methyl [6-phenyl-2-{(trimethylsilyl)methyl}phenyl]methyl carbonate | 1182624-06-1

• 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 [6-phenyl-2-{(trimethylsilyl)methyl}phenyl]methyl carbonate
• 英文别名: Methyl [2-phenyl-6-(trimethylsilylmethyl)phenyl]methyl carbonate
• CAS: 1182624-06-1
• 化学式: C₁₉H₂₄O₃Si
• 分子量: 328.483
• InChiKey: DDNNKLPANBSLGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.06
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl [6-phenyl-2-{(trimethylsilyl)methyl}phenyl]methyl carbonate 、 N-亚苄基-4-甲基苯磺酰胺 在 potassium fluoride 、 allyl(cyclopentadiene)palladium(II) 、 1,5-双(二苯基膦)戊烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(4-methylbenzenesulfonyl)-3,5-diphenyl-1,2,3,4-tetrahydroisoquinoline 、 2-(4-methylbenzenesulfonyl)-3,8-diphenyl-1,2,3,4-tetrahydroisoquinoline
  参考文献：
  名称：

  [4+2] Cycloaddition of o-Xylylenes with Imines Using Palladium Catalyst

  摘要：

  The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(eta(3)-C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diets-Alder reaction of o-xylylene with imines.

  DOI：

  10.1021/ja905988e
• 作为产物：
  描述：

  [2-phenyl-6-{(trimethylsilyl)methyl}phenyl]methanol 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 以84%的产率得到methyl [6-phenyl-2-{(trimethylsilyl)methyl}phenyl]methyl carbonate
  参考文献：
  名称：

  [4+2] Cycloaddition of o-Xylylenes with Imines Using Palladium Catalyst

  摘要：

  The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(eta(3)-C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diets-Alder reaction of o-xylylene with imines.

  DOI：

  10.1021/ja905988e

文献信息

• Palladium-Catalyzed [4 + 2] Cycloaddition of <i>o</i>-(Silylmethyl)benzyl Esters with Ketones: An Equivalent to Oxo-Diels−Alder Reaction of <i>o</i>-Xylylenes
  作者：Satoshi Ueno、Masakazu Ohtsubo、Ryoichi Kuwano

  DOI：10.1021/ol101792a

  日期：2010.10.1

  o-(Silylmethyl)benzyl carbonates reacted with various electron-deficient ketones in the presence of a palladium catalyst, affording the [4 + 2] cycloaddition products, isochromanes, in high yields. The palladium-catalyzed cycloaddition is equivalent to the oxo-Diels−Alder reaction of o-xylylene with ketones. The regioselectivities were extraordinarily affected by the structures of the o-xylylene precursors

  在钯催化剂的存在下，邻-（甲硅烷基甲基）苄基碳酸酯与各种缺电子的酮反应，以高收率提供了[4 + 2]环加成产物异色烷。钯催化的环加成反应相当于邻二甲苯基与酮的oxo-Diels-Alder反应。区域选择性特别受邻二甲苯前体和酮的结构影响。异常的区域化学反应可能在催化反应中支持两个竞争性反应途径。
• [4+2] Cycloaddition of <i>o</i>-Xylylenes with Imines Using Palladium Catalyst
  作者：Satoshi Ueno、Masakazu Ohtsubo、Ryoichi Kuwano

  DOI：10.1021/ja905988e

  日期：2009.9.16

  The cycloaddition of o-(silylmethyl)benzylic carbonates with imines proceeded in the presence of the Pd(eta(3)-C3H5)Cp-DPPPent catalyst, affording the tetrahydroisoquinolines in good to high yields. The reaction rate was remarkably increased by a fluoride additive. In the catalytic cycloaddition, the palladium(0) reacted with the benzylic substrate to form 2-palladaindane, which works as an o-xylylene equivalent. The catalytic reaction is equivalent to the hetero-Diets-Alder reaction of o-xylylene with imines.