Diethyl <2-(4-methoxyphenyl)ethyl>phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: Diethyl <2-(4-methoxyphenyl)ethyl>phosphonate
• 英文别名: diethyl <2-(4-metoxyphenyl)ethyl>phosphonate；diethyl (4-methoxyphenethyl)phosphonate；diethyl 2-(4-methoxyphenyl)ethylphosphonate；1-(2-Diethoxyphosphorylethyl)-4-methoxybenzene
• 化学式: C₁₃H₂₁O₄P
• 分子量: 272.281
• InChiKey: IYZGGORLOSSCLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(Z)-2-chloro-2-diethoxyphosphorylethenyl]-4-methoxybenzene 以91%的产率得到
  参考文献：
  名称：

  Lowen Gregory T., Almond Merrick R., J. Org. Chem, 59 (1994) N 16, S 4548-4550

  摘要：

  DOI：

文献信息

• Nickel-catalyzed coupling of R₂P(O)Me (R = aryl or alkoxy) with (hetero)arylmethyl alcohols
  作者：Wei-Ze Li、Zhong-Xia Wang

  DOI：10.1039/d1ob00086a

  日期：——

  α-Alkylation of methyldiarylphosphine oxides with (hetero)arylmethyl alcohols was performed under nickel catalysis. Various arylmethyl and heteroarylmethyl alcohols can be used in this transformation. A series of methyldiarylphosphine oxides were alkylated with 30–90% yields. Functional groups on the aromatic rings of methyldiarylphosphine oxides or arylmethyl alcohols including OMe, NMe2, SMe, CF3, Cl, and

  在镍催化下，甲基二芳基膦氧化物与（杂）芳基甲醇的α-烷基化反应。在该转化中可以使用各种芳基甲基和杂芳基甲基醇。一系列甲基二芳基膦氧化物被烷基化，收率30-90％。可以容许甲基二芳基氧化膦或芳基甲醇的芳环上的官能团包括OMe，NMe 2，SMe，CF 3，Cl和F基团。该条件也适合于二烷基甲基膦酸酯的α-烷基化反应。
• Tashtoush, Hasan I.; Sustmann, Reiner, Chemische Berichte, 1993, vol. 126, # 7, p. 1759 - 1762
  作者：Tashtoush, Hasan I.、Sustmann, Reiner

  DOI：——

  日期：——
• Rh-Catalyzed Negishi Alkyl-Aryl Cross-Coupling Leading to α- or β-Phosphoryl-Substituted Alkylarenes
  作者：Hideki Takahashi、Shinya Inagaki、Naoko Yoshii、Fuxing Gao、Yasushi Nishihara、Kentaro Takagi

  DOI：10.1021/jo900142b

  日期：2009.4.3

  The catalytic cross-coupling between ArZnX and ICH2(CH2)(n)P(O)(OEt)(2) (n = 0-3) has been investigated to determine the utility of the Rh catalyst during the alkyl-aryl cross-coupling and to develop a new synthetic method for phosphoryl-substituted alkylarenes. Rh-dppf exhibits an excellent catalytic activity for the reaction with the alkylphosphonate of n = 1, whereas for the reaction with those of n = 2 or 3, P-hydride elimination mainly takes place. As for the reaction with an alkylphosphonate of n = 0, a polarity inversion of the coupling components is necessary in order to provide the coupling products; the phosphoryl analogue of the Reformatsky reagent and ArI give the cross-coupling products in good yields through the catalysis by Rh-dppf.
• A Novel Synthesis of Phosphonates from Diethyl (Trichloromethyl)phosphonate
  作者：Gregory T. Lowen、Merrick R. Almond

  DOI：10.1021/jo00095a033

  日期：1994.8

  Commercially available diethyl (1,1,1-trichloromethyl)phosphonate was reacted with aldehydes and ketones to generate (chlorovinyl)phosphonates in a single step. These intermediates could be hydrogenated in high yields to the corresponding saturated phosphonates.