o-(tert-butyldimethylsilyl)anisole | 86998-00-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: o-(tert-butyldimethylsilyl)anisole
• 英文别名: 2-tert-butyldimethylsilylanisole；Tert-butyl-(2-methoxyphenyl)-dimethylsilane
• CAS: 86998-00-7
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: NFIMORGLIUIJRA-UHFFFAOYSA-N

物化性质

• 沸点：
  272.6±23.0 °C(Predicted)
• 密度：
  0.90±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.41
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 、 o-(tert-butyldimethylsilyl)anisole 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 反应 18.0h， 以50%的产率得到
  参考文献：
  名称：

  Chiral Modularn-Butyllithium Aggregates:nBuLi Complexes with Anisyl Fencholates

  摘要：

  Chiral enantiopure aggregates are formed spontaneously by mixing solutions of n-butyllithium with anisyl fenchols. X-ray crystal analyses reveal the structures of these aggregates with different ortho substituents in the anisyl moieties (X), X = H (1-H), SiMe3 (2-H), tBu (3-H) SiMe2(tBu) (4-H) and Me (5-H). While the complex of 1-BuLi shows a 3:1 composition, 2-BuLi. 3-BuLi and 4-BuLi yield 2,2 stoichiometries. The aggregate 5-BuLi crystallizes with a 2:4 composition and hence is a derivative of hexameric n-butyllithium, in which two trans-situated nBuLi molecules are substituted by lithium fencholate moieties. The variety in the synthesized chiral nBuLi aggregates demonstrates the high propensity of anisyl fencholates to chirally modify nBuLi. Variations in the modular ligand structures by alterations of the ortho-substituents (X) enable tunings of compositions and also of enantioselectivities in nBuLi additions to benzaldehyde.

  DOI：

  10.1002/1521-3765(20011015)7:20<4456::aid-chem4456>3.0.co;2-s
• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 2-methoxyphenyllithium 生成 o-(tert-butyldimethylsilyl)anisole
  参考文献：
  名称：

  Fukui, Mineo; Ikeda, Toshiya; Oishi, Takeshi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 2, p. 466 - 475

  摘要：

  DOI：

文献信息

• Fukui, Mineo; Ikeda, Toshiya; Oishi, Takeshi, Chemical and pharmaceutical bulletin, 1983, vol. 31, # 2, p. 466 - 475
  作者：Fukui, Mineo、Ikeda, Toshiya、Oishi, Takeshi

  DOI：——

  日期：——
• Chiral Modularn-Butyllithium Aggregates:nBuLi Complexes with Anisyl Fencholates
  作者：Bernd Goldfuss、Melanie Steigelmann、Frank Rominger、Heiko Urtel

  DOI：10.1002/1521-3765(20011015)7:20<4456::aid-chem4456>3.0.co;2-s

  日期：2001.10.15

  Chiral enantiopure aggregates are formed spontaneously by mixing solutions of n-butyllithium with anisyl fenchols. X-ray crystal analyses reveal the structures of these aggregates with different ortho substituents in the anisyl moieties (X), X = H (1-H), SiMe3 (2-H), tBu (3-H) SiMe2(tBu) (4-H) and Me (5-H). While the complex of 1-BuLi shows a 3:1 composition, 2-BuLi. 3-BuLi and 4-BuLi yield 2,2 stoichiometries. The aggregate 5-BuLi crystallizes with a 2:4 composition and hence is a derivative of hexameric n-butyllithium, in which two trans-situated nBuLi molecules are substituted by lithium fencholate moieties. The variety in the synthesized chiral nBuLi aggregates demonstrates the high propensity of anisyl fencholates to chirally modify nBuLi. Variations in the modular ligand structures by alterations of the ortho-substituents (X) enable tunings of compositions and also of enantioselectivities in nBuLi additions to benzaldehyde.