(5-bromopentyl)chlorodimethylsilane | 119914-32-8

• 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: (5-bromopentyl)chlorodimethylsilane
• 英文别名: 5-Bromopentyl-chloro-dimethylsilane
• CAS: 119914-32-8
• 化学式: C₇H₁₆BrClSi
• 分子量: 243.647
• InChiKey: DKZZTWJRLGELBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  10
• 可旋转键数：
  5
• 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：

  (5-bromopentyl)chlorodimethylsilane 在 dihydrogen hexachloroplatinate lithium aluminium tetrahydride 作用下， 以 乙醚 、 异丙醇 、 甲苯 为溶剂， 反应 1.5h， 生成 (5-bromopentyl)dimethyl(3-(1,8-naphthalimido)propyl)silane
  参考文献：
  名称：

  Synthesis and pharmacological characterization of new silicon-based W84-type allosteric modulators for ligand binding to muscarinic M2 receptors

  摘要：

  The silicon-based allosteric modulators of ligand binding to muscarinic acetylcholine receptors [R-1-(CH2)(3)-SiMe2-(CH2)(5)- NMe2-(CH2)(3)-R-1]Br (3), [R-2-(CH2)(3)-SiMe2 (CH2)(5)-NMe2-(CH2)(3)-R-2]Br (4), [R-1-(CH2)(3)-SiMe2-(CH2)(3)-NMe2-(CH2)(3)- R-2]Br (5), and [R-2-(CH2)(3)-SiMe2- (CH2)(5)-NMe2-(CH2)(3)-R-1]Br (6) (R-1 = phthalimido; R-2 = 1,8-naphthalimido) were sythesized, starting from chlorodimethylsilane. Compounds 3-6 were studied for their allosteric interaction at porcine heart muscarinic M-2 receptors. They inhibited the dissociation of the orthosteric ligand [H-3]N-methylscopolamine ([H-3]NMS) with similar potency; compounds 4 and 6 yielded steep concentration-effect curves. All compounds enhanced [H-3]NMS equilibrium binding, but with different efficacies. The effect of 4 on [H-3]NMS binding was studied at cloned M-1-M-5 receptor subtypes. Compound 4 did not affect [H-3]NMS equilibrium binding at M-1, M-3, M-4, and M-5 receptors, thus representing an M-2-selective allosteric enhancer of [H-3]NMS binding. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00553-9
• 作为产物：
  描述：

  二甲基一氯硅烷 、 5-溴-1-戊烯 在 dihydrogen hexachloroplatinate 作用下， 以 异丙醇 、 甲苯 为溶剂， 以77%的产率得到(5-bromopentyl)chlorodimethylsilane
  参考文献：
  名称：

  Synthesis and pharmacological characterization of new silicon-based W84-type allosteric modulators for ligand binding to muscarinic M2 receptors

  摘要：

  The silicon-based allosteric modulators of ligand binding to muscarinic acetylcholine receptors [R-1-(CH2)(3)-SiMe2-(CH2)(5)- NMe2-(CH2)(3)-R-1]Br (3), [R-2-(CH2)(3)-SiMe2 (CH2)(5)-NMe2-(CH2)(3)-R-2]Br (4), [R-1-(CH2)(3)-SiMe2-(CH2)(3)-NMe2-(CH2)(3)- R-2]Br (5), and [R-2-(CH2)(3)-SiMe2- (CH2)(5)-NMe2-(CH2)(3)-R-1]Br (6) (R-1 = phthalimido; R-2 = 1,8-naphthalimido) were sythesized, starting from chlorodimethylsilane. Compounds 3-6 were studied for their allosteric interaction at porcine heart muscarinic M-2 receptors. They inhibited the dissociation of the orthosteric ligand [H-3]N-methylscopolamine ([H-3]NMS) with similar potency; compounds 4 and 6 yielded steep concentration-effect curves. All compounds enhanced [H-3]NMS equilibrium binding, but with different efficacies. The effect of 4 on [H-3]NMS binding was studied at cloned M-1-M-5 receptor subtypes. Compound 4 did not affect [H-3]NMS equilibrium binding at M-1, M-3, M-4, and M-5 receptors, thus representing an M-2-selective allosteric enhancer of [H-3]NMS binding. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/s0022-328x(03)00553-9

文献信息

• Electrochemical synthesis of cyclic alkylsilanes
  作者：V. Jouikov、V. Krasnov

  DOI：10.1016/0022-328x(95)05528-w

  日期：1995.8

  RnSiCl4−n(n = 0, 2) was shown to afford heterocyclic silicon compounds in good yield (up to 91%). In contrast to non-electrochemical methods of synthesis of silacycloalkanes, based on the ring closure of terminal unsaturated compounds, the electrochemical route does not produce α-methylated byproducts and the heterocycle formation occurs quite selectively. The yield of cyclic organosilicon compounds goes

  在式R n SiCl 4- n（n的多氯硅烷存在下，脂肪族α，ω-二溴化物的电化学还原= 0，2）被证明可以提供高收率的杂环硅化合物（高达91％）。与合成非硅烷基环烷烃的非电化学方法相反，基于末端不饱和化合物的闭环，电化学途径不会产生α-甲基化副产物，并且杂环的形成非常有选择性。环状有机硅化合物的收率在1,1,1-二甲基-1-硅环戊烷（91％）处达到最大值，而在1,1-二甲基-1-硅环丁烷（18％）和1,1-二甲基-1-苯环己烷中的产率下降硅环庚烷（57％）。尽管存在许多可能的反应路径，并且由于硅的高官能度而形成聚合物的可能性很高，但通过电化学过程形成5-silaspiro [4,4]壬烷的反应具有很高的选择性。电化学闭环的较高选择性被认为是由于在单甲硅烷基化中间体中CHal键不可逆还原过程中电极的定向作用所致。讨论了该过程的可能机制。