diethyl (1,2-cis-3,4-trans-4-phenylbuta-1,3-dienyl)phosphonate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diethyl (1,2-cis-3,4-trans-4-phenylbuta-1,3-dienyl)phosphonate
• 英文别名: diethyl (1Z,3E)-(4-phenyl-buta-1,3-dienyl)-phosphonate；diethyl (1Z,3E)-4-phenylbuta-1,3-dienylphosphonate；[(1E,3Z)-4-diethoxyphosphorylbuta-1,3-dienyl]benzene
• 化学式: C₁₄H₁₉O₃P
• 分子量: 266.277
• InChiKey: OIUKDTJORJBTKS-UQXQTEIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-苯基-2-丙烯-1-醇 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 4-二甲氨基吡啶 、 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 18.0h， 生成 diethyl (1,2-cis-3,4-trans-4-phenylbuta-1,3-dienyl)phosphonate
  参考文献：
  名称：

  Stereoselective Synthesis of Dienyl Phosphonates via Extended Tethered Ring-Closing Metathesis

  摘要：

  Allylphosphonates of allylic alcohols were converted to conjugated dienyl phosphonates in a one-flask reaction, comprising a ring-closing metathesis (RCM), a base-induced ring-opening, and an alkylation. The ring-opening proceeds with very high diastereoselectivity, giving exclusively the (1Z,3E)-configured dienes. Single diastereomers and mixtures of diastereomers can be used as starting materials without noticeable effect on the diastereoselectivity of the sequence.

  DOI：

  10.1021/ol4020078

文献信息

• A Convenient Stereoselective Synthesis of 1,3-Dienylphosphonates and 1-En-3-ynylphosphonates and Their Phosphine Oxide Analogs
  作者：Xiaoling Huang、Chunming Zhang、Xiyan Lu

  DOI：10.1055/s-1995-4000

  日期：1995.7

  Ethynylphosphonates (or phosphine oxides) react with a lithium halide in acetic acid at 70°C to yield (Z)-2-halovinylphosphonates (or phosphine oxides), which give (1Z,3E)-dienylphosphonates and (1Z)-en-3-ynylphosphonates (phosphine oxides) after coupling with alkenes and alkynes, respectively, in the presence of a palladium catalyst.

  乙炔基膦酸酯（或膦氧化物）在70°C的醋酸中与锂卤化物反应，生成(Z)-2-卤烯基膦酸酯（或膦氧化物），这些反应产物在钯催化剂的存在下，分别与烯烃和炔烃偶联，生成(1Z,3E)-二烯基膦酸酯和(1Z)-en-3-炔基膦酸酯（膦氧化物）。
• Preparation of New Wittig Reagents and Their Application to the Synthesis of α,β-Unsaturated Phosphonates
  作者：Yibo Xu、Michael T. Flavin、Ze-Qi Xu

  DOI：10.1021/jo9608275

  日期：1996.1.1

  The Wittig reagent [(diethoxyphosphinyl)methylidene]triphenylphosphorane (1b) has been successfully synthesized for the first time via its phosphonium triflate salt (4a), by treating (diethoxyphosphinyl)methyl triflate with triphenylphosphine. The procedure has been applied to the synthesis of other phosphoranes and phosphonium salts. The new Wittig reagents thus synthesized were treated with various

  通过用三苯基膦处理三氟甲磺酸（二乙氧基膦基）甲基三氟甲磺酸盐，已通过其三氟甲磺酸盐（4a）首次成功合成了Wittig试剂[（二乙氧基膦基）亚甲基]三苯基膦烷（1b）。该方法已应用于其他phosphor烷和phospho盐的合成。这样合成的新的Wittig试剂用各种醛和活化的酮处理，得到相应的α，β-不饱和膦酸酯。三苯基膦1b和三苯基4 4a导致顺式和反式异构体均以顺式为主，而当使用三丁基试剂（1c和4d）时，反式异构体几乎全部形成。
• 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
• Suzuki and Stille Cross-Coupling Reactions from β-Iodovinylphosphonate: Stereoselective Access to Various Substituted Vinylphosphonates
  作者：Mohamed Abarbri、Emilie Thiery

  DOI：10.1055/s-0034-1378360

  日期：——

  Stereoselective synthesis of beta-arylvinyl, dienyl, and enynylphosphonates was achieved from diethyl 2-iodovinylphosphonate via Suzuki or Stille cross-coupling reactions in good yields.