bis{2-hydroxy-2-phenylethyl} disulfide | 35034-34-5

• 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: bis{2-hydroxy-2-phenylethyl} disulfide
• 英文别名: bis-(2-hydroxyethylphenyl)disulfide；Bis-(2-hydroxy-2-phenyl-ethyl)-disulfid；2-[(2-Hydroxy-2-phenylethyl)disulfanyl]-1-phenylethanol
• CAS: 35034-34-5
• 化学式: C₁₆H₁₈O₂S₂
• 分子量: 306.45
• InChiKey: VUYDNDKAMALDBG-UHFFFAOYSA-N

物化性质

• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  91.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  bis{2-hydroxy-2-phenylethyl} disulfide 在 hydridotetakis(triphenylphosphine)rhodium(I) 、 三氟甲磺酸 、 三对苯甲基膦 、 三氟乙酸 作用下， 以 氯苯 、 丙酮 为溶剂， 反应 49.0h， 生成 (R)-2-hydroxy-2-phenylethyl octyl disulfide
  参考文献：
  名称：

  Equilibrium shift induced by chiral nanoparticle precipitation in rhodium-catalyzed disulfide exchange reaction

  摘要：

  Chiral silica (P)-nanoparticles grafted with (P)-helicene recognize the molecular structure of a chiral diol disulfide in the presence of monool disulfide and dibutyl disulfide. The (P)-nanoparticles selectively adsorb the diol disulfide, aggregate, and precipitate from solution. Under rhodium-catalyzed equilibrium among three disulfides, the diol disulfide is removed from solution by precipitation, which induces an equilibrium shift in the solution. By conducting the precipitation experiment twice, we obtained the dial disulfide in 37% yield from a statistical 1:2:1 equilibrium mixture of three disulfides. The method is applied to a racemic monool disulfide, and an optically active dial disulfide is obtained via kinetic resolution and equilibrium shift. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.05.106
• 作为产物：
  描述：

  氧化苯乙烯 在 Ca(BH₂S₃)2 作用下， 以 四氢呋喃 为溶剂， 反应 1.2h， 以84%的产率得到bis{2-hydroxy-2-phenylethyl} disulfide
  参考文献：
  名称：

  使用硫化硼氢化钙 [Ca(S3BH2)2] 有效还原有机化合物，这是一种新型稳定的改性硼氢化物试剂

  摘要：

  摘要 通过NaBH2S3 与Ca、Mg 和Be 氯化物在干燥THF 中的复分解反应制备了硫化钙、镁和硼氢化铍，并介绍了金属阳离子交换对其稳定性和反应性的影响。在这项研究中，我们已经表明 Ca(BH2S3)2 比其 Mg、Be 和 Na 类似物更稳定且更具反应性。Ca(BH2S3)2 可以很容易地将羰基化合物，如醛、酮、丙烯、α-二酮、α-β-不饱和羰基化合物、芳酰基叠氮化物和羧酸氯化物还原成相应的醇，产率很高。环氧化物也受该试剂影响并以良好的产率产生它们的对称二羟基二硫化物。

  DOI：

  10.1080/10426500008043654

文献信息

• Highly Efficient, Regio- and Stereoselective Ring Opening of Epoxides and Thiiranes with Ce(OTf)₄
  作者：N. Iranpoor、M. Shekarriz、F. Shiriny

  DOI：10.1080/00397919808005728

  日期：1998.1

  Abstract Ceric triflate, Ce(OTf)4 is used as an efficient catalyst for ring opening of epoxides in the presence of alcohols, water, and acetic acid. The reactions proceed with high regio and stereoselectivity and in excellent yields. The reaction of R(+) styrene oxide with methanol occurs with excellent optical purity. Ring opening of thiiranes in alcohols, water and acetic acid followed by dimerisation

  摘要 三氟甲磺酸铈，Ce(OTf)4 被用作在醇、水和乙酸存在下环氧化物开环的有效催化剂。该反应以高区域选择性和立体选择性以及优异的产率进行。R(+) 氧化苯乙烯与甲醇的反应具有极好的光学纯度。在这种试剂的存在下，硫杂丙环在醇、水和乙酸中开环，然后二聚成相应的二硫化物。还描述了一种从硫杂丙烷和 Ce(OTf)4 制备二噻烷的温和方法。
• Iodine and iodine supported on polyvinylpyrrolidone as catalysts and reagents for alcoholysis, hydrolysis, and acetolysis of epoxides and thiiranes
  作者：Nasser Iranpoor、Bahman Tamami、Khodabakhsh Niknam

  DOI：10.1139/v97-626

  日期：1997.12.1

  Iodine and iodine supported on polyvinylpyrrolidone (betadine) have been used as catalysts for ring opening of epoxides and as reagent for ring-opening dimerization of thiiranes in alcohols, water, and acetic acid. The reactions occur with high regio-, chemo-, and stereoselectivity. The reaction of R-(+)-styrene oxide with I₂ supported on PVP in methanol was found to be very stereospecific and the product was isolated in 93% ee. Keywords: iodine, support, polyvinylpyrrolidone, ring opening, epoxides, thiiranes.

  聚乙烯吡咯烷酮支持的碘和碘（贝他碘）已被用作环氧化物开环的催化剂，以及硫环烷在醇类、水和乙酸中开环二聚的试剂。这些反应具有高的位置选择性、化学选择性和立体选择性。在甲醇中，R-(+)-苯乙烯环氧化物与聚乙烯吡咯烷酮支持的I₂反应具有非常具有立体特异性，产物以93%的ee分离。关键词：碘、支持、聚乙烯吡咯烷酮、环氧化物、硫环烷。
• Reactions of epoxides and episulfides with electrophilic halogens
  作者：Nasser Iranpoor、Habib Firouzabadi、Maryam Chitsazi、Abbas Ali Jafari

  DOI：10.1016/s0040-4020(02)00699-3

  日期：2002.8

  conversion of epoxides into β-bromoformates using Ph3PBr2, Ph3P/N-bromosuccinimdes (NBS) and or Ph3P/2,4,4,6-tetrabromo-2,5-cyclohexadiene-1-one (TABCO) in DMF. Epoxides in the presence of Ph3P/I2 were converted into olefins immediately in excellent yields. The application of NBS, NCS, and TABCO as compounds carrying electrophilic halogens for the highly selective alcoholysis of epoxides and dimerization

  描述了一种使用Ph 3 PBr 2，Ph 3 P / N-溴代琥珀酰亚胺（NBS）和Ph 3 P / 2,4,4,4,6-四溴-2,5-将环氧化物转化为β-溴甲酸酯的新方法。 DMF中的环己二烯-1-酮（TABCO）。在存在Ph 3 P / I 2的情况下，环氧化物立即以优异的收率转化为烯烃。还描述了NBS，NCS和TABCO作为携带亲电卤素的化合物在环氧化物的高选择性醇解和环硫化物的二聚化或醇解二聚化中的应用。
• AMINOPROPYL SILICA GEL SUPPORTED IODINE AS CATALYST IN NUCLEOPHILIC RING OPENING OF EPOXIDES AND EPISULFIDES
  作者：B. Tamami、N. Iranpoor、H. Mahdavi

  DOI：10.1081/scc-120003617

  日期：2002.1

  ABSTRACT Silica gel functionalized by aminopropyl group was prepared. Iodine was then supported on this inorganic polymer and used as a stable and efficient heterogeneous catalyst for nucleophilic ring opening reactions of epoxides and episulfides in different nucleophilic solvents such as alcohols, water and acetic acid.

  摘要制备了氨基丙基官能化硅胶。然后将碘负载在这种无机聚合物上，并用作稳定有效的多相催化剂，用于环氧化物和环硫化物在不同亲核溶剂（如醇、水和乙酸）中的亲核开环反应。
• A NEW STABLE MODIFIED BOROHYDRIDE REAGENT, EFFICIENT REDUCTION OF DIFFERENT FUNCTIONAL GROUPS WITH SULFURATED BARIUM BOROHYDRIDE [BA(BH₂S₃)₂] IN DRY THF
  作者：Habib Firouzabadi、Mahboobeh Ghadami

  DOI：10.1080/10426500008076533

  日期：2000.1.1

  Barium and strontium sulfurated borohydrides, Ba(BH2S3)(2),Sr(BH2S3)(2) the two newly introduced modified borohydride agents, are prepared from NaBH2S3 by metathesis reaction with BaCl2 and SrCl2 in good yields. Ba(BH2S3)(2) is more stable and more reactive than Sr(BW2S3)(2) The reducing ability of Ba(BH2S3)(2) for the reduction of aldehydes, ketones, alpha,beta -unsaturared carbonyl compounds, azides, nitro compounds, and cleavage of epoxides in dry THF is described.