4-hydroxy-3-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde | 1242104-36-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-hydroxy-3-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde
• 英文别名: 4-Hydroxy-3-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde
• CAS: 1242104-36-4
• 化学式: C₁₃H₁₆O₃Si
• 分子量: 248.354
• InChiKey: CXCKQBHEKCBFLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.44
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {(methoxy)(3-butenyl)carbene}pentacarbonylchromium(0) 、 4-hydroxy-3-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde 以 1,4-二氧六环 为溶剂， 反应 25.0h， 以65%的产率得到4,6-Dimethoxy-5-trimethylsilyl-7,8-dihydrophenanthren-3-ol
  参考文献：
  名称：

  Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes

  摘要：

  The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with gamma,delta-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative. Only the extremely electron-withdrawing methanesulfonate group can prevent this process from occurring. The use of the base additive collidine resulted in a surprising yield enhancement but no other discernable effect on the course of the reaction. Dihydrophenanthrene formation was attributed to rapid dehydration after the opening of a benzo-oxanorbornene intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.117
• 作为产物：
  描述：

  5-Iod-vanillin 、 三甲基乙炔基硅 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到4-hydroxy-3-methoxy-2-(2-trimethylsilylethynyl)benzaldehyde
  参考文献：
  名称：

  Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes

  摘要：

  The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with gamma,delta-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative. Only the extremely electron-withdrawing methanesulfonate group can prevent this process from occurring. The use of the base additive collidine resulted in a surprising yield enhancement but no other discernable effect on the course of the reaction. Dihydrophenanthrene formation was attributed to rapid dehydration after the opening of a benzo-oxanorbornene intermediate. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.04.117

文献信息

• Electronic control of product distribution in the [5+5]-coupling of ortho-alkynylbenzaldehyde derivatives and γ,δ-unsaturated carbene complexes
  作者：Alejandro Camacho-Davila、Lalith S.R. Gamage、Zhipeng Wang、James W. Herndon

  DOI：10.1016/j.tet.2010.04.117

  日期：2010.7

  The coupling of highly oxygenated ortho-alkynylbenzaldehyde derivatives with gamma,delta-carbene complexes was evaluated systematically. In all of the electron-rich systems investigated the exclusive product of the reaction is the dihydrophenanthrene derivative. Only the extremely electron-withdrawing methanesulfonate group can prevent this process from occurring. The use of the base additive collidine resulted in a surprising yield enhancement but no other discernable effect on the course of the reaction. Dihydrophenanthrene formation was attributed to rapid dehydration after the opening of a benzo-oxanorbornene intermediate. (C) 2010 Elsevier Ltd. All rights reserved.