3,5-bis(trimethylsilylethynyl)benzyl alcohol | 929192-60-9

• 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: 3,5-bis(trimethylsilylethynyl)benzyl alcohol
• 英文别名: 3,5-bis(trimethylsilylethynyl)benzalcohol；[3,5-Bis(2-trimethylsilylethynyl)phenyl]methanol；[3,5-bis(2-trimethylsilylethynyl)phenyl]methanol
• CAS: 929192-60-9
• 化学式: C₁₇H₂₄OSi₂
• 分子量: 300.548
• InChiKey: CISVWGFXRCMMJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,5-bis(trimethylsilylethynyl)benzyl alcohol 在 1-甲基吡咯烷 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 生成 3,5-bis((1,3,3-trimethylspiro[indoline-2,3'-naphtho[2,1-b][1,4]oxazine]-5-yl)ethynyl)phenylmethanol
  参考文献：
  名称：

  Synthesis, characterization, and solvent-independent photochromism of spironaphthooxazine dimers

  摘要：

  Specifically angled, conjugated spiroindolinonaphthooxazine dimers (SNOD) have been synthesized. The photochromic reactions of two types of SNOD were studied under continuous UV irradiation in solvents of different polarity. Comparison of these results with the single unit provides the examination of the specific effect of substituents on their photochromic properties and relaxation kinetics. The photomerocyanine isomers showed positive solvatochromism, supporting the premise for a less polar quinoidal structure. The thermal closing rate at 25 degrees C ranged from 0.2 to 1.6 s(-1) depending on the compound and solvent. Photochromism of these new compounds showed little dependency on solvent polarity and stable cyclability. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jphotochem.2011.11.011
• 作为产物：
  描述：

  3,5-二溴苯甲醇 、 三甲基乙炔基硅 在 copper(l) iodide 作用下， 生成 3,5-bis(trimethylsilylethynyl)benzyl alcohol
  参考文献：
  名称：

  通过Ir催化双（二芳基乙烯基氧化膦）的双不对称加氢合成手性1,3-双（1-（二芳基磷酰基）乙基）-苯

  摘要：

  通过相应的双（二芳基乙烯基膦氧化物）的双不对称氢化反应，以高非对映异构体比例和优异的ee值制备了一类手性1,3-双（二芳基膦基乙基）苯，它们是合成PCP型手性钳位配体的关键中间体。 ）底物使用SpinPhox / Ir（I）络合物作为催化剂。氢化产物5a容易地转化成具有高对映体过量的相应的硼烷保护的手性PCP型钳形配体7a，说明了向光学活性手性PCP钳型配体的可行合成路线。

  DOI：

  10.1007/s11426-014-5134-7

文献信息

• Designing dendritic frameworks using versatile building blocks suitable for CuI-catalyzed alkyne azide ‘click’ chemistry
  作者：Rami Hourani、Anjali Sharma、Ashok Kakkar

  DOI：10.1016/j.tetlet.2010.05.061

  日期：2010.7

  Synthesis of molecular building blocks that incorporate azide and alkyne-terminated functionalities suitable for Cu-I-catalyzed cycloaddition between alkynes and azides is reported. Their utility in constructing dendritic frameworks with 4, 6, or 12 peripheral acetylene groups using either the convergent or divergent methodology, and their functionalization with desirable end groups are demonstrated. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis, characterization, and solvent-independent photochromism of spironaphthooxazine dimers
  作者：Davita L. Watkins、Tomoko Fujiwara

  DOI：10.1016/j.jphotochem.2011.11.011

  日期：2012.1

  Specifically angled, conjugated spiroindolinonaphthooxazine dimers (SNOD) have been synthesized. The photochromic reactions of two types of SNOD were studied under continuous UV irradiation in solvents of different polarity. Comparison of these results with the single unit provides the examination of the specific effect of substituents on their photochromic properties and relaxation kinetics. The photomerocyanine isomers showed positive solvatochromism, supporting the premise for a less polar quinoidal structure. The thermal closing rate at 25 degrees C ranged from 0.2 to 1.6 s(-1) depending on the compound and solvent. Photochromism of these new compounds showed little dependency on solvent polarity and stable cyclability. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis of chiral 1,3-bis(1-(diarylphosphoryl)ethyl)-benzenes via Ir-catalyzed double asymmetric hydrogenation of bis(diarylvinylphosphine oxides)
  作者：Xu Liu、ZhaoBin Han、Zheng Wang、KuiLing Ding

  DOI：10.1007/s11426-014-5134-7

  日期：2014.8

  A class of chiral 1,3-bis(diarylphosphinoethyl)benzenes, which are key intermediates for the synthesis of PCP-type chiral pincer ligands, were prepared in high diastereomeric ratios and excellent ee values via double asymmetric hydrogenation of the corresponding bis(diarylvinylphosphine oxide) substrates using a SpinPhox/Ir(I) complex as the catalyst. The hydrogenation product 5a was readily transformed

  通过相应的双（二芳基乙烯基膦氧化物）的双不对称氢化反应，以高非对映异构体比例和优异的ee值制备了一类手性1,3-双（二芳基膦基乙基）苯，它们是合成PCP型手性钳位配体的关键中间体。 ）底物使用SpinPhox / Ir（I）络合物作为催化剂。氢化产物5a容易地转化成具有高对映体过量的相应的硼烷保护的手性PCP型钳形配体7a，说明了向光学活性手性PCP钳型配体的可行合成路线。