syn-/anti-1,2-Epoxy-3-phenylbutan-3-ol | 101017-92-9

• 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: syn-/anti-1,2-Epoxy-3-phenylbutan-3-ol
• 英文别名: 1-(oxiran-2-yl)-1-phenylethan-1-ol；1-(oxiran-2-yl)-1-phenylethanol
• CAS: 101017-92-9
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: PTECEJYIAHGTJC-UHFFFAOYSA-N

物化性质

• 沸点：
  281.0±13.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  syn-/anti-1,2-Epoxy-3-phenylbutan-3-ol 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以40%的产率得到4-羟基-3-苯基-2-丁酮
  参考文献：
  名称：

  Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms

  摘要：

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.

  DOI：

  10.1021/jo00074a019
• 作为产物：
  描述：

  2-phenylbut-3-en-2-ol 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到syn-/anti-1,2-Epoxy-3-phenylbutan-3-ol
  参考文献：
  名称：

  受基质控制的产品差异：将CO2转化为杂环产品

  摘要：

  取代的环氧醇和胺可通过不同的机械歧管，将底物控制的CO 2转化为多种杂环结构。这种新方法通过胺或醇单元对CO 2的初始活化，导致了源自CO 2衍生产品的异常范围，从而在温和的反应条件下为分子内环氧开环提供了亲核试剂。对照实验通过遵循S N i途径的亲核试剂开环步骤和5-exo-tet环化作用，支持了胺/醇片段在该过程中的关键作用，从而形成了杂环骨架。

  DOI：

  10.1002/anie.201511521

文献信息

• Organocatalyzed Domino [3+2] Cycloaddition/Payne-Type Rearrangement using Carbon Dioxide and Epoxy Alcohols
  作者：Sergio Sopeña、Mariachiara Cozzolino、Cristina Maquilón、Eduardo C. Escudero-Adán、Marta Martínez Belmonte、Arjan W. Kleij

  DOI：10.1002/anie.201803967

  日期：2018.8.27

  cyclic carbonate under thermodynamic control. The latter are conveniently trapped in situ, providing overall a new domino process for synthetically elusive heterocyclic scaffolds. Control experiments provide a rationale for the observed cascade reactions, which demonstrate similarity to the well‐known Payne rearrangement of epoxy alcohols.

  已经开发了一种空前的有机催化方法，用于从三或四取代的肟酮和二氧化碳制得高度取代的环状碳酸酯。该协议涉及在温和，无添加剂和无金属的条件下使用简单廉价的超碱，以初步形成较少取代的碳酸酯产物，该产物在热力学控制下平衡为三或什至四取代的环状碳酸酯。后者被方便地原位捕获，为合成难以捉摸的杂环支架提供了总体上新的多米诺骨牌工艺。对照实验为观察到的级联反应提供了理论依据，该级联反应证明与众所周知的环氧醇的佩恩重排相似。
• Catalytic Enantioselective Epoxidation of Tertiary Allylic and Homoallylic Alcohols
  作者：José Luis Olivares-Romero、Zhi Li、Hisashi Yamamoto

  DOI：10.1021/ja401182a

  日期：2013.3.6

  for the enantioselective epoxidation of both tertiary allylic and homoallylic alcohols catalyzed by Hf(IV)-bishydroxamic acid (BHA) complexes is described. Asymmetric epoxidation, kinetic resolution, and desymmetrization have been developed, demonstrating the flexible nature of the Hf(IV)-BHA system. This is the first report in which these substrates were obtained with enantioselectivities of up to

  描述了一种由 Hf (IV)-双异羟肟酸 (BHA) 配合物催化的叔烯丙醇和高烯丙醇的对映选择性环氧化的有效且通用的方法。不对称环氧化、动力学拆分和去对称化已经得到发展，证明了 Hf(IV)-BHA 系统的灵活性。这是获得这些底物的对映选择性高达 99% 的第一份报告。
• Muscarinic Receptor Antagonists
  申请人：Salman Mohammad

  公开号：US20080280883A1

  公开（公告）日：2008-11-13

  This present invention generally relates to muscarinic receptor antagonists which are useful, among other uses, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to the process for the preparation of disclosed compounds, pharmaceutical compositions containing the disclosed compounds, and the methods for treating diseases mediated through muscarinic receptors.

  本发明通常涉及可用于治疗通过毒蕈碱受体介导的呼吸系统、泌尿系统和胃肠系统的各种疾病的毒蕈碱受体拮抗剂。该发明还涉及揭示化合物的制备过程、含有揭示化合物的制药组合物以及治疗通过毒蕈碱受体介导的疾病的方法。
• Stereoselective construction of quaternary centers at ambient temperature by the highly stereocontrolled migration of groups containing sp-, sp2-, and sp3-hybridized carbon atoms
  作者：Charles M. Marson、Andrew J. Walker、Jane Pickering、Adrian D. Hobson、Roger Wrigglesworth、Simon J. Edge

  DOI：10.1021/jo00074a019

  日期：1993.10

  A very highly diastereoselective semipinacol rearrangement of 2,3-epoxy alcohols mediated by tin(IV) chloride at ambient temperatures is shown to be applicable to a wide variety of migrating groups including methyl, tert-butyl, cyclopropyl, vinyl, alkynyl, phenyl, and 2-furyl. A synthetically valuable feature is that a mixture of syn- and anti-epoxy alcohols affords only a single diastereoisomerically pure beta-hydroxy ketone. Additional advantages of the reaction include the presence in the product of two adjacent stereocenters and the efficient creation of a new quaternary center, valuable features in the synthesis of a variety of natural products.
• Substrate-Controlled Product Divergence: Conversion of CO₂ into Heterocyclic Products
  作者：Jeroen Rintjema、Roel Epping、Giulia Fiorani、Eddy Martín、Eduardo C. Escudero-Adán、Arjan W. Kleij

  DOI：10.1002/anie.201511521

  日期：2016.3.14

  Substituted epoxy alcohols and amines allow substrate‐controlled conversion of CO2 into a wide range of heterocyclic structures through different mechanistic manifolds. This new approach results in an unusual scope of CO2‐derived products by initial activation of CO2 through either the amine or alcohol unit, thus providing nucleophiles for intramolecular epoxy ring opening under mild reaction conditions

  取代的环氧醇和胺可通过不同的机械歧管，将底物控制的CO 2转化为多种杂环结构。这种新方法通过胺或醇单元对CO 2的初始活化，导致了源自CO 2衍生产品的异常范围，从而在温和的反应条件下为分子内环氧开环提供了亲核试剂。对照实验通过遵循S N i途径的亲核试剂开环步骤和5-exo-tet环化作用，支持了胺/醇片段在该过程中的关键作用，从而形成了杂环骨架。