4,4'-sulfinylbis(1,2-dimethylbenzene) | 29146-86-9

• 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: 4,4'-sulfinylbis(1,2-dimethylbenzene)
• 英文别名: di-(3,4-dimethylphenyl) sulfoxide；bis(3,4-dimethylphenyl) sulfoxide,；4-(3,4-Dimethylphenyl)sulfinyl-1,2-dimethylbenzene
• CAS: 29146-86-9
• 化学式: C₁₆H₁₈OS
• 分子量: 258.384
• InChiKey: XOXIKTPTJGGZHG-UHFFFAOYSA-N

物化性质

• 熔点：
  99 °C
• 沸点：
  427.1±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  4,4'-sulfinylbis(1,2-dimethylbenzene) 在 碘苯二乙酸 、 ammonium acetate 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以49%的产率得到4,4′-sulfonimidoylbis(1,2-dimethylbenzene)
  参考文献：
  名称：

  Rh(III)-Catalyzed Oxidative Annulation of Sulfoximines with Arylalkynyl Silanes via Desilylation

  摘要：

  Rh(III) catalyzed oxidative synthesis of 1,2-benzothiazine derivatives using sulfoximine as a directing group under C-H activation strategy is reported. In this study, we utilized arylalkynyl silanes as an alternate for terminal alkynes to obtain the 1,2-benzothiazine derivatives via desilylation pathway. The developed methodology shows a good range of functional group tolerance and furnished the products in moderate yields.

  DOI：

  10.1021/acs.joc.9b00743
• 作为产物：
  描述：

  邻二甲苯 在 氯化亚砜 、 水 作用下， 反应 0.08h， 以92%的产率得到4,4'-sulfinylbis(1,2-dimethylbenzene)
  参考文献：
  名称：

  Highly Rapid and Direct Synthesis of Diaryl Sulfoxides

  摘要：

  芳香化合物在常温下与10 mol%的水共同存在时，能与亚硫酰氯顺利反应，得到相应的对称二芳基亚砜，产率良好至优异，并且具有高的区域选择性。

  DOI：

  10.1055/s-2003-41461

文献信息

• Synthesis of <i>o</i>-Aryloxy Triarylsulfonium Salts via Aryne Insertion into Diaryl Sulfoxides
  作者：Xiaojin Li、Yan Sun、Xin Huang、Lei Zhang、Lichun Kong、Bo Peng

  DOI：10.1021/acs.orglett.6b03840

  日期：2017.2.17

  The aryne insertion into “S═O” bond has been validated recently. This technology is elusively applied to the synthesis of thioethers. In contrast to the reported cases, the reaction described furnished o-aryloxy triarylsulfonium salts, in lieu of thioethers, in good to excellent yields. The reaction is also featured by its exquisite regioselectivity, broad substrate scope, and mild conditions (25 °C)

  芳烃插入“S═O”键的过程最近得到验证。该技术难以用于合成硫醚。与报道的情况相反，所描述的反应提供了以邻苯二甲氧基三芳基ulf盐代替硫醚，具有良好至优异的收率。该反应还具有出色的区域选择性，广泛的底物范围和温和的条件（25°C）。初步的机理研究表明，该反应可能以连续的[2 + 2]环加成/ O-芳基化/质子化途径进行。
• Nickel(II)/ <i>N</i> ‐Heterocyclic Carbene Catalyzed Desulfinylative Arylation by C−S Cleavage of Aryl Sulfoxides with Phenylboronic Acids
  作者：Xiaowen Yi、Kai Chen、Junjun Guo、Wei Chen、Wanzhi Chen

  DOI：10.1002/adsc.202000531

  日期：2020.10.21

  Suzuki‐Miyaura coupling of haloarenes is the most widely used protocol for the synthesis of biphenyls. Organosulfur compounds are promising electrophiles since they are abundant in nature and versatile in organic synthesis. We report here the desulfinylative Suzuki‐Miyaura coupling of aryl sulfoxides with phenylboronic acids using bench‐stable nickel/5‐(2,4,6‐triisopropylphenyl)imidazolylidene[1,5‐a]pyridines

  卤代芳烃的Suzuki-Miyaura偶联是联苯合成中使用最广泛的方案。有机硫化合物是有前途的亲电子试剂，因为它们性质丰富且有机合成用途广泛。我们在此报告使用稳定的镍/ 5-（2,4,6-三异丙基苯基）咪唑基亚甲基[1,5- a ]吡啶作为催化剂将芳基亚砜与苯基硼酸的脱亚磺酰基铃木-宫浦偶合。配体易于从常见的商业化学品制备。该方法适用于对称和不对称的芳基亚砜，并且以高达94％的收率获得了一系列带有各种官能团的联苯。
• BISMALEIMIDE COMPOUND AND PRODUCTION METHOD THEREOF
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：US20210246142A1

  公开（公告）日：2021-08-12

  Provided is a bismaleimide compound having a favorable compatibility with other resins and contributing to a higher Tg. The compound is represented by the following formula (1): wherein A independently represents a tetravalent organic group having a cyclic structure, B independently represents a divalent hydrocarbon group having 6 to 200 carbon atoms, Q independently represents a cyclohexane backbone-containing divalent alicyclic hydrocarbon group having 6 to 60 carbon atoms, W represents B or Q, n represents 1 to 100, m represents 0 to 100, repeating units identified by n and m whose bonding pattern may be alternate, block or random are present in any order, and wherein Q is independently represented by the following formula (2): wherein each of R 1 , R 2 , R 3 and R 4 independently represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, each of x1 and x2 represents a number of 0 to 4.

  提供一种与其他树脂具有良好兼容性并有助于提高Tg的双马来酰亚胺化合物。 该化合物由以下公式（1）表示：其中A独立表示具有环状结构的四价有机基团，B独立表示具有6至200个碳原子的二价碳氢基团，Q独立表示具有6至60个碳原子的环己烷骨架含有的二价脂环碳氢基团，W表示B或Q，n表示1至100，m表示0至100，由n和m标识的重复单元的结合方式可以是交替、块状或随机的任意顺序存在，其中Q由以下公式（2）独立表示：其中R1、R2、R3和R4中的每一个独立表示氢原子或具有1至5个碳原子的烷基基团，x1和x2中的每一个表示0至4的数。
• Scandium Triflate Catalyzed One-Pot Synthesis of Diaryl Sulfoxides
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、R. Srinivasa Rao、S. Praveen Kumar、K. Nagaiah

  DOI：10.1055/s-2002-25330

  日期：——

  Arenes react smoothly with thionyl chloride in the presence of a catalytic amount of scandium triflate at ambient temperature to afford the corresponding symmetrical diaryl sulfoxides in excellent yields with high regioselectivity.

  芳烃在室温下与氯磺酰反应，且在催化量的三氟化钪存在下，顺利生成相应的对称二芳基亚砜，产率极高，区域选择性良好。
• Palladium-Catalyzed Enantioselective C−H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
  作者：Yu-Chao Zhu、Yan Li、Bo-Chao Zhang、Feng-Xu Zhang、Yi-Nuo Yang、Xi-Sheng Wang

  DOI：10.1002/anie.201801146

  日期：2018.4.23

  example of PdII‐catalyzed enantioselective C−H olefination with non‐chiral or racemic sulfoxides as directing groups was developed. A variety of chiral diaryl sulfoxides were synthesized with high enantioselectivity (up to 99 %) through both desymmetrization and parallel kinetic resolution (PKR). This is the first report of PdII‐catalyzed enantioselective C(sp2)−H functionalization through PKR, and

  开发了第一个用非手性或外消旋亚砜作为导向基团的Pd II催化对映选择性CH烯化反应的例子。通过不对称化和平行动力学拆分（PKR）合成了具有高对映选择性（高达99％）的多种手性二芳基亚砜。这是Pd II催化通过PKR进行对映选择性C（sp 2）-H功能化的首次报道，它代表了构建硫手性中心的新策略。