2-methyl-1-(trimethoxysilyloxy)-3,4-dihydronaphthalene | 1379003-20-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-methyl-1-(trimethoxysilyloxy)-3,4-dihydronaphthalene
• 英文别名: Trimethyl (2-methyl-3,4-dihydronaphthalen-1-yl) silicate；trimethyl (2-methyl-3,4-dihydronaphthalen-1-yl) silicate
• CAS: 1379003-20-9
• 化学式: C₁₄H₂₀O₄Si
• 分子量: 280.396
• InChiKey: IYEYMGSLAWADKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-1-(trimethoxysilyloxy)-3,4-dihydronaphthalene 、 苯甲醛 在 (R)-3,3'-dichloro-1,1'-binaphthalene-2,2'-diol lithium salt 、 potassium fluoride 、 甲酸 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 5.0h， 生成 (2R)-2-[(S)-hydroxy(phenyl)methyl]-2-methyl-3,4-dihydronaphthalen-1-one 、 (2S)-2-[(R)-hydroxy(phenyl)methyl]-2-methyl-3,4-dihydronaphthalen-1-one 、 (2R)-2-[(R)-hydroxy(phenyl)methyl]-2-methyl-3,4-dihydronaphthalen-1-one 、 (2S)-2-[(S)-hydroxy(phenyl)methyl]-2-methyl-3,4-dihydronaphthalen-1-one
  参考文献：
  名称：

  Construction of quaternary carbon centers by a base-catalyzed enantioselective aldol reaction and related reactions of trimethoxysilyl enol ethers

  摘要：

  The aldol reactions of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate were found to be powerful tools for the construction of quaternary asymmetric carbon centers. The stereoselectivities were greatly affected by the presence of water. Trimethoxysilyl enol ether derived from a cyclic ketone, such as cyclohexanone, was used as a substrate to obtain the anti-adduct preferentially under anhydrous conditions; by contrast, the syn-adduct was preferentially obtained under aqueous conditions with high stereoselectivity. The aldol-Tishchenko reaction of a trimethoxysilyl enol ether derived from acyclic ketones proceeded to give monoacyl 1,3-diol derivatives in high enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.096
• 作为产物：
  描述：

  2-甲基-3,4-二氢-2H-1-萘酮 、 trimethoxysilyl triflate 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以64%的产率得到2-methyl-1-(trimethoxysilyloxy)-3,4-dihydronaphthalene
  参考文献：
  名称：

  Construction of quaternary carbon centers by a base-catalyzed enantioselective aldol reaction and related reactions of trimethoxysilyl enol ethers

  摘要：

  The aldol reactions of trimethoxysilyl enol ethers catalyzed by lithium binaphtholate were found to be powerful tools for the construction of quaternary asymmetric carbon centers. The stereoselectivities were greatly affected by the presence of water. Trimethoxysilyl enol ether derived from a cyclic ketone, such as cyclohexanone, was used as a substrate to obtain the anti-adduct preferentially under anhydrous conditions; by contrast, the syn-adduct was preferentially obtained under aqueous conditions with high stereoselectivity. The aldol-Tishchenko reaction of a trimethoxysilyl enol ether derived from acyclic ketones proceeded to give monoacyl 1,3-diol derivatives in high enantioselectivities. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.096