1-Methyl-3-(propane-2-sulfinyl)-benzene | 84321-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-Methyl-3-(propane-2-sulfinyl)-benzene
• 英文别名: 1-Methyl-3-(propane-2-sulfinyl)benzene；1-methyl-3-propan-2-ylsulfinylbenzene
• CAS: 84321-31-3
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: HXFHXQKIPWQSNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  1-Methyl-3-(propane-2-sulfinyl)-benzene 在 N-溴代丁二酰亚胺(NBS) 、 3-巯基丙酸 作用下， 以 乙腈 为溶剂， 反应 3.33h， 以89%的产率得到异丙基m-甲苯基硫醚
  参考文献：
  名称：

  N-Bromosuccinimideand Iodine Catalyzed Highly Efficient Deoxygenation ofSulfoxides to Thioethers Using 3-Mercaptopropionic Acid under Mild ReactionConditions

  摘要：

  多种烷基和芳基亚磺酸酯已成功使用3-巯基丙酸作为还原剂，并在室温下以MeCN为溶剂，加入少量的NBS或I2（5-10摩尔%）进行脱氧反应。在所描述的反应条件下，酸敏感底物如缩醛在经过几个小时后仍保持不变。

  DOI：

  10.1055/s-2003-40981
• 作为产物：
  描述：

  异丙基m-甲苯基硫醚 在 (SiO₂-O₃SiCH₂CH₂CH₂NH₃⁺)2WO₄^2- 双氧水 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到1-Methyl-3-(propane-2-sulfinyl)-benzene
  参考文献：
  名称：

  Selective Oxidation of Sulfides to Sulfoxides Using 30% Hydrogen Peroxide Catalyzed with a Recoverable Silica-Based Tungstate Interphase Catalyst

  摘要：

  Various types of aromatic and aliphatic sulfides are selectively oxidized to sulfoxides and sulfones in good to excellent yields using 30% H2O2 in the presence of catalytic amounts of a novel recoverable silica-based tungstate interphase catalyst at room temperature. The catalyst can be recovered and reused for at least eight reaction cycles under the described reaction conditions without considerable loss of reactivity.

  DOI：

  10.1021/ol047635d

文献信息

• Rapid, Efficient and Chemoselective Deoxygenation of Sulfoxides to Thioethers­ Using NaBH₄/I₂
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1055/s-2003-37349

  日期：——

  Sodium borohydride in the presence of iodine in anhydrous THF converts a range of structurally different sulfoxides to their thioethers in excellent yields. It has been found that chemoselective deoxygenation of sulfoxides can be achieved in the presence of other reducible functional groups such as esters, nitriles and double bonds.

  无水四氟呋喃中，碘存在下的氢化钠能够将一系列结构不同的亚砜高效转化为其硫醚。研究发现，在存在其他可还原功能团（如酯、腈和双键）时，可以实现亚砜的化学选择性去氧化。
• Rhodium-catalyzed enantioselective C–H alkynylation of sulfoxides in diverse patterns: desymmetrization, kinetic resolution, and parallel kinetic resolution
  作者：Lingheng Kong、Yun Zou、Xiao-Xi Li、Xue-Peng Zhang、Xingwei Li

  DOI：10.1039/d2sc05310a

  日期：——

  Rhodium-catalyzed enantioselective C–H alkynylation of achiral and racemic sulfoxides is disclosed with alkynyl bromide as the alkynylating reagent. A wide range of chiral sulfoxides have been constructed in good yield and excellent enantioselectivity (up to 99% ee, s-factor up to > 500) via desymmetrization, kinetic resolution, and parallel kinetic resolution under mild reaction conditions. The high

  公开了用炔基溴作为炔基化试剂的铑催化的非手性和外消旋亚砜的对映选择性 C-H 炔基化。在温和的反应条件下，通过去对称化、动力学拆分和平行动力学拆分，以良好的产率和出色的对映选择性（高达 99% ee， s因子高达 > 500）构建了多种手性亚砜。手性环戊二烯基铑（III) 催化剂与手性甲酰胺添加剂配对。在 C-H 键断裂过程中，手性催化剂、亚砜和手性羧酸酰胺之间的相互作用提供了不对称诱导，这通过 DFT 计算得到了验证。手性甲酰胺作为促进 C-H 活化的碱基，并在 C-H 裂解过程中提供额外的手性环境。
• Oxidation By Manganese Dioxide (mno₂) Catalysed With H₂SO₄/silica gel. Efficient solvent-Free Oxdation Of Thioethers To Their Corresponding Sulfoxides
  作者：H. Firouzabadi、M. Abbasi

  DOI：10.1080/00397919908086128

  日期：1999.5

  H2SO4 mixed with silica gel (1:2) by weight produces a white powder which is an effective catalyst for the oxidation of thioethers to their corresponding sulfoxide by MnO2 under solvent-free conditions.
• Enantioselective inclusion of chiral alkyl aryl sulfoxides in a supramolecular helical channel consisting of an enantiopure 1,2-amino alcohol and an achiral carboxylic acid
  作者：Yuka Kobayashi、Soetrisno、Koichi Kodama、Kazuhiko Saigo

  DOI：10.1016/j.tetasy.2007.11.041

  日期：2008.2

  The enantio selective clathrate formation of alkyl aryl sulfoxides 4 was achieved with dissymmetric one-dimensional helical channels created in two-component hosts consisting of (1R,2S)-2-amino-1,2-diphenylethanol 1 and an achiral carboxylic acid, p-tert-butylbenzoic acid 2, or 2-anthraquinonecarboxylic acid 3. X-ray crystallographic analyses showed that the host framework (1R,2S)-1.3 in the single crystal of a clathrate with methyl p-methylphenyl sulfoxide 4n [(1R,2S)-1.3.4n (single)] maintained a supramolecular helical array as those of the solvent-included single crystals (1R,2S)-1.3-EtOH(single) and (1R,2S)-1-3-H2O.THF(single), while the guest 4n molecules were highly disordered. Moreover, the X-ray powder diffraction pattern of (1R,2S)-1-3-4n(clathrate) obtained through the clathrate formation demonstrated that the molecular arrangements of (1R,2S)-1, 3, and 4n were not the same as those which appeared in (1R,2S)-1.3.4n(single); the channel was enlarged. These results are consistently explained by assuming the dynamic motion of the framework (1R,2S)-1-3 to achieve widely applicable clathrate formation. (c) 2007 Elsevier Ltd. All rights reserved.
• TRIMETHYLCHLOROSILANE (TMCS) CATALYZED EFFICIENT REDUCTION OF SULFOXIDES TO THIOETHERS USING 3-MERCAPTOPROPIONIC ACID UNDER MILD REACTION CONDITIONS
  作者：Babak Karimi、Daryoush Zareyee

  DOI：10.1080/10426500490257050

  日期：2004.1

  A variety of alkyl and aryl sulfoxides were successfully deoxygenated using 3-mercaptopropionic acid as reducing agent and a catalytic amount of trimethylchlorosilane (10-20 mol%) in CH3CN at ambient temperature.