2,2-双(三甲基甲硅烷基氧基)-1,1-联萘 | 156568-04-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2,2-双(三甲基甲硅烷基氧基)-1,1-联萘
• 英文名称: 2,2'-bis(trimethylsiloxy)-1,1'-bi-2-naphthyl
• 英文别名: (R)-(+)-di-O-TMS-binaphthol；[[1,1'-Binaphthalene]-2,2'-diylbis(oxy)]bis(trimethylsilane)；trimethyl-[1-(2-trimethylsilyloxynaphthalen-1-yl)naphthalen-2-yl]oxysilane
• CAS: 156568-04-6；163615-28-9；167900-98-3
• 化学式: C₂₆H₃₀O₂Si₂
• 分子量: 430.694
• InChiKey: HICHTPUMVRXTTH-UHFFFAOYSA-N

物化性质

• 沸点：
  471.5±40.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.09
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-双(三甲基甲硅烷基氧基)-1,1-联萘 在 三溴化磷 作用下， 以37%的产率得到2,2-二溴-1,1-联萘
  参考文献：
  名称：

  A strongly binding, helically chiral ligand system

  摘要：

  描述了包含两个菲咯啉单元的两个螺旋手性配体系统的合成、表征和结合特性，其氮在一个系统中大致呈四面体排列，并且可能在第二个系统中以这种方式排列。

  DOI：

  10.1039/c39930001323
• 作为产物：
  描述：

  六甲基二硅氮烷 、 S-1,1'-联-2-萘酚 在 三氟甲磺酸三甲基硅酯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以86%的产率得到2,2-双(三甲基甲硅烷基氧基)-1,1-联萘
  参考文献：
  名称：

  Chirochromism-Photochromism by Epimerization: Search for a Liquid Crystal Phototrigger

  摘要：

  A new class of photochromic reactions was investigated as a possible trigger for phase transitions in liquid crystals. Chirochromic compounds have two chiral units. One unit is fixed, and the other can be switched with light. A series of diastereomeric compounds based on ketals and acetals of 1,1'-bi-2-naphthol was prepared. In some cases, the absorption spectra of the diastereomers are measurably different. The ketals do not undergo efficient photoepimerization, apparently because the activation barrier for atropisomerism in their triplet state has increased. However, certain of the acetal derivatives do photoepimerize and are chirochromic. These compounds may be developed into triggers.

  DOI：

  10.1021/ja00090a033

文献信息

• A facile route to germanium(IV) binaphthoxide complexes: crystal structure of a chiral resolved germanium(IV) binaphthoxide
  作者：Miguel A. Léal、Arnold L. Rheingold、Charles S. Weinert

  DOI：10.1016/j.mencom.2022.01.005

  日期：2022.1

  A method for the facile synthesis of chiral germanium(IV) binaphthoxide complexes from the corresponding binaphthols and an organogermanium trichloride has been developed, which allows these unusual types of compounds to be synthesized in high yields. The crystal structure of one such complex, (S)-[GeO2C20H10(SiMe3)2-3,3'}Cl}Ph}], has been determined.

  已经开发了一种从相应的联萘酚和三氯化有机锗轻松合成手性联萘锗 (IV) 配合物的方法，该方法可以高收率地合成这些不寻常类型的化合物。已经确定了一种这样的配合物 ( S )-[GeO2C20H10(SiMe3)2-3,3'}Cl}Ph}] 的晶体结构。
• Chiral BINOL-based borate counterions: from cautionary tale on anion stability to enantioselective Cu-catalyzed cyclopropanation
  作者：Anthony Labelle、Bruce A. Arndtsen

  DOI：10.1039/d2cc05924j

  日期：——

  Studies on a new type of chiral BINOL-based boron counterion highlights its ability to rearrange under the reaction conditions to create a ligand that can be used in the copper-catalyzed cyclopropanation of alkenes.

  对一种新型手性BINOL基硼对离子的研究表明，它能够在反应条件下重排，生成可用于铜催化的烯烃环丙基化反应的配体。
• Chapuis, C.; Bauer, T.; Jezewski, A., Polish Journal of Chemistry, 1994, vol. 68, # 11, p. 2323 - 2332
  作者：Chapuis, C.、Bauer, T.、Jezewski, A.、Jurczak, J.

  DOI：——

  日期：——
• Chirochromism-Photochromism by Epimerization: Search for a Liquid Crystal Phototrigger
  作者：Mingbao Zhang、Gary B. Schuster

  DOI：10.1021/ja00090a033

  日期：1994.6

  A new class of photochromic reactions was investigated as a possible trigger for phase transitions in liquid crystals. Chirochromic compounds have two chiral units. One unit is fixed, and the other can be switched with light. A series of diastereomeric compounds based on ketals and acetals of 1,1'-bi-2-naphthol was prepared. In some cases, the absorption spectra of the diastereomers are measurably different. The ketals do not undergo efficient photoepimerization, apparently because the activation barrier for atropisomerism in their triplet state has increased. However, certain of the acetal derivatives do photoepimerize and are chirochromic. These compounds may be developed into triggers.
• A strongly binding, helically chiral ligand system
  作者：J. Kevin Judice、Steven J. Keipert、Donald J. Cram

  DOI：10.1039/c39930001323

  日期：——

  The syntheses, characterization and binding properties are described for two helically chiral ligand systems containing two phenanthroline units whose nitrogens are roughly tetrahedrally arranged in one system and potentially arrangeable that way in a second.

  描述了包含两个菲咯啉单元的两个螺旋手性配体系统的合成、表征和结合特性，其氮在一个系统中大致呈四面体排列，并且可能在第二个系统中以这种方式排列。