cis-4-chloro-2,6-dicyclohexyltetrahydro-2H-pyran | 123464-12-0

• 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: cis-4-chloro-2,6-dicyclohexyltetrahydro-2H-pyran
• 英文别名: 4-chloro-2,6-dicyclohexyltetrahydro-2H-pyran；cis-4-chloro-2,6-dicyclohexyltetrahydropyran
• CAS: 123464-12-0
• 化学式: C₁₇H₂₉ClO
• 分子量: 284.87
• InChiKey: BTIMAJGFYBQIRN-OSYLJGHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  1.0
• 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：

  chloro-dimethyl-(1-phenylethoxy)silane 在 三氯化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 7.0h， 生成 cis-4-chloro-2,6-dicyclohexyltetrahydro-2H-pyran
  参考文献：
  名称：

  Lewis acid-promoted condensation of allylalkoxysilanes with carbonyl compounds. Synthesis of tetrahydropyrans

  摘要：

  DOI：

  10.1021/jo00285a025

文献信息

• Chemoselective three-component synthesis of homoallylic azides using an FeCl3 catalyst
  作者：Suman Pramanik、Prasanta Ghorai

  DOI：10.1039/c3ra42821d

  日期：——

  A one-pot, three-component synthesis of homoallylic azides from corresponding aldehydes, TMS-allyl, and TMS-N3 has been developed for the first time using an FeCl3 catalyst. The aromatic and hetero-aromatic aldehydes provided the corresponding homoallylic azides with excellent chemoselectivity. This direct azido-allylation process is also readily scalable (1–28 mmol). The mechanism of the process is proposed. Finally, the selective as well as simultaneous functionalization of homoallylic azides has also been exemplified.

  首次开发了一种使用FeCl3催化剂的一锅法三组分合成同烯丙基叠氮化合物，原料为相应的醛、TMS-烯丙基和TMS-N3。芳香醛和杂芳香醛提供了相应的同烯丙基叠氮化合物，具有优异的化学选择性。这种直接的叠氮-烯丙基化反应也能够很容易地放大到1～28毫摩尔规模。提出了该反应的机理。最后，还举例说明了同烯丙基叠氮化合物的选择性和同时功能化。
• An Efficient Prins Cyclization for Stereoselective Synthesis of Tetrahydropyran from Imines and Homoallyl Alcohols
  作者：Congrong Liu、Daojuan Cheng、Fulai Yang

  DOI：10.1002/cjoc.201400450

  日期：2014.11

  An unprecedented protocol has been developed for the efficient synthesis of substituted tetrahydropyrans via a bismuth‐promoted Prins cyclization of imines with homoallyl alcohols. In the presence of 40 mol% BiCl3, a wide variety of imines react smoothly with homoallyl alcohols at room temperature to give the corresponding 4‐chlorotetrahydropyran derivatives in good to excellent yields.

  已经开发出了一种空前的方案，用于通过铋促进的Prins与高烯丙醇对亚胺的Prins环化反应来高效合成取代的四氢吡喃。在40 mol％BiCl 3的存在下，各种各样的亚胺在室温下与均烯丙基醇平稳反应，以良好的收率得到相应的4-氯四氢吡喃衍生物。
• Green chemistry: solvent- and metal-free Prins cyclization. Application to sequential reactions
  作者：Damien Clarisse、Béatrice Pelotier、Olivier Piva、Fabienne Fache

  DOI：10.1039/c1cc16501a

  日期：——

  Prins cyclization between a homoallylic alcohol and an aldehyde, promoted by trimethylsilyl halide, afforded 4-halo-tetrahydropyrans with good to excellent yields. Thanks to the absence of the solvent and metal, the THP thus obtained have been implicated without purification in several other reactions, in a sequential way, affording in particular new indole derivatives.

  普林斯环化反应在一个同烯醇和醛的作用下，通过三甲基氯硅烷催化，得到四氢吡喃的4-卤代衍生物，产率良好至优良。由于没有溶剂和金属，因此得到的THP可以不经过纯化，直接在几种其他反应中顺序使用，特别是获得了新的吲哚衍生物。
• Prins Cyclization Catalyzed by a Fe ^III /Trimethylsilyl Halide System: The Oxocarbenium Ion Pathway versus the [2+2] Cycloaddition
  作者：Sixto J. Pérez、Martín Purino、Pedro O. Miranda、Víctor S. Martín、Israel Fernández、Juan I. Padrón

  DOI：10.1002/chem.201502488

  日期：2015.10.19

  iron(III)‐catalyzed Prins cyclization reaction between homoallylic alcohols and non‐activated alkenes, two mechanistic pathways can be envisaged, namely the classical oxocarbenium route and the alternative [2+2] cycloaddition‐based pathway. It is found that the [2+2] pathway is disfavored for those alcohols having non‐activated and non‐substituted alkenes. In these cases, the classical pathway, via

  通过联合实验-计算研究，探索了控制铁（III）盐催化链烯烃Prins环化的不同因素。铁（III）盐/三甲基甲硅烷基卤化物体系已被证明是合成交叉顺式的极好促进剂双取代四氢吡喃，可最大程度地减少侧链交换衍生产物的形成。在这种铁（III）催化的均丙醇与非活化烯烃之间的Prins环化反应中，可以设想两种机理途径，即经典的氧碳鎓途径和替代的[2 + 2]基于环加成的途径。发现对于具有未活化和未取代的烯烃的那些醇而言，[​​2 + 2]途径是不利的。在这些情况下，首选通过关键氧碳鎓离子的经典途径。此外，最终产物的分布在很大程度上取决于均丙醇中与羟基相邻的取代基的性质，该取代基可促进或阻碍2-氧代-邻位双侧重排。
• Suppression of epimerization due to selectivity leakage: an application towards the total synthesis of (−)-centrolobine
  作者：Cheng-Hsia Angeline Lee、Teck-Peng Loh

  DOI：10.1016/j.tetlet.2005.12.108

  日期：2006.3

  An InCl3-mediated Prins cyclization of homoallylic alcohols with aldehydes has been established. The enantioselectivities of the trisubstituted tetrahydropyrans are almost retained through the suppression of epimerization. The synthetic value of this protocol is demonstrated by the total synthesis of (−)-centrolobine.

  已经建立了InCl 3介导的均醛醇与醛的Prins环化。三取代的四氢吡喃的对映选择性几乎通过抑制差向异构而得以保留。该协议的合成价值通过（-）-中心洛宾的全合成得到证明。