chloromethyldioctylsilane | 53053-78-4

• 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: chloromethyldioctylsilane
• 英文别名: Chloro-methyl-dioctylsilane
• CAS: 53053-78-4
• 化学式: C₁₇H₃₇ClSi
• 分子量: 305.019
• InChiKey: WQAGHVKGINTQBT-UHFFFAOYSA-N

物化性质

• 沸点：
  350.4±11.0 °C(Predicted)
• 密度：
  0.856±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.52
• 重原子数：
  19
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  chloromethyldioctylsilane 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丙胺 、 三苯基膦 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 17.0h， 生成 1-ethynyl-4-[(methyldioctylsilyl)ethynyl]benzene
  参考文献：
  名称：

  Trialkylsilylethynyl-substituted triphenylenes and hexabenzocoronenes: highly soluble liquid crystalline materials and their hole transport abilities

  摘要：

  Four triphenylene (TP) and four hexa-peri-hexabenzocoronene (HBC) derivatives with trialkylsilylethynyl groups were prepared and characterized by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. All compounds were highly soluble in less-polar organic solvents and exhibited a columnar phase, Col(h) or Col(r) for the TPs, and Col(h) for the HBCs. The hole transport ability in the HBCs' columnar phase, 0.4-1.5x10(-3) cm(2) V-1 s(-1) at 40-180 degrees C, and its temperature dependence were determined by the time-of-flight method using a solution technique. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.071
• 作为产物：
  描述：

  1-溴辛烷 在 四氯化碳 、 magnesium 、 palladium dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 chloromethyldioctylsilane
  参考文献：
  名称：

  Trialkylsilylethynyl-substituted triphenylenes and hexabenzocoronenes: highly soluble liquid crystalline materials and their hole transport abilities

  摘要：

  Four triphenylene (TP) and four hexa-peri-hexabenzocoronene (HBC) derivatives with trialkylsilylethynyl groups were prepared and characterized by differential scanning calorimetry, polarizing optical microscopy, and X-ray diffraction measurements. All compounds were highly soluble in less-polar organic solvents and exhibited a columnar phase, Col(h) or Col(r) for the TPs, and Col(h) for the HBCs. The hole transport ability in the HBCs' columnar phase, 0.4-1.5x10(-3) cm(2) V-1 s(-1) at 40-180 degrees C, and its temperature dependence were determined by the time-of-flight method using a solution technique. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.071

文献信息

• A General and Selective Synthesis of Methylmonochlorosilanes from Di-, Tri-, and Tetrachlorosilanes
  作者：Yuki Naganawa、Kei Sakamoto、Yumiko Nakajima

  DOI：10.1021/acs.orglett.0c04175

  日期：2021.1.15

  Direct catalytic transformation of chlorosilanes into organosilicon compounds remains challenging due to difficulty in cleaving the strong Si–Cl bond(s). We herein report the palladium-catalyzed cross-coupling reaction of chlorosilanes with organoaluminum reagents. A combination of [Pd(C3H5)Cl]2 and DavePhos ligand catalyzed the selective methylation of various dichlorosilanes 1, trichlorosilanes 5

  由于难以裂解牢固的Si-Cl键，氯硅烷直接催化转化为有机硅化合物仍然具有挑战性。我们在本文中报道了氯硅烷与有机铝试剂的钯催化交叉偶联反应。[Pd（C 3 H 5）Cl] 2和DavePhos配体的组合催化了各种二氯硅烷1，三氯硅烷5和四氯硅烷6的选择性甲基化，得到了相应的一氯硅烷。
• Preparation of Tetraalkylsilanes from Trichloromethylsilane and Trioctylaluminum
  作者：Edward T. Sabourin、Anatoli Onopchenko

  DOI：10.1246/bcsj.62.3691

  日期：1989.11

  The synthesis of methyltrioctylsilane has been achieved in a single-step from commercially available trichloromethylsilane and trioctylaluminum. Co-products resulting from alkyl group redistribution are minimized by addition of sodium or lithium halides. Use of potassium or rubidium halides drastically changes the course of the reaction to produce methyldioctylsilane as the major product.

  利用市售的三氯甲基硅烷和三辛基铝，一步即可合成甲基三辛基硅烷。通过加入钠或锂卤化物，可将烷基重新分布产生的副产物降至最低。使用钾或铷卤化物会大大改变反应的过程，从而生成主要产品甲基二辛基硅烷。
• Synthesis of triorganylchlorosilanes by catalytic reaction of triorganylsilanes with chlorobenzene
  作者：Yu. I. Khudobin、N. A. Andreeva、N. P. Kharitonov、M. G. Voronkov

  DOI：10.1007/bf00923508

  日期：1974.4
• Andrianov,K.A. et al., Journal of general chemistry of the USSR, 1976, vol. 46, p. 2166 - 2168
  作者：Andrianov,K.A. et al.

  DOI：——

  日期：——
• Mass spectra of some high molecular weight tetra(alkyl)silanes
  作者：Anatoli Onopchenko、Edward T. Sabourin、David A. Danner

  DOI：10.1002/oms.1210200805

  日期：1985.8

  AbstractThe mass spectra of tetra(alkyl)silanes having one short and three long alkyl groups were recorded (C20C32). These silanes did not give molecular ions, and the dominant course of fragmentation involved the loss of alkyl groups, followed by elimination of alkenes. The loss of alkyl groups, followed by elimination of alkenes. The loss of alkyl groups followed the sequence iso‐Pr>Et, Pr,… C14H29» Me. With alkyl groups longer than hexyl, a rearrangement was observed in which n‐alkanes were eliminated from the base ion. When the alkyl group was hexyl, the alkane eliminated was methane; when the alkyl group was heptyl, ethane was expelled; with octyl, it was propane; and with decyl, n‐pentane was expelled. Deuterium labeling showed that at least two modes of rearrangement were occurring.