Diisopropylsulfoxylat | 3359-71-5

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机含氧阴离子化合物
• 英文名称: Diisopropylsulfoxylat
• 英文别名: 2-({[(Propan-2-yl)oxy]sulfanyl}oxy)propane；2-propan-2-yloxysulfanyloxypropane
• CAS: 3359-71-5
• 化学式: C₆H₁₄O₂S
• 分子量: 150.242
• InChiKey: SEIFYNNOMSTCRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2915900090

反应信息

• 作为反应物：
  描述：

  Diisopropylsulfoxylat 在 二甲基二环氧乙烷 作用下， 以 氘代氯仿 为溶剂， 反应 0.05h， 以95%的产率得到亚硫酸二异丙酯
  参考文献：
  名称：

  Reaction of α-Peroxy Lactones with C, N, P, and S Nucleophiles:  Adduct Formation and Nucleophile Oxidation by Nucleophilic Attack at and Biphilic Insertion into the Peroxide Bond

  摘要：

  The reactions of the alpha-peroxy lactones 1 with a variety of carbon, nitrogen, phosphorus, and sulfur nucleophiles yield, on S(N)2 attack at the more electrophilic alkoxy oxygen of the peroxide bond, diverse addition and oxygen transfer products, together with the catalytic Grob-type fragmentation. The nature of the nucleophile determines the fate of the open-chain intermediate I. Thus, protic nucleophiles such as primary and secondary amines and thiols lead to the second intermediate I' through proton shift subsequent to the S(N)2 step, while nonprotic amines and sulfides, as well as diazoalkanes, lead to oxidation products or to the cycloadducts 10-15. Trivalent phosphorus nucleophiles such as phosphines and phosphites and diisopropyl sulfoxylate prefer biphilic insertion, as documented by the fact that the nucleophilicity rather than the steric demand of these reagents controls their reactivity. The labile adducts undergo a variety of transformations to the final stable products. For protic nucleophiles, the amine adducts 5 and 6 are sufficiently persistent for isolation, whereas the sulfenic esters formed by thiol addition are further oxidized to the sulfinic esters 7 and 8 or react with excess thiol to the corresponding disulfides. For aprotic nucleophiles, the dipolar intermediates I decompose into acetone and CO2 with regeneration of the nucleophile (Grob-type fragmentation), as seen for DABCO and pyridine N-oxide, or they extrude the alpha-lactone to afford the oxygen transfer product. The corresponding ketones, pyridine N-oxide, sulfoxides, and sulfones are obtained by this route from diazoalkanes, pyridine, sulfides and sulfoxides. Additionally, the diazoalkane intermediates I also cyclize to the cycloadducts 10-12. The thermally labile phosphorus adducts 13-15, which were observed by low-temperature NMR spectroscopy, decompose to the alpha-lactone and the phosphorus oxides. Analogously, diisopropyl sulfite is obtained from the sulfoxylate adduct. As for the fate of the alpha-lactones (the reduction products of the alpha-peroxy lactones), the dimethyl derivative either oligomerizes to the oligoester 2a or is trapped by methanol as the alpha-methoxy acid 4a, while the spiroadamantyl alpha-lactone decarbonylates to adamantanone.

  DOI：

  10.1021/jo962039l
• 作为产物：
  描述：

  异丙醇 在 二氯化硫 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 Diisopropylsulfoxylat
  参考文献：
  名称：

  Organic Esters of Bivalent Sulfur. III. Sulfoxylates

  摘要：

  DOI：

  10.1021/jo01019a046

文献信息

• Mikolajczyk, Marian; Kielbasinski, Piotr; Bujnicki, Bogdan, Phosphorus and Sulfur and the Related Elements, 1985, vol. 25, p. 85 - 90
  作者：Mikolajczyk, Marian、Kielbasinski, Piotr、Bujnicki, Bogdan、Wenschuh, Eberhard、Kuehne, Ulrich

  DOI：——

  日期：——
• Synthesis and vibrational spectra of new bis(alkoxysulfane)-dichloropalladium(II) complexes and X-ray structural analysis of [PdCl2{S(OPri)2}2]
  作者：Ralf Steudel、Monika Kustos、Heinar Schmidt、Eberhard Wenschuh、Mathias Kersten、Andrea Wloszczynski

  DOI：10.1039/dt9940002509

  日期：——

  Reactions of L = (Pr(i)O)2S, (PrnO)2S, (MeO)(C4H8NO)S (C4H8NO = morpholino), (MeO) (C5H10N)S (C5H10N = piperidino) or (MeO)PhS with [PdCl2(NCPh)2] in toluene gave five complexes of type [PdCl2L2] (yields 40-79%). An X-ray structural analysis of the air-stable, monoclinic crystals of [PdCl2S(OPe)2}2] showed the sulfur atoms to be cis-planar co-ordinated. The two co-ordinated dialkoxysulfane ligands are rotational isomers with differing SO torsional angles (+79 and 84-degrees for ligand 1, -106 and +82-degrees for 2). The S-0 bond lengths are in the range 1.586-1.611 angstrom. The infrared and Raman spectra of the five [PdCl2L2] complexes demonstrate that the rule of mutual exclusion is not obeyed, indicating a cis rather than a trans co-ordination in each case.
• Wenschuh, Eberhard; Kersten, Mathias, Phosphorus, Sulfur and Silicon and the Related Elements, 1994, vol. 91, # 1-4, p. 205 - 212
  作者：Wenschuh, Eberhard、Kersten, Mathias

  DOI：——

  日期：——
• Wenschuh,E. et al., Zeitschrift fur Chemie, 1978, vol. 18, p. 379 - 380
  作者：Wenschuh,E. et al.

  DOI：——

  日期：——
• Eine neue Synthese von Alkansulfinsäure-estern durch Reaktion von Sulfoxylsäure-estern mit Alkyljodiden
  作者：Eberhard WENSCHUH、Reinhard FAHSL、Renate HÖHNE

  DOI：10.1055/s-1976-24227

  日期：——