2-(苯亚磺酰)-1-苯基乙醇 | 49639-26-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(苯亚磺酰)-1-苯基乙醇
• 英文名称: 1-phenyl-2-(phenylsulfinyl)ethanol
• 英文别名: 1-phenyl-2-(phenylsulfinyl)ethan-1-ol；2-(benzenesulfinyl)-1-phenylethanol
• CAS: 49639-26-1
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: HDGGJVKMRKWGGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(苯亚磺酰)-1-苯基乙醇 在 磺酰氯 作用下， 生成 (1-chloro-2-(phenylsulfonyl)ethyl)benzene
  参考文献：
  名称：

  Neighboring Group Participation in the Halogenation of Sulfoxides

  摘要：

  PhS(O)(CH₂)ₙCH₂OH(n = 1–3) 在氯化亚砜氯在−78°或0°的氯化亚砜中反应，得到相应的PhSO₂(CH₂)ₙCH₂Cl。有证据表明，环状烷氧氧代磺鎓盐是这些转化中间体。当n = 4时，只观察到对亚砜功能的α氯化。烷磺酰基羧酸PhS(O)(CH₂)ₙCO₂H (n = 1–3) 和酰胺PhS(O)(CH₂)ₙCONH₂ (n = 1–3) 也与SO₂Cl₂反应。当n = 1或3时，两种化合物均观察到α氯化。当n = 2时，产物分别为3-苯基磺酰基丙酰氯和3-苯基磺酰基丙腈。

  DOI：

  10.1139/v73-256
• 作为产物：
  描述：

  2-(苯亚磺酰)-1-苯基乙酮 在 二异丁基氢化铝 、 zinc(II) chloride 作用下， 生成 2-(苯亚磺酰)-1-苯基乙醇
  参考文献：
  名称：

  Chiral sulfur-reagents for the preparation of optically active epoxides

  摘要：

  Acyclic chiral sulfides which could be easily synthesized in both enantiomeric forms leading to poor yields and/or to racemic epoxides, Eliel's oxathiane reagent was used and proved to provide chiral trans diarylepoxides in high yield (70-80%) and enantiomeric purities up to 70-100%, with no rearrangement problems. It was also found that phase-transfer conditions were the easiest and the most efficient for these reactions.

  DOI：

  10.1016/s0040-4020(01)88764-0

文献信息

• Acid-Catalyzed Oxidative Addition of Thiols to Olefins and Alkynes for a One-Pot Entry to Sulfoxides
  作者：Martin Klussmann、Hui-Lan Yue

  DOI：10.1055/s-0035-1562480

  日期：——

  An oxidative variant of the thiol-ene reaction has been developed, achieving the direct addition of thiols to olefins to form sulfoxides. The reaction uses tert-butyl hydroperoxide as oxidant and methanesulfonic acid as catalyst. The latter is believed to catalyze the oxidation of the intermediate sulfide to the sulfoxide. No special precautions are necessary to exclude oxygen, yet the products are

  已开发出硫醇-烯反应的氧化变体，实现了硫醇与烯烃的直接加成以形成亚砜。该反应以叔丁基过氧化氢为氧化剂，甲磺酸为催化剂。据信后者催化中间体硫化物氧化成亚砜。不需要特殊的预防措施来排除氧气，但产物在 β 位没有氧化的情况下形成。苯乙烯、丙烯酸衍生物、炔烃和苯硫酚的产率最高，而脂肪族烯烃和硫醇的效果较差。
• Synthesis of Sulfoxides by the Hydrogen Peroxide Induced Oxidation of Sulfides Catalyzed by Iron Tetrakis(pentafluorophenyl)porphyrin:  Scope and Chemoselectivity
  作者：Enrico Baciocchi、Maria Francesca Gerini、Andrea Lapi

  DOI：10.1021/jo049879h

  日期：2004.5.1

  The oxidation of sulfides with H2O2 catalyzed by iron tetrakis(pentafluorophenyl)porphyrin in EtOH is an efficient and chemoselective process. With a catalyst concentration 0.03−0.09% of that of the substrate, sulfoxides are obtained with yields generally around 90−95% of isolated product. With vinyl and allyl sulfides, no epoxidation is observed. With a catalyst concentration between 0.09% and 0.25%

  四（五氟苯基）卟啉铁在EtOH中催化的H 2 O 2氧化硫化物是一种有效的化学选择过程。在催化剂浓度为底物浓度的0.03-0.09％的情况下，获得的亚砜的收率通常约为分离产物的90-95％。对于乙烯基和烯丙基硫化物，未观察到环氧化。催化剂浓度为底物浓度的0.09％至0.25％，可以以几乎定量的产率获得砜，并且在亚砜的合成中观察到相同的高化学选择性。
• Synthesis of 1,1-diarylethylenes
  作者：Meng-Yang Chang、Yi-Hsuan Huang、Heui-Sin Wang

  DOI：10.1016/j.tet.2016.04.018

  日期：2016.6

  A facile route toward 1,1-diarylethylenes 6 has been developed in good yields via mCPBA-promoted oxidation of β-hydroxysulfides 2, BF3·OEt2-mediated Friedel–Crafts reaction of the resulting β-hydroxysulfoxides 3 with oxygenated benzenes 4, followed by Pd/C-mediated [2,3]-sigmatropic rearrangement of sulfoxides 5. The protocol provides a short-term, easy-operational, inexpensive reagent, mild condition

  通过m CPBA促进的β-羟基硫化物2，BF 3 ·OEt 2介导的Friedel-Crafts反应生成的β-羟基亚砜3与含氧苯4的反应，已经以高收率开发了一条通往1,1-二芳基乙烯6的简便路线。，然后是Pd / C介导的亚砜5的[2,3]-σ重排。该协议提供了一种短期，易于操作，廉价的试剂，温和的条件以及可快速获得的转化方法。
• Diastereoselective Synthesis of -Hydroxy Sulfoxides: Enzymatic and Biomimetic Approaches
  作者：Stefano Colonna、Vincenza Pironti、Francesca Zambianchi、Gianluca Ottolina、Nicoletta Gaggero、Giuseppe Celentano

  DOI：10.1002/ejoc.200600624

  日期：2007.1

  Stereoselectivities of up to 98 % have been found in the enzymatic synthesis of β-hydroxy sulfoxides catalyzed by cyclohexanone monooxygenase (CHMO). The diastereoselectivity of the “one-pot” preparation of the title compounds in the presence of bovine serum albumin has also been investigated. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

  在由环己酮单加氧酶 (CHMO) 催化的 β-羟基亚砜的酶促合成中，已发现立体选择性高达 98%。还研究了在牛血清白蛋白存在下“一锅”制备标题化合物的非对映选择性。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Air Oxidation of Sulfides to Sulfoxides Using BiBr₃-Bi(NO₃)₃as a Binary Catalyst
  作者：Naoki Komatsu、Masato Uda、Hitomi Suzuki

  DOI：10.1246/cl.1997.1229

  日期：1997.12

  Selective air oxidation of sulfides to sulfoxides was accomplished with a binary catalytic system, BiBr3-Bi(NO3)3, in high yields under aerial ambient conditions. This oxygenation requires neither an aldehyde nor a transition metal complex.

  在空气环境条件下，采用二元催化体系BiBr3-Bi(NO3)3成功选择性地将硫化物氧化为亚砜，并且产率较高。这一氧化反应不需要醛或过渡金属配合物。