diethyl (E)-2-(furan-2-yl)vinylphosphonate | 71755-92-5

• 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 (E)-2-(furan-2-yl)vinylphosphonate
• 英文别名: diethyl <2-(2-furyl)vinyl>phosphonate；2-[(E)-2-diethoxyphosphorylethenyl]furan
• CAS: 71755-92-5
• 化学式: C₁₀H₁₅O₄P
• 分子量: 230.2
• InChiKey: MIWDBNGXLUHHFZ-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl (E)-2-(furan-2-yl)vinylphosphonate 在 甲醇 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 diethyl 2-(2-furyl)ethanphosphonate
  参考文献：
  名称：

  Photo-oxidation of 2-furyl-alkyl-phosphonates: Synthesis of new cyclopentenone derivatives

  摘要：

  The furan ring in the title compounds was opened with singlet oxygen in methanol. New phosphonate cyclopentenone derivatives were synthesized.

  DOI：

  10.1016/0040-4020(95)00125-r
• 作为产物：
  描述：

  甲基膦酸二乙酯 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 生成 diethyl (E)-2-(furan-2-yl)vinylphosphonate
  参考文献：
  名称：

  A Facile Preparation of 2-Arylethenephosphonates

  摘要：

  Vinylphosphonates 3 could be prepared with E-selectivity by the condensation of diethyl methylyhosphonate 1 with a series of carbonyl compounds using diethyl chlorophosphate.

  DOI：

  10.1080/00397919508015879

文献信息

• Diastereoselective Synthesis of 2-Amino-4-phosphonobutanoic Acids by Conjugate Addition of Lithiated Schöllkopf's Bislactim Ethers to Vinylphosphonates
  作者：María Ruiz、M. Carmen Fernández、Aniana Díaz、José M. Quintela、Vicente Ojea

  DOI：10.1021/jo034707q

  日期：2003.10.1

  Conjugate additions of lithiated bislactim ethers derived from cyclo-[Gly-Val] and cyclo-[Ala-Val] to alpha-, beta-, or alpha,beta-substituted vinylphosphonates allow direct and stereoselective access to a variety of 3- or 4-monosubstituted and 2,3-, 2,4-, or 3,4-disubstituted 2-amino-4-phosphonobutanoic acids (AP4 derivatives) in enantiomerically pure form. The relative stereochemistry was assigned

  将衍生自环-[Gly-Val]和环-[Ala-Val]的锂化双lactimin醚与α-，β-或α，β-取代的乙烯基膦酸酯共轭加成可直接和立体选择性地获得各种3-或4对映体纯形式的-单取代和2,3-，2,4-或3,4-二取代的2-氨基-4-膦酰基丁酸（AP4衍生物）。通过X-射线衍射分析或1，2-氧杂磷杂环丁烷衍生物的NMR研究确定相对立体化学。调用竞争性的八元“紧凑”和“松弛”过渡态结构以合理化共轭添加物的立体化学结果。
• A new route to α-fluorovinylphosphonates utilizing Peterson olefination methodology
  作者：Rachel Waschbüsch、John Carran、Philippe Savignac

  DOI：10.1016/0040-4020(96)00859-9

  日期：1996.11

  Several α-fluorovinylphosphonates (6) have been synthesised from the Peterson olefination reaction applied to both aldehydes and ketones in conjunction with α-lithiated-α-fluoro-α-trimethylsilylmethylphosphonate (2). The reaction with aldehydes gives mainly the E-isomer whereas reaction with ketones gives mainly the Z-isomer. We propose a closed transition state to explain the results of our study

  几个α-fluorovinylphosphonates（6）已经从施加到两个醛和酮结合α-锂化-α氟-α-trimethylsilylmethylphosphonate（Peterson烯反应，合成2）。与醛的反应主要产生E-异构体，而与酮的反应主要产生Z-异构体。我们提出了一个封闭的过渡状态来解释我们的研究结果。
• Manganese(<scp>iii</scp>)-mediated alkenyl C_sp2–P bond formation from the reaction of β-nitrostyrenes with dialkyl phosphites
  作者：Jian-Fei Xue、Shao-Fang Zhou、Ye-Ye Liu、Xiangqiang Pan、Jian-Ping Zou、Olayinka Taiwo Asekun

  DOI：10.1039/c5ob00404g

  日期：——

  Mn(OAc)₃-mediated tandem phosphonyl radical addition to β-nitrostyrenes followed by denitration to form (E)-2-alkenyl phosphonates is described.

  通过Mn(OAc)₃介导的串联磷酰基自由基加成到β-硝基苯乙烯，然后脱硝形成(E)-2-烯基磷酸酯。
• Knoevenagel Reaction of Diethylphosphonoacetic Acid: A Facile Route to Diethyl (<i>E</i>)-2-Arylvinylphosphonates
  作者：Henryk Krawczyk、Łukasz Albrecht

  DOI：10.1055/s-2005-918406

  日期：——

  Knoevenagel reaction of aromatic aldehydes or a-substituted aliphatic aldehydes with diethylphosphonoacetic acid leads to the formation of 3-substituted-2-(diethoxyphosphoryl)acrylic acids. Decarboxylation of the resulting (E)-3-aryl-2-(diethoxyphosphoryllacrylic acids afforded diethyl (E)-2-arylvinylphosphonates. Direct synthesis of diethyl vinylphosphonates from some aromatic aldehydes and formaldehyde

  芳族醛或α-取代的脂肪醛与二乙基膦酰基乙酸的Knoevenagel反应导致形成3-取代的-2-(二乙氧基磷酰基)丙烯酸。得到的 (E)-3-aryl-2-(二乙氧基磷酰丙烯酸) 脱羧得到 (E)-2-arylvinylphosphonates 二乙基酯。还报道了从一些芳香醛和甲醛直接合成二乙基乙烯基膦酸酯。
• Reaction of diethyl thiocyanatomethylphosphonate with aldehydes as a route to diethylZ-1-alkenylphosphonates
  作者：Roman Błaszczyk、Tadeusz Gajda

  DOI：10.1002/hc.20371

  日期：2007.11

  Diastereoselective synthesis of diethyl Z-1-alkenylphosphonates from easily available diethyl thiocyanatomethylphosphonate and aromatic aldehydes has been developed. Olefination of the aldehydes occurs under mild conditions and affords the title compounds with moderate yields. A plausible mechanism of the above-mentioned reaction is also discussed. © 2007 Wiley Periodicals, Inc. Heteroatom Chem 18:732–739

  已经开发了从容易获得的硫氰基甲基膦酸二乙酯和芳香醛中非对映选择性合成 Z-1-烯基膦酸二乙酯。醛的烯烃化在温和条件下发生并以中等产率提供标题化合物。还讨论了上述反应的合理机制。© 2007 Wiley Periodicals, Inc. 杂原子化学 18:732–739, 2007; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.20371