diethyl pent-1-ynylphosphonate | 7579-98-8

• 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 pent-1-ynylphosphonate
• 英文别名: (Pentin-1-yl)-diethylphosphonat；Diaethyl-1-pentinylphosphonat；Phosphonic acid, 1-pentynyl-, diethyl ester；1-diethoxyphosphorylpent-1-yne
• CAS: 7579-98-8
• 化学式: C₉H₁₇O₃P
• 分子量: 204.206
• InChiKey: JRLHSEUAGGZRAT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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 pent-1-ynylphosphonate 在 5% Pd/CaCO3 喹啉 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以68%的产率得到(Z)-1-diethoxyphosphorylpent-1-ene
  参考文献：
  名称：

  乙烯基膦酸酯的简便和立体选择性合成

  摘要：

  从容易获得的烷基-1-炔基膦酸酯开始，已经开发出了立体选择性合成单，二和三取代的烷基-1-烯基膦酸酯的方法，该方法是使用催化加氢或在三键上加铜盐。

  DOI：

  10.1016/s0022-328x(96)06646-6
• 作为产物：
  描述：

  magnesium,pent-1-yne,bromide 、 氯磷酸二乙酯 以 乙醚 为溶剂， 生成 diethyl pent-1-ynylphosphonate
  参考文献：
  名称：

  Convenient synthesis of 1-alkynylphosphonates

  摘要：

  DOI：

  10.1021/jo00817a034

文献信息

• Cycloaddition of enamines with alkynylphosphonates. A route to functionalized medium sized rings
  作者：Suzanne M. Ruder、Bradley K. Norwood

  DOI：10.1016/s0040-4039(00)73213-8

  日期：1994.5

  seven and eight membered rings were formed from cyclopentanone and cyclo-hexanone via cycloadditions of pyrrolidine enamines with alkynyl phosphonates. This procedure provides straightforward access to functionalized medium sized rings that could be further manipulated in the synthesis of a number of natural products.

  通过吡咯烷烯胺与炔基膦酸酯的环加成反应，由环戊酮和环己酮形成七个和八个员环。该程序提供了对功能化中型环的直接访问，可以在合成多种天然产物时对其进行进一步操作。
• Sturtz,G. et al., Bulletin de la Societe Chimique de France, 1966, p. 1707 - 1713
  作者：Sturtz,G. et al.

  DOI：——

  日期：——
• Enamine phosphonates: Their use in the synthesis of α,β-ethylenic ketimines and the corresponding ketones
  作者：Mohinder S. Chattha、Adam M. Aguiar

  DOI：10.1016/s0040-4039(01)96725-5

  日期：1971.1
• Isomerization of Diethyl 1-Alkynylphosphonates to 1,3-Dienylphosphonates Followed by Diels-Alder Reaction with Dead, Maleic Anhydride and Maleimide
  作者：Morris Srebnik、Abdullatif Azab、Abed Al Aziz Quntar、Tamar Antebi

  DOI：10.3987/com-10-s(e)12

  日期：——

  Isomerization of diethyl 1-alkynylphosphonates, 1, with Pd[(PPh)(3)](4) in refluxing 1,4-dioxane provides 1,3-dienylphosphonates, 2, in satisfactory to excellent isolated yield (45-83%). The reaction is tolerant of chlorides and cyclic substituents. Cycloaddition reaction of 2 with DEAD provided the corresponding diethyl 3-(diethoxyphosphoryl)-6-alkyl-3,6-dihydropyridazine-1,2-dicarboxylates, 3, in 85% isolated yield. The cycloaddition products can be obtained in a one-pot reaction directly from the isomerized 1-alkynylphosphonates with no loss in yields. Similarly, 1,3-dioxo-1,3,3a,4,7,7a-hexahydroisobenzofuran-4-ylphosphonate, and 1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindo1-4-ylphosphonate 4 were obtained by reacting 1,3-dienylphosphonates with maleic anhydride and maleimide respectively.
• Direct formation of cyclobutenylphosphonates from 1-alkynylphosphonates and Cp2ZrCl2/2EtMgCl/2CuCl
  作者：Yulia Sinelnikove、Abraham Rubinstein、Morris Srebnik、Abed Al Aziz Al Quntar

  DOI：10.1016/j.tetlet.2008.11.108

  日期：2009.2

  Zirconacycles 2 prepared from 1-alkynylphosphonates 1, zirconocene dichloride, and 2 equiv of EtMgCl are smoothly converted into cyclobutenylphosphonates 3 when treated with two equiv of CuCl in 65-81% isolated yield. The reaction is specific and general only for zirconacyclopentenyl phosphonates. (C) 2008 Elsevier Ltd. All rights reserved.