chloromethyl(3-hydroxypropyl)methyl(phenyl)silane | 133511-55-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: chloromethyl(3-hydroxypropyl)methyl(phenyl)silane
• 英文别名: methylphenyl(chloromethyl)(3-hydroxypropyl)silane；chloromethyl(3-hydroxypropyl)methylphenylsilane；3-(Chloromethyl-methyl-phenylsilyl)propan-1-ol
• CAS: 133511-55-4
• 化学式: C₁₁H₁₇ClOSi
• 分子量: 228.794
• InChiKey: YHMDDFCBDJYVDZ-UHFFFAOYSA-N

物化性质

• 沸点：
  324.7±22.0 °C(Predicted)
• 密度：
  1.05±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  chloromethyl(3-hydroxypropyl)methyl(phenyl)silane 在 四氯化碳 、 三苯基膦 作用下， 反应 8.0h， 以47%的产率得到methylphenyl(chloromethyl)(3-chloropropyl)silane
  参考文献：
  名称：

  Synthesis and conformational analysis of 1,3-azasilinanes

  摘要：

  1-Isopropyl-3-methyl-3-phenyl-1,3-azasilinane 1 and 1-isopropyl-3,3-dimethyl-1,3-azasilinane 2 were synthesized and a detailed analysis of their NMR spectra, conformational equilibria and ring inversion processes is presented. Low temperature H-1/C-13 NMR spectroscopy, iteration of the H-1 NMR spectra and quantum chemical calculations showed slight predominance of the PheqMeax over the PhaxMeeq conformer of 1 at low temperature. The barrier for the chair to chair interconversion of both compounds was measured to be 8.25 kcal/mol. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.106
• 作为产物：
  描述：

  allyl(chloromethyl)methylphenylsilane 在 硼烷四氢呋喃络合物 、 双氧水 作用下， 以58%的产率得到chloromethyl(3-hydroxypropyl)methyl(phenyl)silane
  参考文献：
  名称：

  分子内亲核攻击硅诱导的α-卤代硅烷重排

  摘要：

  有机基团从硅向碳的迁移通过硅的醇盐的分子内攻击而促进。

  DOI：

  10.1016/s0040-4039(00)61765-3

文献信息

• Synthesis and Conformational Analysis of 3-Methyl-3-silatetrahydropyran by GED, FTIR, NMR, and Theoretical Calculations: Comparative Analysis of 1-Hetero-3-methyl-3-silacyclohexanes
  作者：Bagrat A. Shainyan、Svetlana V. Kirpichenko、Nina N. Chipanina、Larisa P. Oznobikhina、Erich Kleinpeter、Sergey A. Shlykov、Dmitriy Yu. Osadchiy

  DOI：10.1021/acs.joc.5b02355

  日期：2015.12.18

  1 was synthesized and its molecular structure and conformational behavior was studied by gas-phase electron diffraction (GED), FTIR, low temperature 1H and 13C NMR spectroscopy, and by theoretical calculations (DFT, MP2). Two conformers, 1-ax and 1-eq, were located on the potential energy surface. In the gas phase, a slight predominance of the axial conformer was determined, with the ratio 1-ax:1-eq

  合成了3-甲基-3-silatetrahydropyran 1，并通过气相电子衍射（GED），FTIR，低温1 H和13 C NMR光谱以及理论计算（DFT，MP2）研究了其分子结构和构象行为。两个构象子1-ax和1-eq位于势能表面上。在气相中，确定了轴向构象的轻微优势，比率为1-ax：1-eq = 54（9）：46（9）（来自GED）或53:47或61:39（来自IR） ）。在溶液中，在103ķLT NMR谱给出了比1-AX：1-当量= 35:65（-Δ ģ ° 103= 0.13 kcal / mol）。使用PCM连续谱模型或通过计算相应的溶剂-溶质配合物来模拟溶剂效果，使我们能够合理化实验观察到的在气相和溶液中3-甲基-3-silatetrahydropyran构象的相反构象优势。进行了1-杂-3-甲基-3-硅杂环己烷中杂原子对构象异构体的结构，立体电子相互作用和相对能的影响的比较分析。
• An efficient one-pot protocol for the synthesis of phenyl substituted 3-silatetrahydropyrans
  作者：Svetlana V. Kirpichenko、Bagrat A. Shainyan

  DOI：10.1016/j.tet.2014.12.037

  日期：2015.1

  A new facile and efficient one-pot procedure for the synthesis of 3-phenyl-3-silatetrahydropyrans with an easily functionalized Si-Ph bond was developed. The method is based on the intramolecular cyclization of chloromethyl(3-hydroxypropyl)phenylsilanes using the n-Bu4NBr/i-Pr2NEt combination. As an example of functionalization, the synthesis of the first 3-silatetrahydropyran with an exocyclic RO-Si bond is reported. (C) 2014 Elsevier Ltd. All rights reserved.
• Rearrangements of α-halosilanes induced by intramolecular nucleophilic attack at silicon
  作者：Paul F. Hudrlik、Yousef M. Abdallah、Anne M. Hudrlik

  DOI：10.1016/s0040-4039(00)61765-3

  日期：1992.11

  Migrations of organic groups from silicon to carbon are facilitated by intramolecular attack by alkoxide at silicon.

  有机基团从硅向碳的迁移通过硅的醇盐的分子内攻击而促进。
• Synthesis and conformational analysis of 1,3-azasilinanes
  作者：Bagrat A. Shainyan、Svetlana V. Kirpichenko、Erich Kleinpeter

  DOI：10.1016/j.tet.2012.05.106

  日期：2012.9

  1-Isopropyl-3-methyl-3-phenyl-1,3-azasilinane 1 and 1-isopropyl-3,3-dimethyl-1,3-azasilinane 2 were synthesized and a detailed analysis of their NMR spectra, conformational equilibria and ring inversion processes is presented. Low temperature H-1/C-13 NMR spectroscopy, iteration of the H-1 NMR spectra and quantum chemical calculations showed slight predominance of the PheqMeax over the PhaxMeeq conformer of 1 at low temperature. The barrier for the chair to chair interconversion of both compounds was measured to be 8.25 kcal/mol. (C) 2012 Elsevier Ltd. All rights reserved.