diethyl (E)-(2-naphthalen-1-yl-vinyl)-phosphonate | 202476-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl (E)-(2-naphthalen-1-yl-vinyl)-phosphonate
• 英文别名: diethyl (E)-2-(1-naphthyl)ethenylphosphonate；1-[(E)-2-diethoxyphosphorylethenyl]naphthalene
• CAS: 202476-40-2
• 化学式: C₁₆H₁₉O₃P
• 分子量: 290.299
• InChiKey: BOWCPBAVKAVZDX-OUKQBFOZSA-N

物化性质

• 沸点：
  431.0±28.0 °C(predicted)
• 密度：
  1.156±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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 (E)-(2-naphthalen-1-yl-vinyl)-phosphonate 在 ammonium hydroxide 、 四丁基硫酸氢铵 、 peroxomonosulfate(1-) 作用下， 以 甲醇 、 水 、 丁酮 为溶剂， 反应 22.0h， 生成 ((1S,2R)-2-Amino-1-hydroxy-2-naphthalen-1-yl-ethyl)-phosphonic acid diethyl ester
  参考文献：
  名称：

  区域和立体选择性合成2-氨基-1-羟基-2-芳基乙基膦酸酯

  摘要：

  通过用含28％NH 3（aq。）的甲醇溶液打开反式1,2-环氧-2-芳基乙基膦酸酯，可以实现2-氨基-1-羟基-2-芳基乙基膦酸酯的高度区域选择性和非对映选择性的合成。

  DOI：

  10.1016/s0040-4039(00)01722-6
• 作为产物：
  描述：

  1-萘硼酸 、 乙烯基磷酸二乙酯 在 palladium diacetate 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以66%的产率得到diethyl (E)-(2-naphthalen-1-yl-vinyl)-phosphonate
  参考文献：
  名称：

  通过芳基硼酸与乙烯基二膦酸二乙酯的Mizoroki-Heck反应，方便地合成α，β-不饱和膦酸酯

  摘要：

  乙酸钯催化的芳基硼酸与乙烯基膦酸二乙酯的Mizoroki-Heck反应可得到高产率的α，β-不饱和膦酸酯。

  DOI：

  10.1016/j.tetlet.2004.04.094

文献信息

• 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
• Base-Free Mizoroki−Heck Reaction Catalyzed by Rhodium Complexes
  作者：Rémi Martinez、Florina Voica、Jean-Pierre Genet、Sylvain Darses

  DOI：10.1021/ol071098q

  日期：2007.8.1

  A base-free rhodium-catalyzed Mizoroki-Heck (M-H) reaction using potassium aryltrifluoroborates as the arylating agent of alkenes and acetone as a green '' oxidant '' is described. Thanks to the ready availability of organoboranes, this reaction should constitute an interesting alternative to conventional M-H reactions using aryl halides.
• Enantioselective synthesis of threo-α,β-dihydroxyphosphonates by asymmetric dihydroxylation of 1(E)-alkenylphosphonates with AD-mix reagents
  作者：Tsutomu Yokomatsu、Takehiro Yamagishi、Kenji Suemune、Yoshinori Yoshida、Shiroshi Shibuya

  DOI：10.1016/s0040-4020(97)10341-6

  日期：1998.1

  Asymmetric dihydroxylation (AD) of 1(E)-alkenylphosphonates with an AD-mix -alpha or -beta reagent was examined to give a series of optically active threo-alpha,beta-dihydroxyphosphonates. Good enantioselectivity (>88% eel was observed in the AD reaction of 1(E)-alkenylphosphonates with conjugated aromatic substituents. The steric effects of the ester functionality in the course of the dihydroxylation were also evaluated. Enantioselectivity and yield were significantly improved when the AD reaction was carried out with dimethyl phosphonate instead of diethyl phosphonate. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis of α-aminoalkylphosphonates from vinylphosphonates via aziridinylphosphonates
  作者：Dae Young Kim、Dae Yong Rhie

  DOI：10.1016/s0040-4020(97)00880-6

  日期：1997.10