β-phenyl-β-hydroxyethyl phenyl sulfone | 51755-92-1

• 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: β-phenyl-β-hydroxyethyl phenyl sulfone
• 英文别名: 1-phenyl-2-(phenylsulfonyl)ethan-1-ol；2-phenyl-1-phenylsulfonylethan-2-ol；1-phenyl-2-(phenylsulfonyl)ethanol；2-phenylsulfonyl-1-phenylethanol；2-benzenesulfonyl-1-phenyl-ethanol；2-Benzolsulfonyl-1-phenyl-aethanol；2-(benzenesulfonyl)-1-phenylethanol
• CAS: 51755-92-1
• 化学式: C₁₄H₁₄O₃S
• mdl: MFCD18033187
• 分子量: 262.329
• InChiKey: PNFHXJXYVJWVKL-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C
• 沸点：
  487.4±45.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  62.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  β-phenyl-β-hydroxyethyl phenyl sulfone 在 磷酸 作用下， 生成 反式苯基肉桂砜
  参考文献：
  名称：

  Grignard Reagents of Sulfones. I. Preparation and Reactions of β-Phenyl-β-hydroxyethyl Phenyl Sulfone¹

  摘要：

  DOI：

  10.1021/ja01135a062
• 作为产物：
  描述：

  2-(N-methyl-S-phenylsulfonimidoyl)-1-phenylethanol 在 盐酸 、 m-C₆H₄CO₃H 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 以90%的产率得到β-phenyl-β-hydroxyethyl phenyl sulfone
  参考文献：
  名称：

  A Method for the Conversion of Sulfoximines to Sulfones: Application to Polymer-Bound Sulfoximines and to the Synthesis of Chiral Sulfones

  摘要：

  Reaction of N-alkyl, N-aryl, and N-H sulfoximines with m-chloroperbenzoic acid cleanly gives the corresponding sulfones in high yield. In the case of the cleavage of N-alkyl and N-arylsulfoximines, formation of the corresponding nitroso compounds as the other reaction product was proven. Starting from enantio- and diastereopure sulfoximines, a number of chiral sulfones, including the axially chiral sulfone 6 and the sulfonyl-functionalized homoallylic alcohol 8, have been prepared. Reaction of the enantiopure sulfoximine 30 with Merrifield resin gave the polymer-bound sulfoximine 32. Oxidative cleavage of 32 afforded the sulfone 16 in high yield. Deprotonation of the sulfoximine resin 32 and reaction of Li-32 with benzaldehyde and propanal furnished the beta-hydroxysulfoximine resins 33a and 33b, respectively. Oxidative cleavage of 33a and 33b readily afforded the beta-hydroxy sulfones 14a and 14b, respectively.

  DOI：

  10.1002/(sici)1099-0690(200004)2000:8<1457::aid-ejoc1457>3.0.co;2-g

文献信息

• Enantioselective reduction of α-substituted ketones mediated by the boronate ester TarB-NO2
  作者：Scott Eagon、Nicholas Ball-Jones、Dustin Haddenham、Jaime Saavedra、Cassandra DeLieto、Matthew Buckman、Bakthan Singaram

  DOI：10.1016/j.tetlet.2010.09.146

  日期：2010.12

  A facile and mild reduction procedure is reported for the preparation of chiral secondary alcohols prepared from α-substituted ketones using sodium borohydride and the chiral boronate ester (l)-TarB-NO2. Direct reduction of substituted ketones bearing Lewis basic heteroatoms generally provided secondary alcohols of only modest enantiomeric excess likely due to either competition between the target

  据报道，使用硼氢化钠和手性硼酸酯（1）-TarB-NO 2由α-取代的酮制备手性仲醇的方法简便而温和。直接还原带有Lewis碱性杂原子的取代酮通常可提供仅适度对映体过量的仲醇，这可能是由于目标羰基与TarB-NO 2中Lewis酸性硼原子处的官能化侧链之间的竞争或α的增加的空间体积造成的-侧链。作为替代方法，使用TarB-NO 2合成这些底物通过两步程序，包括将α-卤代酮还原为手性末端环氧化物，然后通过各种亲核试剂打开区域选择性/区域特异性环氧化物。该方法提供了各种功能化的仲醇，包括β-羟基醚，硫醚，腈和胺，对映体过量为94％，收率最高为98％。
• Catalytic asymmetric conjugate boration of α,β-unsaturated sulfones
  作者：Abraham L. Moure、Ramón Gómez Arrayás、Juan C. Carretero

  DOI：10.1039/c1cc11949d

  日期：——

  The alpha,beta-unsaturated sulfones are suitable activated olefins in catalytic asymmetric conjugate beta-boration. These substrates undergo smooth conjugate addition of bis(pinacolato)diboron [B(2)(pin)(2)] catalyzed by nonracemic Cu(I)-diphosphine complexes to provide, upon subsequent oxidation, beta-hydroxy sulfones in good yields and high enantiocontrol.

  α，β-不饱和砜是催化不对称共轭β-硼酸酯化反应中合适的活化烯烃。这些底物通过非外消旋的Cu（I）-二膦配合物催化双（pinacolato）diboron [B（2）（pin）（2）]的平滑共轭加成，从而在随后的氧化反应中，以高收率和高收率提供β-羟基砜对映体控制。
• One-Pot Synthesis of β-Hydroxysulfones and Its Application in the Preparation of Anticancer Drug Bicalutamide
  作者：Yajun Wang、Wei Jiang、Congde Huo

  DOI：10.1021/acs.joc.7b01371

  日期：2017.10.6

  reduction of peroxides for the synthesis of complex β-hydroxysulfone derivatives from phenthiols and alkenes. This method has several advantageous characteristics, including readily available substrates, low-cost and environmental benign reagents, nontoxic and renewable solvents, and mild reaction conditions. The application of this transformation to the multigram-scale preparation of the anticancer drug bicalutamide

  已经开发了一种有效的一锅多步策略，包括烯烃的自氧化双官能化，硫化物的氧化以及过氧化物的进一步还原，用于由苯硫酚和烯烃合成复杂的β-羟基砜衍生物。该方法具有几个有利的特征，包括容易获得的底物，低成本和环境友好的试剂，无毒和可再生的溶剂以及温和的反应条件。完成了该转化在抗癌药物比卡鲁胺的克级制备中的应用。
• Iodine-Triggered Aerobic Oxysulfonylation of Styrenes
  作者：Khokan Choudhuri、Tapas Kumar Achar、Prasenjit Mal

  DOI：10.1002/adsc.201700772

  日期：2017.10.25

  iodine-triggered dioxygen activation in oxysulfonylation reactions of unactivated olefins using sulfonyl hydrazides and iodine as catalyst is reported here. In one pot, near quantitative syntheses of β-hydroxysulfones were achieved at 70 °C, within 7 h, in acetonitrile and under aerobic conditions. A plausible mechanism is established by radical trapping and 18O labelling experiments for the operationally simple

  在此报道了使用磺酰肼和碘作为催化剂的未活化烯烃的氧磺酰化反应中的碘触发的双氧活化。在一个锅中，在乙腈中和有氧条件下，在70°C，7 h之内，即可完成近乎定量的β-羟基砜合成。通过自由基捕获和18 O标记实验建立了可行的机制，以实现操作简单，有效且经济上可行的转化。建议在无金属和温和条件下直接活化空气中的氧，以进行烯烃的氧磺酰化。
• Catalyst-free oxidation of sulfides to sulfoxides and diethylamine catalyzed oxidation of sulfides to sulfones using Oxone as an oxidant
  作者：R. V. Kupwade、S. S. Khot、U. P. Lad、U. V. Desai、P. P. Wadgaonkar

  DOI：10.1007/s11164-017-3026-0

  日期：2017.12

  journey from the failure of our attempts in controlled oxidation of sulfides to sulfoxides using an Oxone®–KBr combination to our success in the development of a catalyst-free protocol for the oxidation of sulfides to sulfoxides using Oxone as an oxidant. We also describe the failure of our attempts at the oxidation of sulfides to sulfones using an excess of Oxone–KBr as well as Oxone, and our success

  摘要 我们在这里描述从我们的尝试中硫化物的控制氧化为亚砜使用过硫酸氢钾失败我们的旅程® -KBr结合我们在无催化剂协议的发展，为硫化物氧化为使用臭氧作为氧化剂亚砜成功。我们还描述了使用过量的Oxone-KBr和Oxone尝试将硫化物氧化为砜的尝试的失败，以及我们成功开发了快速，可扩展且无色谱的硫化物氧化为砜的方案的成功案例。使用二乙胺-丙酮作为前所未有的催化剂-氧化剂组合。 图形概要