(trimethylsilyl)methanesulfinyl chloride | 85532-03-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 亚磺酸及其衍生物
• 英文名称: (trimethylsilyl)methanesulfinyl chloride
• 英文别名: Trimethylsilylmethanesulfinyl chloride
• CAS: 85532-03-2
• 化学式: C₄H₁₁ClOSSi
• 分子量: 170.735
• InChiKey: DQSXEUXANRGPDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.77
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (trimethylsilyl)methanesulfinyl chloride 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以91%的产率得到trans-2,3-bis(trimethylsilyl)thiirane 1-oxide
  参考文献：
  名称：

  Gas-phase determination of the geometric requirements of the silicon .beta.-effect. Photoelectron and Penning ionization electron spectroscopic study of silylthiiranes and -oxiranes. Synthesis and chemistry of trans-2,3-bis(trimethylsilyl)thiirane

  摘要：

  DOI：

  10.1021/ja00222a037
• 作为产物：
  描述：

  (三甲基甲硅烷基)甲基硫代乙酸酯 在 氯 作用下， 以 乙酸酐 为溶剂， 以72%的产率得到(trimethylsilyl)methanesulfinyl chloride
  参考文献：
  名称：

  The chemistry of sulfines. 13. 2-Thiabicyclo[2.2.1]hept-5-ene and its S-oxides and 3-alkyl derivatives: sulfine and sulfene cyclopentadiene Diels-Alder adducts. Conversion of the cyclopentadiene-sulfine adducts into 2-oxa-3-thiabicyclo[3.3.0]oct-7-enes, novel bicyclic sultenes

  摘要：

  DOI：

  10.1021/jo00381a020

文献信息

• The chemistry of sulfines. 9. A novel synthesis of α-chloroalkyl alkanethiosulfonate esters
  作者：Eric Block、Ali A. Bazzi

  DOI：10.1016/s0040-4039(00)85656-7

  日期：1982.1

  Sulfines react with sulfinyl chlorides giving α-chloroalkyl alkanethiosulfonate esters and with thionyl chloride giving α-chloroalkanesulfenyl chlorides, both in good yields.

  硫与亚磺酰氯反应生成α-氯烷基链烷硫基磺酸酯，与亚硫酰氯反应生成α-氯链烷磺基氯化物，两者均收率良好。
• <i>Allium</i> Chemistry:  Microwave Spectroscopic Identification, Mechanism of Formation, Synthesis, and Reactions of (<i>E</i>,<i>Z</i>)-Propanethial <i>S</i>-Oxide, the Lachrymatory Factor of the Onion (<i>Allium cepa</i>)
  作者：Eric Block、Jennifer Z. Gillies、Charles W. Gillies、Ali A. Bazzi、David Putman、Larry K. Revelle、Dongyi Wang、Xing Zhang

  DOI：10.1021/ja960722j

  日期：1996.1.1

  Flow pyrolysis of 2-methyl-2-propyl 1'-propenyl sulfoxide (9b) affords a 98:2 mixture of (Z)- and (E)-propanethial S-oxide ((Z)- and (E)-5b), both characterized by Fourier transform microwave (FT-MW) spectroscopy, Sulfines (Z)- and (E)-5b are also identified by FT-MW in chopped onion volatiles and by NMR spectroscopy in onion extracts. Similarly, flow pyrolysis of 2-methyl-2-propyl vinyl sulfoxide (9c) affords (Z)- and (E)-isomers of ethanethial S-oxide (5a), identified by FT-MW methods. Pyrolysis in the presence of D2O affords (Z)-5a-d(1) and (Z)-5a-d(2) from 99 and (Z)-5b-d(1) from 9b; (Z)-5b-d(1) is also produced when an onion is homogenized in D2O. Pyrolysis of 9c with ethyl propiolate gives ethyl (E)-3-(vinylsulfinyl)acrylate (10). Neat 59 at 100 degrees C gives acetaldehyde. On standing, 5b dimerizes to trans-3,3-diethyl-1,2-dithietane 1,1-dioxide (12a); Me(3)SiCH=S+-O- (5f) undergoes an analogous dimerization. Compound 5b shows moderate potency as an anticarcinogen in inducing the enzyme quinone reductase.
• Synthesis of methanethial s-oxide (sulfine) and alkanethial s,s-dioxides by fluorodesilylation. Stereochemistry of their cyclopentadiene diels-alder adducts
  作者：Eric Block、Alan Wall

  DOI：10.1016/s0040-4039(00)99062-2

  日期：1985.1
• BLOCK, E.;BAZZI, A. A., TETRAHEDRON LETT., 1982, 23, N 44, 4569-4572
  作者：BLOCK, E.、BAZZI, A. A.

  DOI：——

  日期：——
• BLOCK, E.;WALL, A., TETRAHEDRON LETT., 1985, 26, N 11, 1425-1428
  作者：BLOCK, E.、WALL, A.

  DOI：——

  日期：——