(2S,3R)-3-bromotetrahydro-2-phenyl-2H-pyran | 81991-71-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (2S,3R)-3-bromotetrahydro-2-phenyl-2H-pyran
• 英文别名: trans-3-Brom-2-phenyltetrahydropyran；(2S,3R)-3-bromo-2-phenyloxane
• CAS: 81991-71-1
• 化学式: C₁₁H₁₃BrO
• 分子量: 241.128
• InChiKey: VNSXJZZRPWDLFL-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-苯基戊-4-烯基-1-醇 在 N-溴代丁二酰亚胺(NBS) 、 O-[(S)-[(2R,4S,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methyl] N-(2,4-dimethoxyphenyl)carbamothioate 作用下， 以 氯仿 、 甲苯 为溶剂， 生成 (2S,3R)-3-bromotetrahydro-2-phenyl-2H-pyran
  参考文献：
  名称：

  氨基硫代氨基甲酸酯催化的1,2-二取代烯烃酸的不对称溴内酯化

  摘要：

  已经开发出使用氨基-硫代氨基甲酸酯催化剂对1，2-二取代的烯烃进行有效和对映选择性的溴内酯化，从而形成了包含两个手性中心的δ-内酯，产率高达99％，ee为95％。

  DOI：

  10.1021/ol200840e

文献信息

• Enantioselective Bromocycloetherification by Lewis Base/Chiral Brønsted Acid Cooperative Catalysis
  作者：Scott E. Denmark、Matthew T. Burk

  DOI：10.1021/ol203033k

  日期：2012.1.6

  A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Brønsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpentenols to form bromomethyltetrahydrofurans. The constitutional site selectivity is highly dependent upon the aromatic substituent and the configuration

  描述了用于 5-芳基戊烯醇的对映选择性溴环醚化的二元催化剂体系。非手性路易斯碱和手性布朗斯台德酸的组合为Z配置的 5-芳基戊烯醇环化形成溴甲基四氢呋喃提供了良好的对映选择性。结构位点选择性高度依赖于芳族取代基和双键的构型。
• Development and Mechanism of an Enantioselective Bromocycloetherification Reaction via Lewis Base/Chiral Brønsted Acid Cooperative Catalysis
  作者：Scott E. Denmark、Matthew T. Burk

  DOI：10.1002/chir.22259

  日期：2014.7

  The development of a binary catalyst system for bromocycloetherification, consisting of an achiral Lewis base and a chiral Brønsted acid, is described in detail. The results of preliminary kinetic studies are also presented. Chirality 26:343–354, 2013. © 2013 Wiley Periodicals, Inc.

  详细描述了由非手性路易斯碱和手性布朗斯台德酸组成的溴环醚化二元催化剂体系的开发。还提供了初步动力学研究的结果。手性 26：343–354，2013 年。© 2013 威利期刊公司。
• Enantioselective Bromocyclization of Olefins Catalyzed by Chiral Phosphoric Acid
  作者：Deshun Huang、Haining Wang、Fazhen Xue、Huan Guan、Lijun Li、Xianyou Peng、Yian Shi

  DOI：10.1021/ol202527g

  日期：2011.12.16

  A chiral phosphoric acid catalyzed enantioselective bromocyclization of olefins is described. Various cis-, trans-, or trisubstituted γ-hydroxy-alkenes and γ-amino-alkenes can cyclize under the reaction conditions to give optically active 2-substituted tetrahydrofurans and tetrahydropyrroles in up to 91% ee.

  描述了手性磷酸催化的烯烃的对映选择性溴环化。各种顺式，反式或三取代的γ-羟基烯烃和γ-氨基烯烃可以在反应条件下环化，得到光学活性的2-取代的四氢呋喃和四氢吡咯，其ee含量高达91％。
• Lewis base catalysis of bromo- and iodolactonization, and cycloetherification
  作者：Scott E. Denmark、Matthew T. Burk

  DOI：10.1073/pnas.1005296107

  日期：2010.11.30

  Lewis base catalyzed bromo- and iodolactonization reactions have been developed and the effects of catalyst structure on rate and cyclization selectivity have been systematically explored. The effects of substrate structure on halolactonization reactions and the interaction of those effects with the effects of catalyst structure have been investigated, leading to synthetically useful improvements in cyclization selectivity. The knowledge acquired was applied to the development of Lewis base catalyzed bromo- and iodocycloetherification reactions. The ability of some of the surveyed catalysts to influence the cyclization selectivity of halolactonization reactions demonstrates their presence in the transition structure of the product-determining cyclization step. This observation implies that chiral derivatives of these catalysts have the potential to provide enantioenriched products regardless of the rates or mechanisms of halonium ion racemization.

  通过发展路易斯碱催化的溴和碘内酯化反应，系统地探索了催化剂结构对反应速率和环化选择性的影响。研究了底物结构对卤代内酯化反应的影响以及这些影响与催化剂结构影响的相互作用，从而在环化选择性方面实现了合成上的有用改进。所获得的知识被应用于发展路易斯碱催化的溴和碘环醚化反应。一些调查的催化剂影响卤代内酯化反应的环化选择性，表明它们存在于产物决定的环化步骤的过渡结构中。这种观察意味着这些催化剂的手性衍生物有潜力提供对映富集的产物，无论卤化离子旋转的速率或机制如何。