isopropyl-p-anisyl sulfoxide | 138723-23-6

• 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: isopropyl-p-anisyl sulfoxide
• 英文别名: Isopropyl-p-methoxyphenylsulfoxid；isopropyl (4-methoxyphenyl) sulfoxide；1-Methoxy-4-(propane-2-sulfinyl)benzene；1-methoxy-4-propan-2-ylsulfinylbenzene
• CAS: 138723-23-6；138723-24-7；7205-71-2
• 化学式: C₁₀H₁₄O₂S
• 分子量: 198.286
• InChiKey: KYCYKXQXFWNAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  isopropyl-p-anisyl sulfoxide 在 乙基溴化镁 、 异丙胺 作用下， 以66%的产率得到isopropenyl 4-methoxyphenyl sulfide
  参考文献：
  名称：

  Synthesis of 1-(1-Arylsulfanylalkyl)indoles and 2,2-Bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes by Acid-Catalyzed Reactions of Indoles with Aryl Vinyl Sulfides

  摘要：

  We report a facile synthesis of 1-(1-arylsulfanylalkyl)indoles and 2,2-bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes under mild conditions. Thus, treatment of 3-substituted indoles with aryl vinyl sulfides in dichloromethane at room temperature in the presence of a catalytic amount of (+/-)-camphor-10-sulfonic acid yields the former indole derivatives in moderate to fair yields. 3-Nonsubstituted indoles can be transformed into the latter indole derivatives in satisfactory yields on treatment with excess aryl vinyl sulfides in the presence of a catalytic amount of the acid under similar conditions.

  DOI：

  10.3987/com-09-11867
• 作为产物：
  描述：

  4-methoxyphenyl isopropyl sulfide 在 FeTPPSCl 咪唑 、 双氧水 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以78%的产率得到isopropyl-p-anisyl sulfoxide
  参考文献：
  名称：

  水溶性铁卟啉催化芳香族硫化物的氧化机理。

  摘要：

  在水溶性铁卟啉5,10,15催化的酸性（pH 3）水性介质中，H2O2氧化H2O2氧化了许多芳基硫化物，研究了氧原子转移-电子转移（ET）机理的二分法， 20-四苯基-21H，23H-卟啉-p，p′，p″，p″′-四磺酸氯化三铁（FeTPPSCl）。在这些反应条件下，铁-氧配合物卟啉自由基阳离子P +。Fe（IV）= O应该是活性氧化剂。当研究一系列对位X取代的苯基烷基硫化物（X = OCH3，CH3，H，Br，CN）的氧化时，相应的亚砜是唯一观察到的产物，反应收率和反应性几乎不受X的性质以及烷基的体积。使用H（2）18O或H（2）18O2进行的标记实验清楚地表明，亚砜中的氧原子仅来自氧化剂。此外，在苄基苯基硫醚的氧化中未观察到任何断裂产物，该自由基的阳离子预期会发生βCH和CS键的断裂。这些结果似乎表明氧原子直接从铁-氧配合物转移至硫化物。但是，硫代苯甲醚（H2O中的E度= 1.49 V

  DOI：

  10.1039/b209004j

文献信息

• Aryl Sulfoxides via Palladium-Catalyzed Arylation of Sulfenate Anions
  作者：Guillaume Maitro、Sophie Vogel、Guillaume Prestat、David Madec、Giovanni Poli

  DOI：10.1021/ol062315a

  日期：2006.12.1

  [Structure: see text] Palladium-catalyzed arylation of sulfenate anions generated from beta-sulfinyl esters can take place under biphasic conditions. This hitherto unknown reaction provides a simple, mild, and efficient route to aryl sulfoxides in good yields. The development of a new pseudo-domino type I procedure involving a sulfinylation followed by a Mirozoki-Heck coupling is also described.

  [结构：见正文]由β-亚磺酰基酯生成的亚硫酸根阴离子的钯催化芳基化反应可在两相条件下进行。迄今为止未知的反应提供了简单，温和且有效的途径，以高收率制备芳基亚砜。还描述了涉及亚磺酰基化然后进行Mirozoki-Heck偶联的新的假多米诺骨牌I型程序的开发。
• Desymmetrization of Prochiral Diaryl Sulfoxides by an Asymmetric Sulfoxide-Magnesium Exchange
  作者：Thomas Hampel、Simon Ruppenthal、Daniel Sälinger、Reinhard Brückner

  DOI：10.1002/chem.201103928

  日期：2012.3.12

  The first desymmetrizations of prochiral diaryl sulfoxides 1 by an asymmetric sulfoxide–magnesium exchange reaction are reported. The respective substrate (1), iPr2Mg, and the dilithium salt of (S)‐BINOL (which was prepared in situ) provided (S)‐configured aryl isopropyl sulfoxides 2 in up to 91 % yield and with up to 91 % ee. (S)‐BINOL was re‐isolable in 98 % yield.

  据报道，前者通过不对称亚砜-镁交换反应使前手性二芳基亚砜1脱对称。相应的底物（1），i Pr 2 Mg和（S）-BINOL的二锂盐（原位制备）提供了（S）-配置的芳基异丙基亚砜2，产率高达91％，产率高达91 ％ee。（S）‐BINOL可重新分离，收率为98％。
• 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.
• Mechanism of the oxidation of aromatic sulfides catalysed by a water soluble iron porphyrin
  作者：Enrico Baciocchi、Maria Francesca Gerini、Osvaldo Lanzalunga、Andrea Lapi、Maria Grazia Lo Piparo

  DOI：10.1039/b209004j

  日期：2003.1.13

  the oxidant. Moreover, no fragmentation products were observed in the oxidation of a benzyl phenyl sulfide whose radical cation is expected to undergo cleavage of the beta C-H and C-S bonds. These results would seem to suggest a direct oxygen atom transfer from the iron-oxo complex to the sulfide. However, competitive experiments between thioanisole (E degree = 1.49 V vs. NHE in H2O) and N,N-dimethylaniline

  在水溶性铁卟啉5,10,15催化的酸性（pH 3）水性介质中，H2O2氧化H2O2氧化了许多芳基硫化物，研究了氧原子转移-电子转移（ET）机理的二分法， 20-四苯基-21H，23H-卟啉-p，p′，p″，p″′-四磺酸氯化三铁（FeTPPSCl）。在这些反应条件下，铁-氧配合物卟啉自由基阳离子P +。Fe（IV）= O应该是活性氧化剂。当研究一系列对位X取代的苯基烷基硫化物（X = OCH3，CH3，H，Br，CN）的氧化时，相应的亚砜是唯一观察到的产物，反应收率和反应性几乎不受X的性质以及烷基的体积。使用H（2）18O或H（2）18O2进行的标记实验清楚地表明，亚砜中的氧原子仅来自氧化剂。此外，在苄基苯基硫醚的氧化中未观察到任何断裂产物，该自由基的阳离子预期会发生βCH和CS键的断裂。这些结果似乎表明氧原子直接从铁-氧配合物转移至硫化物。但是，硫代苯甲醚（H2O中的E度= 1.49 V
• Synthesis of 1-(1-Arylsulfanylalkyl)indoles and 2,2-Bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes by Acid-Catalyzed Reactions of Indoles with Aryl Vinyl Sulfides
  作者：Kazuhiro Kobayashi、Yuu Shirai、Shuhei Fukamachi、Hisatoshi Konishi

  DOI：10.3987/com-09-11867

  日期：——

  We report a facile synthesis of 1-(1-arylsulfanylalkyl)indoles and 2,2-bis[1-(1-arylsulfanylalkyl)indol-3-yl]propanes under mild conditions. Thus, treatment of 3-substituted indoles with aryl vinyl sulfides in dichloromethane at room temperature in the presence of a catalytic amount of (+/-)-camphor-10-sulfonic acid yields the former indole derivatives in moderate to fair yields. 3-Nonsubstituted indoles can be transformed into the latter indole derivatives in satisfactory yields on treatment with excess aryl vinyl sulfides in the presence of a catalytic amount of the acid under similar conditions.