tert-Butyl-(4-[1,3]dithian-2-yl-butoxy)-dimethyl-silane | 115843-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二噻烷
• 英文名称: tert-Butyl-(4-[1,3]dithian-2-yl-butoxy)-dimethyl-silane
• 英文别名: tert-butyl-[4-(1,3-dithian-2-yl)butoxy]-dimethylsilane
• CAS: 115843-67-9
• 化学式: C₁₄H₃₀OS₂Si
• 分子量: 306.609
• InChiKey: PNTAFQVQNZBAMM-UHFFFAOYSA-N

物化性质

• 沸点：
  352.3±22.0 °C(Predicted)
• 密度：
  0.966±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  18.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-Butyl-(4-[1,3]dithian-2-yl-butoxy)-dimethyl-silane 在 四丁基氟化铵 、 叔丁基锂 、 mercury dichloride 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,3R,4R,6S)-4-chloro-3-methyl-2-((S)-1-methylpropyl)-1,7-dioxaspiro[5,5]undecane
  参考文献：
  名称：

  米尔贝霉素和阿维菌素螺缩醛的不对称合成

  摘要：

  Spiroacetals（16）和（29）已经从二甲基（合成小号） -苹果（9）通过其使用手性硼试剂，以控制立体化学会聚路由。

  DOI：

  10.1039/c39870001826
• 作为产物：
  描述：

  2-甲氧基四氢吡喃 在 咪唑 、 4-二甲氨基吡啶 、 三氟化硼乙醚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 tert-Butyl-(4-[1,3]dithian-2-yl-butoxy)-dimethyl-silane
  参考文献：
  名称：

  The acyl effect on intramolecular palladium-catalyzed trimethylenemethane cycloadditions

  摘要：

  Enhancing the generality of the intramolecular palladium-catalyzed [3 + 2] cycloaddition involving trimethylenemethane complexes as reactive intermediates is possible by incorporation of acyl substituents on the TMM unit. Such substituted TMM-PdL2 species greatly expand the scope such that bicyclo[3.3.0]octyl, bicyclo[4.3.0]nonyl, and bicyclo[5.3.0]decyl ring systems all can be created. Furthermore, the acyl-TMM chemistry permits incorporation of a bridgehead methyl substituent-the first example of a TMM-PdL2 cycloaddition in synthetically useful yields initiated by attack of a tertiary carbon in the first step to give a quaternary center. The requisite substrates are readily available using nucleophilic acylations via lithiated thioacetals. A general lynchpin strategy derives from bis(methylthio)methane onto which can be attached both the donor and acceptor partners of the cycloaddition. 2-((Trimethylsilyl)methyl)propenal serves as a convenient conjunctive reagent to introduce the donor partner. Alternatively 2-acyldithianes serve as a lynchpin to build substrates leading to bicycles bearing bridgehead substituents. In this case, 2-bromo-3-(trimethylsilyl)propene serves as a convenient conjunctive reagent to create the donor partner. The beneficial effect of acyl substitution derives from a combination of inhibiting side reactions derived from protodesilylation processes and facilitating the initial step of this nonconcerted cycloaddition. In addition to improving the generality of the intramolecular process, the ketone group that results in the product is a powerful functionality for further structural elaboration.

  DOI：

  10.1021/jo00028a052

文献信息

• A convergent synthesis of the C(11)–C(25) fragment of the aglycone of avermectin A2b
  作者：Eric Menager、Eric Merifield、Mark Smallridge、Eric J. Thomas

  DOI：10.1016/s0040-4020(97)00590-5

  日期：1997.7

  Oxidation of the mixture of products obtained by treatment of (S)-2-methylbutanal 8 with the E-but-2-enyldi-isopinocampheylborane prepared from (+)-pinene gave a mixture of homoallylic alcohols from which the major isomer 9 was isolated by chromatography. Oxidation with vanadylacetoacetate and tert-butyl hydroperoxide gave the epoxides 12 and 13, ratio 80 : 20. Following procedures developed in a synthesis of the model spiroacetal 19, 1,3-dithiane was alkylated, firstly using the epoxide 12, and then, after protection of the product 21 so obtained as its acetonide 23, using the epoxide 25, to give the 2,2-dialkylated 1,3-dithiane 25. Deprotection was accompanied by cyclisation to give the spiroacetal 28. Spiroacetal 29 was similarly prepared and taken through to the C(11)-C(25) fragment 38 of the aglycone of avermectin A(2b) 3. (C) 1997 Elsevier Science Ltd.
• MERIFIELD, ERIC;STEEL, PATRICK G.;THOMAS, ERIC J., J. CHEM. SOC. CHEM. COMMUN.,(1987) N 24, 1826-1828
  作者：MERIFIELD, ERIC、STEEL, PATRICK G.、THOMAS, ERIC J.

  DOI：——

  日期：——