Trimethyl-(2-methyl-1-methylsulfanyl-propenyloxy)-silane | 77078-44-5

• 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: Trimethyl-(2-methyl-1-methylsulfanyl-propenyloxy)-silane
• 英文别名: Trimethyl-(2-methyl-1-methylsulfanylprop-1-enoxy)silane
• CAS: 77078-44-5
• 化学式: C₈H₁₈OSSi
• 分子量: 190.382
• InChiKey: PCIKXRLZMVNOQT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Trimethyl-(2-methyl-1-methylsulfanyl-propenyloxy)-silane 、 三甲基氯硅烷 在 sodium 作用下， 以 苯 为溶剂， 反应 4.5h， 以81%的产率得到2-Methyl-1-trimethylsilanyl-1-trimethylsilanyloxy-propene
  参考文献：
  名称：

  Conversion of Carbon-Sulfur Linkages into Carbon–Silicon OnesviaReductive Silylation. Preparation of Silyl Enol Ethers of Acyltrimethylsilanes

  摘要：

  在三甲基氯硅烷存在下，用钠或钾钠合金处理可诱导硫代羧酸 S 酯硅基烯醇醚的碳硫键发生还原性裂解，并以高产率制备出相应的酰基三甲基硅烷硅基烯醇醚。

  DOI：

  10.1246/bcsj.53.2634
• 作为产物：
  描述：

  三甲基氯硅烷 、 S-甲基2-甲基硫代丙酸酯 在 lithium diisopropyl amide 作用下， 生成 Trimethyl-(2-methyl-1-methylsulfanyl-propenyloxy)-silane
  参考文献：
  名称：

  Conversion of Carbon-Sulfur Linkages into Carbon–Silicon OnesviaReductive Silylation. Preparation of Silyl Enol Ethers of Acyltrimethylsilanes

  摘要：

  在三甲基氯硅烷存在下，用钠或钾钠合金处理可诱导硫代羧酸 S 酯硅基烯醇醚的碳硫键发生还原性裂解，并以高产率制备出相应的酰基三甲基硅烷硅基烯醇醚。

  DOI：

  10.1246/bcsj.53.2634

文献信息

• Notable Sulfur Atom Effects on the Regio- and Stereoselective Formation of Oxetanes in Paternò−Büchi Photocycloaddition of Aromatic Aldehydes with Silyl O,S-Ketene Acetals
  作者：Manabu Abe、Kiyotada Fujimoto、Masatomo Nojima

  DOI：10.1021/ja993997i

  日期：2000.5.1

  Paterno-Buchi photocycloaddition of silyl O,S-ketene acetals (SKA) 1 and aromatic aldehydes 2 was investigated in detail. The photoreaction of aldehydes 2a-d with beta,beta-dimethyl-O,S-SKA 1a-e has been found to give, regio- (ca. 70/30 to 90/10) and stereoselectively (ca. 70/30 to 90/10), trans-3-siloxyoxetanes 3 independent upon the aldehyde, the substituents SR1 and SiR3, and reaction medium (solvent and salts). The triplet 2-oxatetramethylene 1,4-diradical T-1,4-DR is reasonably proposed as a common intermediate. The regioselectivity is rationalized by (1) the relative stability of 1,4-diradicals and (2) the relative nucleophilicity of sp(2)-carbons in O,S-SKA. The trans-selectivity is explained by the sulfur atom effects in O,S-SKA 1, which control the approach direction of the electrophilic oxygen of triplet n pi* aldehydes to the nucleophilic alkene. The fast ISC process of the triplet 1-alkylthio-1-siloxy-2-oxatetramethylene 1,4-diradical T-1,4-DR in competition with the bond rotation has been proposed. The substrate-dependent formation of 3fb from E- or Z-1f supports the hypothesis. The S-directed regio- and diastereoselectivity are found for the first time in the present study.
• KUWAJINA I.; MORI A.; KATO M., BULL. CHEM. SOC. JAP., 1980, 53, NO 9, 2634-2638
  作者：KUWAJINA I.、 MORI A.、 KATO M.

  DOI：——

  日期：——
• Conversion of Carbon-Sulfur Linkages into Carbon–Silicon Ones<i>via</i>Reductive Silylation. Preparation of Silyl Enol Ethers of Acyltrimethylsilanes
  作者：Isao Kuwajima、Akio Mori、Masahiro Kato

  DOI：10.1246/bcsj.53.2634

  日期：1980.9

  Reductive cleavage of carbon–sulfur linkages of silyl enol ethers of thiocarboxylic S-esters can be induced by treatment with sodium or potassium–sodium alloy in the presence of chlorotrimethylsilane, and the corresponding silyl enol ethers of acyltrimethylsilanes can be prepared in high yields.

  在三甲基氯硅烷存在下，用钠或钾钠合金处理可诱导硫代羧酸 S 酯硅基烯醇醚的碳硫键发生还原性裂解，并以高产率制备出相应的酰基三甲基硅烷硅基烯醇醚。