1-chloro-3-((p-tolylsulfinyl)methyl)benzene | 344302-83-6

• 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: 1-chloro-3-((p-tolylsulfinyl)methyl)benzene
• 英文别名: 1-chloro-3-(p-tolylsulfinylmethyl)benzene；m-chlorobenzyl p-tolyl sulfoxide；1-chloro-3-[(4-methylphenyl)sulfinylmethyl]benzene
• CAS: 344302-83-6
• 化学式: C₁₄H₁₃ClOS
• 分子量: 264.776
• InChiKey: UANJEYRUDIIDOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.96
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-chloro-3-((p-tolylsulfinyl)methyl)benzene 以9%的产率得到
  参考文献：
  名称：

  ITOH, OSAMU;NUMATA, TATSUO;YOSHIMURA, TOSHIAKI;OAE, SHIGERU, BULL. CHEM. SOC. JAP., 1983, 56, N 1, 266-269

  摘要：

  DOI：
• 作为产物：
  描述：

  3-chlorobenzyl 4-methylphenyl sulfide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 1-chloro-3-((p-tolylsulfinyl)methyl)benzene
  参考文献：
  名称：

  Synthesis of Sulfur-Bridged Polycycles via Pd-Catalyzed Dehydrogenative Cyclization

  摘要：

  A general approach to sulfur-bridged polycycles by palladium-catalyzed double C(sp(2))-H bond oxidative cyclization is presented. This protocol afforded diverse sulfur-bridged five-, six-, and seven-membered polycycles in moderate to good yields with a tolerance for a wide variety of functional groups. A sulfide-bridged six-membered pyrene-thienoacene compound was synthesized readily using this method, and excellent performance for photoluminescence quantum yield was observed.

  DOI：

  10.1021/ol502127j

文献信息

• Metal-free oxidative coupling of alkyl chlorides with thiols: An efficient access to sulfoxides
  作者：Qian Liu、Xiaoqian Zhao、Feng Xu、Gaoqiang Li

  DOI：10.1016/j.tetlet.2019.151492

  日期：2020.2

  An efficient and step-economical access to sulfoxides from thiols and alkyl halides in the presence of I2O5 and DBU via direct oxidative couplings is described here. It is the first case that combined Williamson sulfide synthesis and subsequent sulfide oxidation into one step manipulation for sulfoxides preparation. This protocol features wide substrate scope, mild and metal-free conditons, the use

  本文描述了在I 2 O 5和DBU存在下，通过直接氧化偶合从硫醇和烷基卤化物高效，经济地获取亚砜的方法。这是第一种将威廉姆森硫化物合成和随后的硫化物氧化结合起来一步一步进行亚砜制备的情况。该协议具有广泛的底物范围，温和无金属的条件，使用天然丰富的起始原料以及避免过度氧化的特点。
• The Epoxidation of Carbonyl Compounds with a Benzyne-Triggered Sulfur Ylide
  作者：Mei-Mei Lou、Han Wang、Li Song、Hong-Yi Liu、Zhong-Qiu Li、Xiao-Shuang Guo、Fu-Geng Zhang、Bin Wang

  DOI：10.1021/acs.joc.6b00760

  日期：2016.7.15

  An efficient method for the synthesis of epoxides from carbonyl compounds, sulfoxides, and benzyne is presented. The strategy involved an epoxidation by a sulfur ylide which is formed in situ from sulfoxide and benzyne through the S–O bond insertion and deprotonation. This one-pot reaction proceeds under mild and base-free conditions, providing a convenient way to introduce the substituted methylene

  提出了一种由羰基化合物，亚砜和苯炔合成环氧化物的有效方法。该策略涉及由亚砜和亚砜通过S-O键插入和去质子化在原位形成的叶立德进行环氧化。该一锅法反应在温和且无碱的条件下进行，提供了将取代的亚甲基引入羰基碳的简便方法。
• Palladium(II)-Catalyzed <i>ortho</i>-Olefination of Arenes Applying Sulfoxides as Remote Directing Groups
  作者：Binjie Wang、Chuang Shen、Jinzhong Yao、Hong Yin、Yuhong Zhang

  DOI：10.1021/ol402921w

  日期：2014.1.3

  A novel palladium-catalyzed ortho-C(sp(2))-H olefination protocol has been developed by the use of sulfoxide as the directing group. Importantly, relatively remote coordination can be accessed to achieve the ortho olefination of benzyl, 2-arylethyl, and 3-arylpropenyl sulfoxide substrates, and the olefinated sulfoxide can be easily transformed to other functionalities.