2-(3-(tert-butyldimethylsilyloxy)propyl)-2-propylcyclobutabenzen-1(2H)-one | 1206451-36-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-(3-(tert-butyldimethylsilyloxy)propyl)-2-propylcyclobutabenzen-1(2H)-one
• 英文别名: 8-[3-[Tert-butyl(dimethyl)silyl]oxypropyl]-8-propylbicyclo[4.2.0]octa-1,3,5-trien-7-one
• CAS: 1206451-36-6
• 化学式: C₂₀H₃₂O₂Si
• 分子量: 332.558
• InChiKey: SUPBOFKKZCNEBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-(tertbutyldimethylsilyloxy)-2-(2-chlorophenyl)-2-propylpentanal 在 1,3-双(1-金刚烷基)咪唑四氟硼酸盐 、 (2-methylallyl)palladium-chloride dimer 、 烯丙基醚 、 caesium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 14.0h， 以81%的产率得到2-(3-(tert-butyldimethylsilyloxy)propyl)-2-propylcyclobutabenzen-1(2H)-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Dichotomy in Pd-Catalyzed Acylation of Aryl Chlorides via C–H Bond Functionalization

  摘要：

  The first Pd-catalyzed intramolecular acylation of aryl chlorides via C-H bond functionalization is presented. The method allows for the synthesis of a variety of elusive benzocyclobutenones with a wide range of functional groups and substitution patterns. We demonstrate that a change in the ligand backbone dictates the selectivity pattern.

  DOI：

  10.1021/ol3023819

文献信息

• Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C−H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones
  作者：Paula Álvarez-Bercedo、Areli Flores-Gaspar、Arkaitz Correa、Ruben Martin

  DOI：10.1021/ja909811t

  日期：2010.1.20

  A new catalyst system for the intramolecular acylation of aldehydes with aryl bromides via C-H functionalization is described. The transformation is distinguished by a remarkable functional group tolerance and hence allows for the synthesis of a wide variety of highly functionalized benzocyclobutenones with a diverse set of substitution patterns from simple and easily accessible precursors.
• Synthesis of 8,8-Dipropylbicyclo[4.2.0]octa-1,3,5-trien-7-one via Pd-catalyzed Intramolecular C-H Bond-Acylation
  作者：Martin, Ruben、Flores-Gaspar, Areli

  DOI：10.15227/orgsyn.089.0159

  日期：——