (α,β-unsaturated hydrazones and pyrazole derivatives. Synthetic applications of β-functionalized phosphorus compounds.
  作者：Francisco Palacios、Domitila Aparicio、Jesús M. de los Santos

  DOI：10.1016/s0040-4020(01)89404-7

  日期：1994.1

  phosphonium salts 3 as web as β-hydrazano phosphine oxides 6 and phosphonates 7 are obtained from hydrazines, propargylphosphonium salts 2 and phosphorylated allenes 4 and 5. β-Functionalized compounds 3,6 and 7 are used for the synthesis of α,β-unsaturated hydrazones 1, pyrazoline 14 and pyrazole derivative 15.

  β-Enehydrazino鏻盐3作为网络为β-hydrazano氧化膦6和膦酸酯7选自肼获得，propargylphosphonium盐2和磷酸化丙二烯4和5。β官能化合物3，6和7是用于α，β不饱和腙的合成1，吡唑啉14和吡唑衍生物15。
• Novel, Stereoselective and Stereospecific Synthesis of Allenylphosphonates and Related Compounds via Palladium-Catalyzed Propargylic Substitution
  作者：Marcin Kalek、Jacek Stawinski

  DOI：10.1002/adsc.201100119

  日期：2011.7

  allenylphosphonates and related compounds based on a palladium(0)‐catalyzed reaction of propargylic derivatives with H‐phosphonate, H‐phosphonothioate, H‐phosphonoselenoate, and H‐phosphinate esters. The reaction is stereoselective and stereospecific, and provides a convenient entry to a vast array of allenylphosphonates and their analogues with diverse substitution patterns in the allenic moiety and at the phosphorus

  我们开发了一种新的合成烯丙基膦酸酯和相关化合物的方法，该方法基于钯（0）催化的炔丙基衍生物与H-膦酸酯，H-膦酰硫代酸酯，H-膦酰基油酸酯和H-膦酸酯的反应。该反应是立体选择性的和立体特异性的，并且提供了进入大量烯丙基膦酸酯及其类似物的便利入口，所述烯丙基膦酸酯及其类似物在所述烯丙基部分和在磷中心具有不同的取代模式。还研究了这种新反应的一些机理方面。