2-(2-iodophenyl)-2-methylpropanal | 1151654-07-7

• 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: 2-(2-iodophenyl)-2-methylpropanal
• 英文别名: 2-(2-Iodophenyl)-2-methylpropanal
• CAS: 1151654-07-7
• 化学式: C₁₀H₁₁IO
• 分子量: 274.101
• InChiKey: PQROZPWMJDUVNV-UHFFFAOYSA-N

物化性质

• 沸点：
  298.8±23.0 °C(Predicted)
• 密度：
  1.561±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(2-iodophenyl)-2-methylpropanal 在 palladium diacetate 、 cesium pivalate 、 双二苯基膦甲烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以39%的产率得到2-苯基-1-丙烯
  参考文献：
  名称：

  Studies in Acyl C−H Activation via Aryl and Alkyl to Acyl “Through Space” Migration of Palladium

  摘要：

  Examples of the 1,4-migration of a palladium moiety in aryl- and alkylpalladium intermediates to the acyl position of an aldehyde or formamide have been observed. The resulting acylpalladium intermediate can undergo ester or carbamate formation by reaction with an alcohol; decarbonylation, followed by beta hydride elimination to an alkene; reaction with an organomercurial to form an ester; or alkene insertion. Deuterium-labeling studies have been used to confirm the palladium migration mechanism.

  DOI：

  10.1021/ol900940k
• 作为产物：
  描述：

  2-o-iodophenyl-2-methylpropanenitrile 在 二异丁基氢化铝 、 硫酸 、 水 作用下， 以 二氯甲烷 为溶剂， -78.0~20.0 ℃ 、2.67 kPa 条件下， 生成 2-(2-iodophenyl)-2-methylpropanal
  参考文献：
  名称：

  Studies in Acyl C−H Activation via Aryl and Alkyl to Acyl “Through Space” Migration of Palladium

  摘要：

  Examples of the 1,4-migration of a palladium moiety in aryl- and alkylpalladium intermediates to the acyl position of an aldehyde or formamide have been observed. The resulting acylpalladium intermediate can undergo ester or carbamate formation by reaction with an alcohol; decarbonylation, followed by beta hydride elimination to an alkene; reaction with an organomercurial to form an ester; or alkene insertion. Deuterium-labeling studies have been used to confirm the palladium migration mechanism.

  DOI：

  10.1021/ol900940k

文献信息

• Palladium‐Catalyzed Intermolecular [4+1] Spiroannulation by C(sp ³ )−H Activation and Naphthol Dearomatization
  作者：Bojun Tan、Lu Bai、Pin Ding、Jingjing Liu、Yaoyu Wang、Xinjun Luan

  DOI：10.1002/anie.201813202

  日期：2019.1.28

  was developed by using a C(sp3)−H activation/naphthol dearomatization approach. This bimolecular domino reaction of two aryl halides was realized through a sequence of cyclometallation‐facilitated C(sp3)−H activation, biaryl cross‐coupling, and naphthol dearomatization, thus rendering the rapid assembly of a new class of spirocyclic molecules in good yields with broad functional‐group tolerance. Preliminary

  通过使用C（sp 3）-H活化/萘脱芳香化方法，开发了一种新型的钯催化的[4 + 1]螺环。两个芳基卤化物的双分子多米诺反应是通过一系列环金属化促进的C（sp 3）-H活化，联芳基交叉偶联和萘酚脱芳香化作用实现的，从而使新型螺环分子快速组装并获得了高收率具有广泛的功能组容忍度。初步的机理研究表明，CH裂解可能参与了速率确定步骤，并且五元的palladacycle被确定为分子间偶联的关键中间产物。
• Studies in Acyl C−H Activation via Aryl and Alkyl to Acyl “Through Space” Migration of Palladium
  作者：Tanay Kesharwani、Akhilesh K. Verma、Daniel Emrich、Jeffrey A. Ward、Richard C. Larock

  DOI：10.1021/ol900940k

  日期：2009.6.18

  Examples of the 1,4-migration of a palladium moiety in aryl- and alkylpalladium intermediates to the acyl position of an aldehyde or formamide have been observed. The resulting acylpalladium intermediate can undergo ester or carbamate formation by reaction with an alcohol; decarbonylation, followed by beta hydride elimination to an alkene; reaction with an organomercurial to form an ester; or alkene insertion. Deuterium-labeling studies have been used to confirm the palladium migration mechanism.