2-trimethylsilyl-1,3-dithiolane | 358366-66-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: 2-trimethylsilyl-1,3-dithiolane
• 英文别名: 1,3-dithiolan-2-yl(trimethyl)silane
• CAS: 358366-66-2
• 化学式: C₆H₁₄S₂Si
• 分子量: 178.395
• InChiKey: PIWJUEQNICHGDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.67
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-噻吩甲醛 、 2-trimethylsilyl-1,3-dithiolane 在 四丁基氟化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以83%的产率得到1,3-Dithiolan-2-yl(thiophen-2-yl)methanol
  参考文献：
  名称：

  2-Trimethylsilyl-1,3-dithiolane as a masked dithiolane anion

  摘要：

  2-Trimethylsilyl-1,3 -dithiolane, easily obtainable through transthioacetalization of corresponding silylated acetals, can be efficiently reacted, under fluoride-ion catalysis, with different organic electrophiles, leading to a general and mild functionalization protocol. This reactivity discloses the ability of compound 3 to act as a masked dithiolane anion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00771-7
• 作为产物：
  描述：

  1,2-乙二硫醇 、 [Butoxy(methoxy)methyl]-trimethylsilane 在 三氟化硼乙醚 作用下， 以88%的产率得到2-trimethylsilyl-1,3-dithiolane
  参考文献：
  名称：

  2-Trimethylsilyl-1,3-dithiolane as a masked dithiolane anion

  摘要：

  2-Trimethylsilyl-1,3 -dithiolane, easily obtainable through transthioacetalization of corresponding silylated acetals, can be efficiently reacted, under fluoride-ion catalysis, with different organic electrophiles, leading to a general and mild functionalization protocol. This reactivity discloses the ability of compound 3 to act as a masked dithiolane anion. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00771-7

文献信息

• Tetrabutylammonium phenoxide induced reaction of silyl nucleophiles
  作者：Antonella Capperucci、Caterina Tiberi、Salvatore Pollicino、Alessandro Degl’Innocenti

  DOI：10.1016/j.tetlet.2009.03.167

  日期：2009.6

  promoted by catalytic amounts of tetrabutylammonium phenoxide (PhONn–Bu4), leading to a convenient access to functionalized dithiolanes. PhONn–Bu4 proved effective also in promoting reactions of silylated sulfides such as PhSTMS and HMDST as well as silylated selenides such as PhSeTMS and HMDSS toward epoxides. The present reactivity is also observed on using ILs as reaction media.

  与亲电甲硅烷基二硫的反应可以通过催化量的四丁基酚盐（PHON可以有效地促进Ñ -Bu 4），从而导致对官能化二硫的便利访问。PHON Ñ -Bu 4证明在促进甲硅烷基化的硫化物反应，如PhSTMS和HMDST以及甲硅烷基化硒化物如PhSeTMS和HMDSS朝向环氧化物也是有效的。当使用IL作为反应介质时，也观察到了当前的反应性。
• General access to a novel class of silyl heterocycles
  作者：A. Degl’Innocenti、A. Capperucci、I. Malesci、M. Acciai、G. Castagnoli

  DOI：10.1007/s10593-006-0280-2

  日期：2006.12
• STREET, LESLIE J.;BAKER, RAYMOND;BOOK, TRACEY;KNEEN, CLARE O.;MACLEOD, AN+, J. MED. CHEM., 33,(1990) N0, C. 2690-2697
  作者：STREET, LESLIE J.、BAKER, RAYMOND、BOOK, TRACEY、KNEEN, CLARE O.、MACLEOD, AN+

  DOI：——

  日期：——
• 2-Trimethylsilyl-1,3-dithiolane as a masked dithiolane anion
  作者：Alessandro Degl'Innocenti、Antonella Capperucci、Tiziano Nocentini

  DOI：10.1016/s0040-4039(01)00771-7

  日期：2001.7

  2-Trimethylsilyl-1,3 -dithiolane, easily obtainable through transthioacetalization of corresponding silylated acetals, can be efficiently reacted, under fluoride-ion catalysis, with different organic electrophiles, leading to a general and mild functionalization protocol. This reactivity discloses the ability of compound 3 to act as a masked dithiolane anion. (C) 2001 Elsevier Science Ltd. All rights reserved.