(Z)-2,2-dimethylpropanethial S-oxide | 74635-31-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代羰基化合物
• 英文名称: (Z)-2,2-dimethylpropanethial S-oxide
• 英文别名: (E)-2,2-dimethylpropanethial S-oxide；2,2-Dimethyl-1-sulfinylpropane
• CAS: 74635-31-7；74635-32-8；344240-11-5
• 化学式: C₅H₁₀OS
• 分子量: 118.2
• InChiKey: PTPANUXKBRGOCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  7
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-1,3-丁二烯 、 (Z)-2,2-dimethylpropanethial S-oxide 生成 (1R,2R)-2-tert-butyl-4,5-dimethyl-3,6-dihydro-2H-thiopyran 1-oxide
  参考文献：
  名称：

  BARBARO, G.;BATTAGLIA, A.;GIORGIANNI, P.;BONINI, B. F.;MACCAGNANI, G.;ZAN+, J. ORG. CHEM., 56,(1991) N, C. 2512-2518

  摘要：

  DOI：
• 作为产物：
  描述：

  neopentyl phenacyl sulfide 在 2,3-二甲基-1,3-丁二烯 、 间氯过氧苯甲酸 作用下， 以 氘代氯仿 、 苯 为溶剂， 反应 4.0h， 生成 (Z)-2,2-dimethylpropanethial S-oxide
  参考文献：
  名称：

  单体硫代新戊醛的表征

  摘要：

  合成 a partir de la neopentylthio-2 acetophenone。Reactive de ce thioaldehyde vis-a-vis-a-vis de phenyl-lithium, 丁基-lithium, acide chloro-3 perbenzoique, et (phenyl-3 亚丙基三苯基) 正膦

  DOI：

  10.1021/ja00271a030

文献信息

• 2,2-Dimethylpropanethial: a long-lived aliphatic thioaldehyde
  作者：E. Vedejs、D. A. Perry

  DOI：10.1021/ja00344a061

  日期：1983.3
• <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.
• Formation of .alpha.-disulfoxides, sulfinic anhydrides, and sulfines during the m-chloroperoxybenzoic acid oxidation of symmetrical S-alkyl alkanethiosulfinates
  作者：Fillmore Freeman、Christos N. Angeletakis

  DOI：10.1021/ja00350a049

  日期：1983.6
• Thioaldehyde S-oxide (monosubstituted sulfines) from thioacylsilane S-oxides. Synthesis and fluorine- and acid-induced Z/E isomerization. 2
  作者：G. Barbaro、Arturo Battaglia、P. Giorgianni、B. F. Bonini、G. Maccagnani、P. Zani

  DOI：10.1021/jo00299a012

  日期：1990.6
• Thermal and Lewis acid induced cycloaddition of thioaldehyde S-oxides (monosubstituted sulfines) to dienes. 3
  作者：G. Barbaro、Arturo Battaglia、P. Giorgianni、B. F. Bonini、G. Maccagnani、P. Zani

  DOI：10.1021/jo00007a045

  日期：1991.3

  The stereochemical course of the 1,4-cycloaddition of thioaldehyde S-oxides (monosubstituted sulfines) to 2,3-dimethylbuta-1,3-diene, buta-1,3-diene, and cis- and trans-penta-1,3-diene was investigated. Unexpectedly, the reactions of buta-1,3-diene and 2,3-dimethylbuta-1,3-diene with Z-monoaryl sulfines afforded cis/trans mixtures of the corresponding dihydrothiopyran S-oxides, in which the relative amounts of the two isomers depended upon the initial diene/sulfine ratio. A Z to E isomerization of the dienophiles during the cycloaddition was responsible. On the other hand, Z/E mixtures of aliphatic tert-butyl sulfine gave, with 2,3-dimethylbuta-1,3-diene, only the corresponding trans cycloadduct. Catalysis of the reaction by Lewis acids, heretofore largely unexplored, was also investigated.