α-(Dimethoxyphosphinylmethyl)acrylsaeureethylester | 86242-49-1

• 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: α-(Dimethoxyphosphinylmethyl)acrylsaeureethylester
• 英文别名: ethyl 2-[(dimethoxyphosphoryl)methyl]-2-propenoate；Ethyl 2-(dimethoxyphosphorylmethyl)prop-2-enoate
• CAS: 86242-49-1
• 化学式: C₈H₁₅O₅P
• 分子量: 222.178
• InChiKey: PYRYUPCOKQYIKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  α-(Dimethoxyphosphinylmethyl)acrylsaeureethylester 在 草酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 20.0h， 以86%的产率得到
  参考文献：
  名称：

  失活的烯丙基膦酸酯和-膦酰胺酸酯的开环易位：获得带有酯基的二氢次膦氧化物

  摘要：

  描述了带有烷氧基羰基取代基的新的烯丙基膦酸酯和烯丙基膦酸酯的制备。两种基于P的前体均经过RCM处理。在这种情况下，测试并比较了几种Ru基催化剂，以制备新的oxa-和aza-dihydrophosphinine氧化物。根据催化剂的性质和反应条件，已经获得了对杂环和均二聚体。另外，在Ru促进的条件下，将同二聚体转化为六元环状膦酸酯和氨基磷酸酯。

  DOI：

  10.1016/j.tetlet.2015.12.033
• 作为产物：
  描述：

  2-羟甲基丙烯酸乙酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.33h， 生成 α-(Dimethoxyphosphinylmethyl)acrylsaeureethylester
  参考文献：
  名称：

  Asymmetric synthesis of 2-alkyl-3-phosphonopropanoic acid derivatives via Rh-catalyzed asymmetric hydrogenation

  摘要：

  The commercially available ferrocene-based diphosphine ligand (S-c,S-Fc)-TaniaPhos was found to be highly effective in the Rh-catalyzed asymmetric hydrogenation of 3-aryl-2-(phosphonomethyl)propenates. Excellent enantioselectivity (90-98% ee) and high catalytic activity (S/C up to 1000) have been achieved, which represents the best results reported so far. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.12.002

文献信息

• First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates
  作者：Marwa Ayadi、Haitham Elleuch、Emmanuel Vrancken、Farhat Rezgui

  DOI：10.3762/bjoc.12.290

  日期：——

  series of gamma-ketoallylphosphonates through a direct conversion of both primary and secondary Morita-Baylis-Hillman (MBH) alcohols by trialkyl phosphites with or without DMAP, used as additive, and under solvent-free conditions, is described herein for the first time. Subsequently, a highly regioselective Luche reduction of the primary phosphonate 2a (R = H) gave the corresponding gamma-hydroxyallylphosphonate

  本文描述了通过有或没有DMAP的亚磷酸三烷基酯直接和间接的森田-贝利利斯-拜耳-希尔曼（MBH）醇直接和间接的森田-贝利斯-希尔曼（MBH）醇直接合成一系列γ-酮烯丙基膦酸酯的方法，该方法用作无添加剂条件。首次。随后，对伯膦酸酯2a（R = H）进行高度区域选择性的卢氏还原，得到了相应的γ-羟基烯丙基膦酸酯5，后者在作为催化剂的二碘（15 mol％）存在下与甲苯磺胺进一步反应，得到了相应的SN2型产物6a-d的分离产率为63-70％。或者，醇5产生相应的乙酸酯7，其由Ce（III）介导，成功地转化为相应的γ-氨基烯丙基膦酸酯8a-d。
• NOUVELLES VOIES D'ACCES AUX 2-ETHOXYCARBONYLALLYLPHOSPHONATES
  作者：Hédi Mrabet、Hédi Zantour

  DOI：10.1080/10426500490257005

  日期：2004.1

  The Michaelis-Arbusov reaction (method A) and the nucleophilic addition of dialkylphosphites followed by Hoffman olefination (method B) represent two synthetic methods giving a variety of 2-ethoxycarbonylallyl-phosphonates 2, in good yields, from readily accessible ethyl 2-(N,N-dialkylaminomethyl) acrylates 1.

  Michaelis-Arbusov 反应（方法 A）和亚磷酸二烷基酯的亲核加成，然后是 Hoffman 烯化（方法 B）代表了两种合成方法，从容易获得的乙基 2-(N ,N-二烷基氨基甲基)丙烯酸酯 1.
• γ-Alkylsulfide phosphonates through the thia-Michael strategy
  作者：Abderrahmen Abdelli、Hedi M'rabet、Mohamed Lotfi Efrit、Anne Gaucher、Damien Prim

  DOI：10.1080/17415993.2014.951856

  日期：2014.11.2
• Versatile approach to densely substituted isoxazolines and pyrazolines: Focus on a quaternary carbon center as a constitutive feature
  作者：Abderrahmen Abdelli、Haythem Gharsa、Momtez Jmaï、Anne Gaucher、Mohamed Lotfi Efrit、Hedi M'rabet、Damien Prim

  DOI：10.1016/j.tetlet.2020.151958

  日期：2020.6

  A new family of isoxazolines has been obtained via 1,3-dipolar cycloaddition in good to high yields under mild conditions. Our approach focused on construction of the heterocyclic ring and direct access to a quaternary carbon center at position 5. The methodology has also been extended to pyrazoline analogues. The antibacterial activity of these compounds was evaluated, showing specific antibacterial activity against Staphylococcus aureus. Six members of these heterocycles exhibited MIC values of 4 mu g/mL. (C) 2020 Elsevier Ltd. All rights reserved.
• Analogs of phosphoenol pyruvate. 3. New synthetic approaches to .alpha.-(dihydroxyphosphinylmethyl)acrylic acid and unequivocal assignments of the vinyl protons in its nuclear magnetic resonance spectrum
  作者：Robert M. Davidson、George L. Kenyon

  DOI：10.1021/jo00426a022

  日期：1977.3