methyl 2-(2-oxo-1,2-diphenylethyl)acrylate | 1170666-69-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 2-(2-oxo-1,2-diphenylethyl)acrylate
• 英文别名: Methyl 2-methylidene-4-oxo-3,4-diphenylbutanoate；methyl 2-methylidene-4-oxo-3,4-diphenylbutanoate
• CAS: 1170666-69-9
• 化学式: C₁₈H₁₆O₃
• 分子量: 280.323
• InChiKey: BXOHKGGZSMOJGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 2-(2-oxo-1,2-diphenylethyl)acrylate 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 5.33h， 生成 1-benzyl-5-methoxy-3-methyl-4,5-diphenyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts

  摘要：

  以 MBH 加合物为起点，我们开发出了多种 5-羟基-3-吡咯啉-2-酮衍生物的高效合成方法。此外，还证明了所制备的 5-羟基-3-吡咯啉-2-酮的一些合成适用性，包括合成内酰胺融合的四氢异喹啉。

  DOI：

  10.5012/bkcs.2012.33.5.1622
• 作为产物：
  描述：

  4-hydroxy-2-methylene-3,4-diphenylbutyric acid methyl ester 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以90%的产率得到methyl 2-(2-oxo-1,2-diphenylethyl)acrylate
  参考文献：
  名称：

  Facile synthesis of γ-alkenylbutenolides from Baylis–Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation

  摘要：

  Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.09.125

文献信息

• Facile synthesis of γ-alkenylbutenolides from Baylis–Hillman adducts: consecutive in-mediated Barbier allylation, PCC oxidation, isomerization, and Zn-mediated Barbier allylation
  作者：Jin Woo Lim、Ko Hoon Kim、Bo Ram Park、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.09.125

  日期：2011.12

  Alkenylbutenolides were synthesized regioselectively in good to moderate yields from Baylis-Hillman adducts via a consecutive indium-mediated Barbier type reaction between Baylis-Hillman bromide and aldehyde, PCC oxidation of the homoallylic alcohol, double bond isomerization, and zinc-mediated Barbier type alkenylation protocol. (C) 2011 Elsevier Ltd. All rights reserved.
• Vinyl Triphenylphosphonium Salt–Mediated Synthesis of Functionalized Alkenes
  作者：Sakineh Asghari、Fahimeh Molaee、Samaneh Ramezani

  DOI：10.1080/10426500903348047

  日期：2010.8.25

  Deoxybenzoin undergoes a smooth reaction with acetylenic esters in the presence of triphenylphosphine to produce phosphorus ylides. Only the tert-butyl phosphorus ylide undergoes an intramolecular Wittig reaction to produce highly strained cyclobutenes in boiling toluene, which spontaneously undergoes ring-opening reactions to produce highly functionalized 1,3-dienes. The unstable ylides undergo a 1,2-proton transfer and the loss of PPh3 to produce functionalized alkenes.
• An Efficient Synthesis of Various γ-Substituted Butenolides from Morita-Baylis-Hillman Adducts
  作者：Jin-Woo Lim、Ko-Hoon Kim、Se-Hee Kim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2012.33.5.1781

  日期：2012.5.20
• Facile Synthesis of 5-Hydroxy-3-pyrrolin-2-ones from Morita-Baylis-Hillman Adducts
  作者：Cheol-Hee Lim、Sung-Hwan Kim、Jae-Nyoung Kim

  DOI：10.5012/bkcs.2012.33.5.1622

  日期：2012.5.20

  An efficient synthetic method of various 5-hydroxy-3-pyrrolin-2-one derivatives has been developed starting from the MBH adducts. In addition, some synthetic applicability of the prepared 5-hydroxy-3-pyrrolin-2-ones was demonstrated including the synthesis of lactam-fused tetrahydroisoquinolines.

  以 MBH 加合物为起点，我们开发出了多种 5-羟基-3-吡咯啉-2-酮衍生物的高效合成方法。此外，还证明了所制备的 5-羟基-3-吡咯啉-2-酮的一些合成适用性，包括合成内酰胺融合的四氢异喹啉。