3,3'-[1,1,3,3-四甲基丙烷二硅氧烷-1,3-二基]二(1-丙硫醇) | 18001-52-0

• 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
• 中文名称: 3,3'-[1,1,3,3-四甲基丙烷二硅氧烷-1,3-二基]二(1-丙硫醇)
• 英文名称: 1,1,3,3-Tetramethyl-1,3-bis-(3-mercapto-propyl)-disiloxan
• 英文别名: {me2(n-pr-3-SH)Si}2O；4,4,6,6-tetramethyl-5-oxa-4,6-disila-nonane-1,9-dithiol；1,3-Bis-(3-mercapto-propyl)-1,1,3,3-tetramethyl-disiloxan；4,4,6,6-Tetramethyl-5-oxa-4,6-disila-nonan-1,9-dithiol；3-[[Dimethyl(3-sulfanylpropyl)silyl]oxy-dimethylsilyl]propane-1-thiol
• CAS: 18001-52-0
• 化学式: C₁₀H₂₆OS₂Si₂
• 分子量: 282.619
• InChiKey: IAVCFZPUOKBIHK-UHFFFAOYSA-N

物化性质

• 沸点：
  282.7±25.0 °C(Predicted)
• 密度：
  0.943±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.05
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  11.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为产物：
  描述：

  1,3-二烯丙基四甲基二硅烷 在 sodium hydroxide 作用下， 生成 3,3'-[1,1,3,3-四甲基丙烷二硅氧烷-1,3-二基]二(1-丙硫醇)
  参考文献：
  名称：

  含硅的聚亚烷基硫醚。十一

  摘要：

  发现六亚甲基二硫醇和二烯丙基二甲基硅烷乳液聚合的最佳 pH 值在 3.0 至 4.0 的范围内。使用本体聚合、溶液聚合和乳液聚合技术制备了多种含硅的聚亚烷基硫醚。所有含硅的聚亚烷基硫醚都是非常“发粘”的重油性材料。

  DOI：

  10.1002/pol.1952.120090104

文献信息

• The sila-Pummerer rearrangement of 3,3-dimethyl-3-silathiane S-oxide
  作者：Svetlana V. Kirpichenko、Elena N. Suslova、Alexandr I. Albanov、Bagrat A. Shainyan

  DOI：10.1016/s0040-4039(98)80054-3

  日期：1999.1

  The thermal conversion of sulfoxide 1 into the O-silylated cyclic O,S-acetal (2) is the first example of the sila-Pummerer rearrangement of cyclic organosilicon sulfoxides leading to ring expansion. The kinetics of the rearrangement are studied and thermodynamic parameters are determined. The results are in compliance with mechanism involving a pentacoordinated silicon atom.

  亚砜1到O-甲硅烷基化的环状O，S-乙缩醛（2）的热转化是环状有机硅亚砜的sila-Pummerer重排导致环膨胀的第一个例子。研究了重排动力学，并确定了热力学参数。结果符合涉及五配位硅原子的机理。
• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: Si: MVol.C, 93, page 253 - 257
  作者：

  DOI：——

  日期：——
• Marvel, C. S.; Cripps, H. N., 1952, vol. 9, p. 53 - 60
  作者：Marvel, C. S.、Cripps, H. N.

  DOI：——

  日期：——
• Comparative reactivity of substituted 1,3-and 1,4-thiasilinane S-oxides in the sila-Pummerer rearrangement and inversion of the thiocarbonyl group
  作者：E. N. Suslova、I. A. Ushakov、B. A. Shainyan

  DOI：10.1134/s1070363207020119

  日期：2007.2

  The thermal sila-Pummerer rearrangement of diastereomeric 2,3,3-trimethyl-1,3-thiasilinane S-oxides was studied. Introduction of the methyl group in the 2 position of 3,3-trimethyl-3-thiasilinane S-oxide slows down the rearrangement. When heated in CCl4, the trans isomer (2-Me-eq, SOeq) converts into the cis isomer (2-Me-eq, SOax) which rapidly rearranges into 2,2,7-trimethyl-1,6,2-oxathiasilepane. On the contrary, the isomeric 2,4,4-trimethyl-1,4-thiasilinane S-oxide is thermally stable up to 160 degrees C in DMSO. The inversion at the sulfur atom in 2,3,3-trimethyl-1,3-thiasilinane S-oxides and 2,4,4-trimethyl-1,4-thiasilinane S-oxides under the action of triethyloxonium tetrafluoroborate was studied. The trans isomer of 2,3,3-trimethyl-1.3-thiasilinane S-oxide (2-Me-eq, SOeq) forms with Et3O+BF4- a salt which decomposes in two ways. The first involves recovery of the starting sulfoxide due to SN2 substitution at the carbon atom of the ethoxy group, and the second, convertion into the cis isomer (2-Meeq, SOax) which rearranges into 2,2,7-trimethyl-1,6,2-oxathiasilepane. Under the same conditions, the cis isomer of 2,3,3-trimethyl-1,3-thiasilinane S-oxide (2-Me-eq: SOeq) decomposes to form siloxanes. traiis-2,4,4-Trimethyl-4-thiasilinane S-oxide (2-Me-eq, SOeq) under the action of Et3O+BF4- convers into the cis isomer (2-Me-eq, SOax). The B3LYP/6-311G(d,p) theoretical analysis showed that the thermal inversion at the sulfur atom in the compounds studied has a high energy barrier.