S-nitroso-2-propanethiol | 69165-81-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: S-nitroso-2-propanethiol
• 英文别名: Isopropylthionitrit；thionitrous acid S-isopropyl ester；2-nitrososulfanyl-propane；2-Nitrososulfanylpropane
• CAS: 69165-81-7
• 化学式: C₃H₇NOS
• 分子量: 105.161
• InChiKey: YHNQHKCHRDOVOY-UHFFFAOYSA-N

物化性质

• 沸点：
  115.7±23.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  S-nitroso-2-propanethiol 在 air 作用下， 以 氯仿 为溶剂， 反应 0.17h， 以95%的产率得到异丙基二硫醚
  参考文献：
  名称：

  聚乙烯吡咯烷酮（PVP–N 2 O 4）上负载的四氧化二氮：一种新的硫醇亚硝化和偶联剂，以及一种硫化物和二硫化物的选择性氧化剂

  摘要：

  将气态N 2 O 4固定在聚乙烯吡咯烷酮上，得到稳定的聚合试剂。硫醇转化为小号在使用这个新的亚硝化剂-nitrosothiols（thionitrites）ñ -己烷或氯仿3在10℃下。使用该试剂，硫醇也被转化为其相应的二硫化物。在室温下，也可以通过该试剂将硫化物选择性氧化为亚砜，将二硫化物选择性氧化为硫代磺酸盐。通过使用过量的试剂，在室温下也从硫醇选择性地一锅合成硫代磺酸盐。

  DOI：

  10.1016/s0040-4020(02)00390-3
• 作为产物：
  描述：

  异丙硫醇 在 dinitrogen tetroxide impregnated on activated charcoal 作用下， 以 二氯甲烷 为溶剂， 生成 S-nitroso-2-propanethiol
  参考文献：
  名称：

  四氧化二氮浸渍木炭（N2O4/木炭）：胺、酰胺、尿素和硫醇的选择性硝化

  摘要：

  摘要 胺、酰胺和尿素的有效 N-亚硝化以及硫醇的 S-亚硝化在室温下用四氧化二氮浸渍在 CH2Cl2 中的活性炭（N2O4/木炭）上进行。观察到二烷基胺、N-烷基酰胺和 N-烷基脲的 N-亚硝化具有高选择性。三烷基胺的脱烷基化和 N-亚硝化也由该试剂进行。

  DOI：

  10.1081/scc-200057999

文献信息

• Synthesis, characterization, and protonation of octaethylporphyrin osmium nitrosyl complexes containing axial thiolate ligands - X-ray structures of an alkyl thionitrite (RSNO) and its (OEP)Os(NO)(SR) addition product
  作者：Jonghyuk Lee、Geun-Bae Yi、Douglas R Powell、Masood A Khan、George B Richter-Addo

  DOI：10.1139/v00-168

  日期：2001.5.1

  The (OEP)Os(NO)(SR) compounds (R = Me, Et, i-Pr, t-Bu) have been prepared in 33-48% isolated yields by the formal trans-addition of the precursor alkyl thionitrites (RSNO) across the metal center in (OEP)Os(CO). The nitrosyl thiolate compounds have been characterized by IR,¹H NMR, and UV-vis spectroscopy, and by FAB mass spectrometry. Their IR spectra display bands in the 1751-1755 cm^-1(KBr) range, which is indicative of terminal N-bound NO ligands in this class of compounds. The thiolate-thiol (OEP)Os(NO)(SCH₂CH₂SH) complex has been prepared in 70% isolated yield from the reaction of (OEP)Os(NO)(O-i-C₅H₁₁) with ethane-1,2-dithiol. Nitrosation of the free -SH group in (OEP)Os(NO)(SCH₂CH₂SH) with t-BuONO, followed by reaction with (TTP)Ru(CO) gave [(OEP)Os(NO)](µ-SCH₂CH₂S-S,S')[Ru(NO)(TTP)] in 70% yield by¹H NMR spectroscopy. The (OEP)Os(NO)(SCR'₂CH₂NHC(O)Me) compounds have also been prepared either by an alkoxide-thiolate exchange reaction (for R' = H) or by RSNO addition to (OEP)Os(CO) (for R' = Me). The solid-state molecular structures of the precursor RSNO thionitrite (for R' = Me) and the metalloderivative have been determined by single-crystal X-ray crystallography. Protonation of these (OEP)Os(NO)(SCR'₂CH₂NHC(O)Me) complexes gave the amide-bound [(OEP)Os(NO)(O=C(Me)NHCH₂CR'₂SH)]BF₄derivatives. The latter cationic compounds were also obtained by the sequential reaction of (OEP)Os(CO) with nitrosonium tetrafluoroborate, followed by addition of the amide-thiol reagent. Key words: thionitrite, nitrosothiol, porphyrin, X-ray structure, nitric oxide, osmium.

  (OEP)Os(NO)(SR)化合物（其中R = 甲基，乙基，异丙基，叔丁基）通过前体烷基硫亚硝酸酯（RSNO）在（OEP）Os(CO)金属中心上的形式转加反应，以33-48%的分离收率制备。这些亚硝基硫醇酸盐化合物已通过红外光谱，¹H核磁共振，紫外-可见光谱和FAB质谱进行表征。它们的红外光谱显示在1751-1755 cm^-1（KBr）范围内的吸收峰，表明这类化合物中存在末端N-配位的NO配体。通过（OEP）Os(NO)(O-i-C₅H₁₁)与乙烷-1,2-二硫醇反应，已以70%的分离收率制备了硫醇-硫醇（OEP）Os(NO)(SCH₂CH₂SH)配合物。通过¹H核磁共振光谱，用t-BuONO硝化（OEP）Os(NO)(SCH₂CH₂SH)中的自由-SH基团，然后与（TTP）Ru(CO)反应，得到了[(OEP)Os(NO)](µ-SCH₂CH₂S-S,S')[Ru(NO)(TTP)]，收率为70%。还通过烷氧基-硫醇酸盐交换反应（对于R' = H）或RSNO加成到（OEP）Os(CO)（对于R' = Me）制备了（OEP）Os(NO)(SCR'₂CH₂NHC(O)Me)化合物。通过单晶X射线衍射确定了前体RSNO硫亚硝酸酯（对于R' = Me）和金属衍生物的固态分子结构。这些（OEP）Os(NO)(SCR'₂CH₂NHC(O)Me)配合物的质子化产生了酰胺配位的[(OEP)Os(NO)(O=C(Me)NHCH₂CR'₂SH)]BF₄衍生物。后者阳离子化合物也可通过（OEP）Os(CO)与四氟硼酸亚硝酰盐的顺序反应，然后加入酰胺-硫醇试剂获得。关键词：硫亚硝酸酯，亚硝基硫醇，卟啉，X射线结构，一氧化氮，锇。
• Barnett, D.Jonathan; Rios, Ana; Williams, D. Lyn H., Journal of the Chemical Society. Perkin transactions II, 1995, # 7, p. 1279 - 1282
  作者：Barnett, D.Jonathan、Rios, Ana、Williams, D. Lyn H.

  DOI：——

  日期：——
• Reactions of isopropylthio radical with oxygen, nitrogen dioxide, and nitric oxide at 296 K
  作者：Graham Black、Leonard E. Jusinski、Roger Patrick

  DOI：10.1021/j100316a026

  日期：1988.3
• Dinitrogen tetroxide supported on polyvinylpyrrolidone (PVP–N2O4): a new nitrosating and coupling agent for thiols and a selective oxidant for sulfides and disulfides
  作者：Nasser Iranpoor、Habib Firouzabadi、Ali-Reza Pourali

  DOI：10.1016/s0040-4020(02)00390-3

  日期：2002.6

  S-nitrosothiols (thionitrites) using this new nitrosating agent in n-hexane or CHCl3 at 10°C. With this reagent, thiols were also converted into their corresponding disulfides. Selective oxidation of sulfides to sulfoxides and disulfides to thiosulfonates can also be achieved by this reagent at room temperature. By using an excess of the reagent, the selective one-pot synthesis of thiosulfonates from thiols

  将气态N 2 O 4固定在聚乙烯吡咯烷酮上，得到稳定的聚合试剂。硫醇转化为小号在使用这个新的亚硝化剂-nitrosothiols（thionitrites）ñ -己烷或氯仿3在10℃下。使用该试剂，硫醇也被转化为其相应的二硫化物。在室温下，也可以通过该试剂将硫化物选择性氧化为亚砜，将二硫化物选择性氧化为硫代磺酸盐。通过使用过量的试剂，在室温下也从硫醇选择性地一锅合成硫代磺酸盐。
• Dinitrogen Tetroxide–Impregnated Charcoal (N₂O₄/Charcoal): Selective Nitrosation of Amines, Amides, Ureas, and Thiols
  作者：Nasser Iranpoor、Habib Firouzabadi、Ali Reza Pourali

  DOI：10.1081/scc-200057999

  日期：2005.6

  Abstract Efficient N‐nitrosation of amines, amides, and ureas, and also S‐nitrosation of thiols were performed with dinitrogen tetroxide impregnated on activated charcoal (N2O4/charcoal) in CH2Cl2 at room temperature. High selectivity was observed for N‐nitrosation of dialkyl amines, N‐alkylamides and N‐alkylureas. Dealkylation and N‐nitrosation of trialkylamines were also performed by this reagent

  摘要 胺、酰胺和尿素的有效 N-亚硝化以及硫醇的 S-亚硝化在室温下用四氧化二氮浸渍在 CH2Cl2 中的活性炭（N2O4/木炭）上进行。观察到二烷基胺、N-烷基酰胺和 N-烷基脲的 N-亚硝化具有高选择性。三烷基胺的脱烷基化和 N-亚硝化也由该试剂进行。