2-(1-bromonaphthalen-2-yl)-2-methylpropanal | 1206451-05-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-bromonaphthalen-2-yl)-2-methylpropanal
• 英文别名: 2-(1-bromo-2-naphthyl)-2-methylpropanal
• CAS: 1206451-05-9
• 化学式: C₁₄H₁₃BrO
• 分子量: 277.161
• InChiKey: PLXLEOQJCICNLH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.08
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-(1-bromonaphthalen-2-yl)-2-methylpropanal 在 palladium diacetate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 1,4-二氧六环 为溶剂， 以64%的产率得到2,2-dimethylcyclobuta[a]naphthalen-1(2H)one
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C−H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones

  摘要：

  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.

  DOI：

  10.1021/ja909811t
• 作为产物：
  描述：

  2-(1-bromonaphthalen-2-yl)-2-methylpropanenitrile 在 二异丁基氢化铝 、 盐酸 、 水 作用下， 以 正己烷 、 二氯甲烷 、 乙酸乙酯 为溶剂， 以1.3 g的产率得到2-(1-bromonaphthalen-2-yl)-2-methylpropanal
  参考文献：
  名称：

  Pd-Catalyzed Intramolecular Acylation of Aryl Bromides via C−H Functionalization: A Highly Efficient Synthesis of Benzocyclobutenones

  摘要：

  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.

  DOI：

  10.1021/ja909811t

文献信息

• Palladium-Catalyzed Access to Benzocyclobutenone-Derived Ketonitrones via C(sp²)–H Functionalization
  作者：Jakub Brześkiewicz、Rafał Loska

  DOI：10.1021/acs.orglett.2c01317

  日期：2022.6.10

  The palladium-catalyzed C(sp2)–H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described. This method allows for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were readily demonstrated, illustrating the synthetic utility of the obtained

  描述了溴芳基醛硝酮的钯催化 C(sp 2 )–H 官能化，生成苯并环丁酮衍生的酮硝酮。该方法可以制备各种具有广泛官能团耐受性的四元酮硝酮。所形成的产物的下游转化很容易被证明，说明了所获得的苯并环丁酮衍生的硝酮在构建多环含氮支架方面的合成效用。