4-bromo-2,6-diphenyl-tetrahydro-2H-pyran | 111268-67-8

• 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: 4-bromo-2,6-diphenyl-tetrahydro-2H-pyran
• 英文别名: 4-bromo-tetrahydro-2,6-diphenyl-2H-pyran；4-bromo-2,6-diphenyltetrahydro-2H-pyran；4-bromo-2,6-diphenyltetrahydropyran
• CAS: 111268-67-8
• 化学式: C₁₇H₁₇BrO
• 分子量: 317.225
• InChiKey: YWYKWBLYGRAHOJ-OSYLJGHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.04
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  苯甲醛 在 aluminum (III) chloride 、 tin(II) chloride dihdyrate 、 溴化锡 、 potassium iodide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 4.0h， 生成 4-bromo-2,6-diphenyl-tetrahydro-2H-pyran
  参考文献：
  名称：

  顺式-2,6-二苯基-4-羟基四氢吡喃及其类似物的非对映选择性合成通过 Prins 环化、晶体结构测定和理论研究

  摘要：

  摘要 我们在本文中报道了四氢吡喃基衍生物 1-5 的非对映选择性合成，通过光谱学确定其顺式构型，最后明确显示 1-5 构型及其晶体堆积特征的晶体结构测定。除此之外，我们还利用密度泛函理论 (M06-2X/6-311++G**) 开展了一项理论研究，以获得气相中 1-5 个优化的分子几何形状。

  DOI：

  10.1016/j.molstruc.2012.11.044

文献信息

• Synthesis of a novel diarylheptanoid isolated from Zingiber officinale
  作者：Gregory D. Parker、Peter T. Seden、Christine L. Willis

  DOI：10.1016/j.tetlet.2009.03.154

  日期：2009.7

  Syntheses of 4-acetoxy-2,6-disubstituted tetrahydropyrans via Prins cyclisation of homoallylic alcohols with benzylic aldehydes are described and the methodology is applied in the total synthesis of diarylheptanoid 1 confirming both the structure and absolute configuration of the natural product.

  描述了通过均芳醇与苄基醛的Prins环化来合成4-乙酰氧基-2,6-二取代的四氢吡喃，并将该方法应用于二芳基庚烷1的全合成中，从而确认了天然产物的结构和绝对构型。
• The Role Ionic Liquid [BMIM][PF6] in One-Pot Synthesis of Tetrahydropyran Rings through Tandem Barbier–Prins Reaction
  作者：Poliane K. Batista、João Marcos G. de O. Ferreira、Fabio P. L. Silva、Mario L. A. A Vasconcellos、Juliana A. Vale

  DOI：10.3390/molecules24112084

  日期：——

  aldehydes. The use of [BMIM][PF6] gave Prins products from several aldehydes in good yields and reaction times. We also found that the anion, PF6-, accelerates the Barbier reaction when used alone, and the excess SnBr2 from the reaction conditions of the Barbier reaction leads to the formation of the THP rings, thus acting as a catalyst for Prins cyclization. Additionally, we demonstrate that ionic

  四氢吡喃 (THP) 环在几种天然产物中很常见，因此，正在开发各种策略来合成这些环。本工作描述了由离子液体 1-丁基-3-甲基咪唑鎓六氟磷酸盐 [BMIM][PF6] 通过烯丙基溴之间的 Barbier-Prins 反应促进的 2,4,6-三取代四氢吡喃化合物的一锅合成研究。和醛类。使用 [BMIM][PF6] 以良好的产率和反应时间从几种醛中得到 Prins 产品。我们还发现阴离子 PF6- 在单独使用时会加速 Barbier 反应，而 Barbier 反应条件下过量的 SnBr2 会导致 THP 环的形成，从而作为 Prins 环化的催化剂。此外，
• Synthesis of 4-halotetrahydropyrans from allylsilanes and carbonyl compounds in the presence of lewis acids
  作者：Laura Coppi、Alfredo Ricci、Maurizio Taddei

  DOI：10.1016/s0040-4039(00)95890-8

  日期：1987.1

  An unexpected behavior of the reaction of allylsilanes and carbonylcompounds allowed the stereospecific preparation of differently substituted 4-halotetrahydropyrans with an “all cis” configuration.

  烯丙基硅烷与羰基化合物反应的出乎意料的行为允许立体异构地制备具有“全顺式”构型的不同取代的4-卤代四氢吡喃。
• One-pot allyl-/crotylboration-Prins cyclization of aldehydes
  作者：P. Veeraraghavan Ramachandran、Pravin D. Gagare

  DOI：10.1016/j.tetlet.2011.06.043

  日期：2011.8

  Multi-substituted tetrahydropyrans (THPs) have been prepared via a one-pot, In(OTf)(3)-catalyzed, sequential allyl-/crotylboration-Prins cyclization. The homoallylic borate intermediate formed during the allyl- and crotylboration was converted in situ to an oxocarbenium ion and trapped with a nucleophile. The reaction has been extended to include a one-pot allylboration-cross Prins cyclization as well. (C) 2011 Published by Elsevier Ltd.
• Synthesis of (−)-Centrolobine by Prins Cyclizations that Avoid Racemization
  作者：Shinji Marumoto、James J. Jaber、Justin P. Vitale、Scott D. Rychnovsky

  DOI：10.1021/ol026751i

  日期：2002.10.1

  [GRAPHICS]The segment-coupling Prins cyclization avoids two of the problems common to other Prins cyclization protocols: side-chain exchange and partial racemization by reversible 2-oxonia Cope rearrangement. Model studies demonstrate the stereochemical fidelity of Prins cyclizations using alpha-acetoxy ethers compared with direct aldehyde-alcohol Prins reactions. Furthermore, we propose a mechanism for the racemization observed in some intermolecular Prins cyclizations. Two straightforward syntheses of optically pure (-)-centrolobine highlight the utility of Prins cyclizations.