2-bromoethyl phenyl sulfoxide | 193097-47-1

• 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: 2-bromoethyl phenyl sulfoxide
• 英文别名: α-Bromethylphenylsulfoxid；2-Bromoethylsulfinylbenzene；2-bromoethylsulfinylbenzene
• CAS: 193097-47-1
• 化学式: C₈H₉BrOS
• 分子量: 233.129
• InChiKey: JFPLMOCDZGOUBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  2-bromoethyl phenyl sulfoxide 在 N-氯代丁二酰亚胺 、 potassium tert-butylate 作用下， 以 四氯化碳 为溶剂， 反应 26.08h， 生成 di-t-butyl 2-(2-propenyl)-2-[2-chloro-2-(phenylsulfinyl)ethyl]propanedioate
  参考文献：
  名称：

  Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals

  摘要：

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00472-9
• 作为产物：
  描述：

  苯基溴代乙基硫醚 在 双氧水 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-bromoethyl phenyl sulfoxide
  参考文献：
  名称：

  α-和β-杂原子取代的乙基苯基亚砜的热解

  摘要：

  用1-氯乙基苯基亚砜(1)对α-和β-杂原子取代乙基苯基亚砜的热分解机理进行了研究；两个非对映异构体 1-乙酰氧基乙基（取代苯基）亚砜 (2a) 和 (2b)；和2-氯乙基苯基、2-溴乙基苯基和2-甲氧基乙基苯基亚砜(3、4、5)。在 160°C 下，1 的热解速率比用作参考的乙基苯基亚砜快 4.8 倍，而 2a 和 2b 的热解速率分别快 107 和 155 倍。结果表明，α-杂原子上的孤对电子比它们的电负性具有更大的速率加速效应。2a 和 2b 的苯基的取代基效应产生了正的哈米特 ρ 值（ρ a = 0.76 和 ρ b = 0.80 vs. σ）。2a 和 2b 的激活参数如下： 2a, ΔH ‡ = 112 kJmol−1，ΔS ‡ = −20 JK−1mol−1；2b，ΔH ‡ = 107 kJmol−1，ΔS ‡ = −29 JK-1mol−1。观察到 1-乙酰氧基乙基-2,2

  DOI：

  10.1080/10426501003773563

文献信息

• A study of the functional group compatibility of sulfoximination methods
  作者：Sylvaine Cren、Taryn C. Kinahan、Catharine L. Skinner、Heather Tye

  DOI：10.1016/s0040-4039(02)00378-7

  日期：2002.4

  range of sulfoxides possessing functionalised side-chains using mesitylene sulfonyl hydroxylamine or iminoiodane reagents is discussed. The use of iminoiodane reagents possessing removable protecting groups (p-nosyl and Ses) is reported along with conditions for the deprotection of the sulfoximine adducts.

  讨论了使用均三甲苯磺酰基羟胺或亚氨基碘烷试剂对一系列具有官能化侧链的亚砜进行亚硫酸盐化反应。据报道，使用具有可去除的保护基（对-壬基和Ses）的亚氨基碘烷试剂以及使亚磺酰亚胺加合物脱保护的条件。
• Reaction of α-Halosulfoxides with Amines
  作者：Tatsuo Numata、Shigeru Oae

  DOI：10.1246/bcsj.45.2794

  日期：1972.9

  initial nucleophilic substitution at α-carbon of the sulfoxide to form aminomethyl p-toly sulfoxide, followed by rearrangement to the corresponding sulfenate, and subsequent attack of the amine at the sulfur atom of the sulfenate to form the final product. Meanwhile, a facile interconversion of alkoxymethyl p-toly sulfoxide and corresponding sulfenate was also observed.

  当用甲基硫醇钠或乙醇钠处理旋光溴甲基对甲苯亚砜时，以良好的收率获得旋光α-取代的甲基对甲苯亚砜。相比之下，与仲胺的反应以几乎定量的产率产生了非手性对甲苯次磺酰胺、亚甲基二胺和胺氢溴酸盐。据推测，与胺的反应通过亚砜的 α-碳上的初始亲核取代进行，形成氨基甲基对甲苯基亚砜，然后重排为相应的次磺酸盐，随后胺攻击次磺酸盐的硫原子以形成最终产品。同时，还观察到烷氧基甲基对甲苯基亚砜和相应的次磺酸盐的容易相互转化。
• A comparison of the oxidative reactivities of mustard (2,2'-dichlorodiethyl sulfide) and bivalent sulfides
  作者：Yu Chu Yang、Linda L. Szafraniec、William T. Beaudry、Franklin A. Davis

  DOI：10.1021/jo00298a055

  日期：1990.5
• Novel positive inotropic agents: synthesis and biological activities of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinone derivatives
  作者：Takafumi Fujioka、Shuji Teramoto、Toyoki Mori、Tetsumi Hosokawa、Takumi Sumida、Michiaki Tominaga、Youichi Yabuuchi

  DOI：10.1021/jm00098a003

  日期：1992.10

  A series of 6-(3-amino-2-hydroxypropoxy)-2(1H)-quinolinones has been synthesized and evaluated for positive inotropic activity on the canine heart. Some of these derivatives have a potent activity with none or negative chronotropic effect in isolated, blood-perfused dog heart preparations. They also display a high selectivity for positive inotropic effect over chronotropic and vasodilatory effects in anesthetized dogs. (+/-)-6-[2-Hydroxy-3-[(3-methoxybenzyl)amino]propoxy]-2(1H)-quinolinone (39) and (+/-)-6-[3-(3,4-dimethoxybenzyl)amino]-2-hydroxypropoxy]-2(1H)-quinolinone (40) were further investigated in conscious dogs. After iv administration, they did not affect heart rate or mean blood pressure at the dose producing a 50% increase in the peak of the first derivative of the left ventricular pressure. The compounds (39,OPC-18750, and 40,OPC-18790) are the most promising agents with desirable biological activities, and now are currently undergoing clinical evaluation.
• Generation and intramolecular cyclization of α-sulfinyl and α-sulfonyl radicals
  作者：Bor-Wen Ke、Chao-Hsiung Lin、Yeun-Min Tsai

  DOI：10.1016/s0040-4020(97)00472-9

  日期：1997.6

  alpha-Phenylsulfinyl and alpha-Phenylsulfonyl radicals are generated by the reactions of alpha-chlorosulfoxides and alpha-chlorosulfones with tributyltin hydride, respectively. High reaction concentration (0.2 M) is required to ensure efficient generations of these radicals. The 5-exo-type intramolecular cyclizations of these radicals are studied. The cyclization is most successful when the olefin is terminally substituted with an ester group. The sulfinyl group only induces mild diastereoselectivity on the cyclization. (C) 1997 Elsevier Science Ltd.