(R)-(2-methoxyphenyl)(methyl)phenylsilane | 1173908-74-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-(2-methoxyphenyl)(methyl)phenylsilane
• 英文别名: o-anisylmethylphenylsilane；(2-Methoxyphenyl)-methyl-phenylsilane；(2-methoxyphenyl)-methyl-phenylsilane
• CAS: 1173908-74-1
• 化学式: C₁₄H₁₆OSi
• 分子量: 228.366
• InChiKey: CWIHLAAMKPEFJV-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.67
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  tert-butyl N-(4-methoxyphenyl)-N-[(1S)-2-[(2-methoxyphenyl)-methyl-phenylsilyl]oxy-1-phenylethyl]carbamate 在 二异丁基氢化铝 作用下， 以 正己烷 、 二丁醚 为溶剂， 反应 48.0h， 以68%的产率得到(R)-(2-methoxyphenyl)(methyl)phenylsilane
  参考文献：
  名称：

  Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives

  摘要：

  Optically pure 1,3,2-oxazasilolidine derivatives were synthesized from a chiral 1,2-amino alcohol. These heterocyclic compounds containing a stereogenic silicon atom produced tertiary silanes with excellent optical purity through successive reactions with Grignard reagents and diisobutylaluminum hydride. Stereochemical course of the reactions of the oxazasilolidine at the chiral silicon atom was elucidated based on the absolute configurations of the products and the substrate which were determined by chiral HPLC and X-ray crystallographic analyses. (C) 2009 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2009.02.022

文献信息

• Access to Chiral Silicon Centers for Application to Circularly Polarized Luminescence Materials
  作者：Shinya Koga、Shuhei Ueki、Masaki Shimada、Ryoma Ishii、Yu Kurihara、Yoshinori Yamanoi、Junpei Yuasa、Tsuyoshi Kawai、Taka-aki Uchida、Munetaka Iwamura、Koichi Nozaki、Hiroshi Nishihara

  DOI：10.1021/acs.joc.7b00583

  日期：2017.6.16

  stepwise, one-pot procedure was used to transform the appropriate aryl iodide to the quaternary silane (22) with good yield and enantioselectivity. Among compounds synthesized in this work, four optically pure tertiary silanes (18–21) were selected to investigate the relationship between the structure and optical properties. Optically pure (S,S)-21 displayed the highest CPL emission with a high fluorescence

  开发了Pd-手性亚磷酰胺络合物催化的仲硅烷的不对称芳基化反应，用于低分子量圆偏振发光（CPL）材料。不对称芳基化用于各种手性叔硅烷（提供一个方便，高效合成法2 - 21，这是关键的中间体用于制备季硅中心）。使用逐步的一锅法将合适的芳基碘化物以良好的收率和对映选择性转化为季硅烷（22）。在这项工作中合成的化合物中，有四种光学纯的叔硅烷（18 – 21选择）以研究结构与光学性质之间的关系。光学纯的（S，S） - 21具有高荧光量子产率（显示最高CPL发射克LUM：0.008，Φ ˚F：0.42）。这种简单的分子设计为开发小型有机CPL染料提供了新的策略。
• Synthesis of optically active tertiary silanes via Pd-catalyzed enantioselective arylation of secondary silanes
  作者：Yu Kurihara、Michihiro Nishikawa、Yoshinori Yamanoi、Hiroshi Nishihara

  DOI：10.1039/c2cc36238d

  日期：——

  describe the development of an efficient enantioselective catalytic system that promotes the arylation of secondary silanes. Our method involves treatment of secondary silanes and aryl iodides with a Pd(2)(dba)(3)-asymmetric phosphoramidite ligand system to afford optically active tertiary silanes with good enantioselectivities.

  我们在本文中描述了促进仲硅烷的芳基化的有效对映选择性催化体系的发展。我们的方法涉及用Pd（2）（dba）（3）-不对称亚磷酰胺配体系统处理仲硅烷和芳基碘化物，以提供具有良好对映选择性的光学活性叔硅烷。
• Palladium-catalyzed Si–C bond-forming silylation of aryl iodides with hydrosilanes: an enhanced enantioselective synthesis of silicon-stereogenic silanes by desymmetrization
  作者：Li Chen、Jiang-Bo Huang、Zheng Xu、Zhan-Jiang Zheng、Ke-Fang Yang、Yu-Ming Cui、Jian Cao、Li-Wen Xu

  DOI：10.1039/c6ra12873d

  日期：——

  An enantioselective Pd-catalyzed silicon–carbon bond-forming silylation reaction of aryl iodides with hydrosilanes for the synthesis of silicon-stereogenic silanes has been developed, in which a systematic optimization of a TADDOL-derived monodentate phosphoramidite ligand set resulted in the identification of a new TADDOL-derived phosphoramidite ligand that accesses chiral silanes with moderate to

  开发了一种对映选择性的Pd催化的芳基碘化物与氢硅烷的硅碳键形成甲硅烷基化反应，用于合成硅立体异构的硅烷，其中系统优化了TADDOL衍生的单齿亚磷酰胺配体，从而确定了一种新的TADDOL衍生的亚磷酰胺配体，可在温和条件下以中等至良好的收率和对映选择性接近手性硅烷。
• Stereocontrolled synthesis of tertiary silanes via optically pure 1,3,2-oxazasilolidine derivatives
  作者：Natsuhisa Oka、Masahiko Nakamura、Naomi Soeda、Takeshi Wada

  DOI：10.1016/j.jorganchem.2009.02.022

  日期：2009.6

  Optically pure 1,3,2-oxazasilolidine derivatives were synthesized from a chiral 1,2-amino alcohol. These heterocyclic compounds containing a stereogenic silicon atom produced tertiary silanes with excellent optical purity through successive reactions with Grignard reagents and diisobutylaluminum hydride. Stereochemical course of the reactions of the oxazasilolidine at the chiral silicon atom was elucidated based on the absolute configurations of the products and the substrate which were determined by chiral HPLC and X-ray crystallographic analyses. (C) 2009 Elsevier B. V. All rights reserved.