methyl 2-phenyl-2-(o-tolyl)acetate

• 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: methyl 2-phenyl-2-(o-tolyl)acetate
• 英文别名: methy 2-phenyl-2-(o-tolyl)acetate；Methyl 2-(2-methylphenyl)-2-phenylacetate
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: CJEBMSLZQUQSKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  methyl 2-diazo-2-(o-tolyl)acetate 、 苯基三甲氧基硅烷 在 [Rh(OH)(cod)]2 、 四丁基氟化铵 、 tricyclohexylphosphine tetrafluoroborate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 以68%的产率得到methyl 2-phenyl-2-(o-tolyl)acetate
  参考文献：
  名称：

  Rh(I)-Catalyzed Cross-Coupling of α-Diazoesters with Arylsiloxanes

  摘要：

  An Rh(I)-catalyzed cross-coupling of diazoesters with arylsiloxanes has been successfully achieved. This transformation is a new method for the construction of the C(sp(3))C(sp(2)) bond, thus providing an alternative synthesis of a-aryl esters. Rh(I)carbene migratory insertion has been proposed to be involved in this coupling reaction. The reaction represents the first example of utilizing arylsiloxane as the coupling partner in the carbene-involved cross-coupling reactions.

  DOI：

  10.1021/acs.orglett.5b00052

文献信息

• Novel reductive Friedel-Crafts alkylation of aromatics catalyzed by indium compounds: Chemoselective utilization of carbonyl moieties as alkylating reagents
  作者：Takashi Miyai、Yoshiyuki Onishi、Akio Baba

  DOI：10.1016/s0040-4020(98)01130-2

  日期：1999.1

  Reductive Friedel-Crafts alkylation of aromatics with ketones or aldehydes was characteristically catalyzed by indium compounds in preference to general catalysts like AlCl3 and BF3, where hydrosilanes would play an important role both as a hydride donor and as a co-catalyst. Chemoselective utilization of ketone moieties as alkylating reagents took place even in the presence of halogen, ester or ether

  铟化合物优先于一般催化剂（如AlCl 3和BF 3），其特征在于铟化合物可催化芳香族化合物与酮或醛的还原Friedel-Crafts烷基化反应，其中氢硅烷既可作为氢化物供体，又可作为助催化剂。甚至在卤素，酯或醚部分的存在下，酮部分作为烷基化试剂的化学选择性利用也发生了，在传统的弗瑞德-克拉夫茨条件下，卤素，酯或醚部分非常容易受到影响。通过一些受控实验对合理的中间体进行了讨论。
• Rhodium Catalyzed Arylation of Diazo Compounds with Aryl Boronic Acids
  作者：Jayanta Ghorai、Pazhamalai Anbarasan

  DOI：10.1021/jo502922r

  日期：2015.4.3

  general and efficient synthesis of diarylacetate, a diarylmethine derivative, was accomplished through rhodium catalyzed direct arylation of diazo compounds with arylboronic acids. The reaction tolerates various boronic acid derivatives and functional groups. Notably, chemoselective arylation of diazo compounds over other electrophiles were demonstrated. The efficacy of the developed methodology is shown

  通过铑催化的重氮化合物与芳基硼酸的直接芳基化反应，可以实现二芳基次甲基衍生物二芳基乙酸酯的一般有效合成。该反应可耐受各种硼酸衍生物和官能团。值得注意的是，证明了重氮化合物相对于其他亲电试剂的化学选择性芳基化。快速合成双氯芬素的核心结构表明了所开发方法的有效性。