(R)-1-(isopropylsulfinyl)-3-methylbenzene | 84413-70-7

• 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: (R)-1-(isopropylsulfinyl)-3-methylbenzene
• 英文别名: (+)-r-Isopropyl m-tolyl sulfoxide；1-methyl-3-[(R)-propan-2-ylsulfinyl]benzene
• CAS: 84413-70-7
• 化学式: C₁₀H₁₄OS
• 分子量: 182.287
• InChiKey: HXFHXQKIPWQSNJ-GFCCVEGCSA-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

• 作为产物：
  描述：

  异丙基m-甲苯基硫醚 在 manganese(II) triflate 、 N1,N2-Bis(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)phenyl)benzene-1,2-diamine 、 双氧水 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以92%的产率得到(R)-1-(isopropylsulfinyl)-3-methylbenzene
  参考文献：
  名称：

  卟啉启发的锰配合物的不对称氧化催化：广泛的底物范围的高度对映选择性的硫氧化。

  摘要：

  成功开发出了首个真正有前景的，受卟啉启发的锰催化的不对称硫氧化方法，该方法使用过氧化氢，可快速氧化（0.5–1.0 h），高产率地以优异的对映选择性（高达> 99％ee）对多种硫化物进行氧化。 。

  DOI：

  10.1021/ol402612x

文献信息

• 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。
• 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.
• Asymmetric Oxidation Catalysis by a Porphyrin-Inspired Manganese Complex: Highly Enantioselective Sulfoxidation with a Wide Substrate Scope
  作者：Wen Dai、Jun Li、Bo Chen、Guosong Li、Ying Lv、Lianyue Wang、Shuang Gao

  DOI：10.1021/ol402612x

  日期：2013.11.15

  The first genuinely promising porphyrin-inspired manganese-catalyzed asymmetric sulfoxidation method using hydrogen peroxide has been successfully developed, allowing for rapidly oxidizing (0.5–1.0 h) a wide variety of sulfides in high yields with excellent enantioselectivities (up to >99% ee).

  成功开发出了首个真正有前景的，受卟啉启发的锰催化的不对称硫氧化方法，该方法使用过氧化氢，可快速氧化（0.5–1.0 h），高产率地以优异的对映选择性（高达> 99％ee）对多种硫化物进行氧化。 。