cyclohexyl(phenyl)(pyridin-2-yl)methanol | 109253-36-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: cyclohexyl(phenyl)(pyridin-2-yl)methanol
• 英文别名: α-cyclohexyl-α-phenyl-2-pyridinemethanol；Cyclohexyl-phenyl-[2]pyridyl-methanol；Cyclohexyl-phenyl-pyridin-2-ylmethanol
• CAS: 109253-36-3
• 化学式: C₁₈H₂₁NO
• 分子量: 267.371
• InChiKey: UCCZXLDDKIVAFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(cyclohexyl(phenyl)methoxy)pyridine 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以20%的产率得到cyclohexyl(phenyl)(pyridin-2-yl)methanol
  参考文献：
  名称：

  [1,2] -2-苄氧基吡啶和相关吡啶基醚的阴离子重排

  摘要：

  描述了2-苄氧基吡啶的阴离子重排。苄基碳的吡啶定向金属化反应通过假定的缔合机制（加成/消除）导致吡啶发生1，2-迁移。以高收率获得了几种芳基吡啶基甲醇。从这种方法学中可以得出一种正式的合成方法，即用于治疗季节性过敏和花粉症的抗组胺药卡宾沙明。

  DOI：

  10.1021/jo901707x

文献信息

• Photoredox and NHC Enabled Deoxygenative Alcohol Homologation via Formal 1,2-Addition
  作者：Shuo Song、Zhongxian Li、Lele Wang、Tianlong Zeng、Qiang Hu、Jun Zhu

  DOI：10.1021/acs.orglett.3c03857

  日期：2024.1.12

  A highly efficient photoinduced iron-catalyzed method has been developed for the direct use of alcohols as surrogates for organometallic reagents in the synthesis of tertiary alcohols. This method can be applied to both primary and secondary alcohols with diverse structures, enabling their reaction with aryl ketones under mild conditions. A variety of functional groups, including those that are typically

  开发了一种高效的光诱导铁催化方法，可直接使用醇作为有机金属试剂的替代物来合成叔醇。该方法适用于不同结构的伯醇和仲醇，使其能够在温和的条件下与芳基酮发生反应。多种官能团，包括那些在常规叔醇合成条件下通常具有反应性的官能团，是相容的。从机理上讲，该反应是通过自由基直接加成到羰基途径来进行的。
• Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation–Deuteration of Heterobenzylic Methylenes
  作者：Yonghai Liu、Yang Yu、Chengyu Sun、Yiwei Fu、Zhiguo Mang、Lei Shi、Hao Li

  DOI：10.1021/acs.orglett.0c03108

  日期：2020.10.16

  We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.
• Central Stimulants. α,α-Disubstituted 2-Piperidinemethanols and 1,1-Disubstituted Heptahydroöxazolo [3,4-a]pyridines
  作者：Frederick J. McCarty、Charles H. Tilford、M. G. Van Campen

  DOI：10.1021/ja01559a066

  日期：1957.1
• BOJADZIEV, S.;TSANKOV, D.;IVANOV, P.;BEROVA, N., IZV. XIM./BLG. AN, 21,(1988) N 2, 201-207
  作者：BOJADZIEV, S.、TSANKOV, D.、IVANOV, P.、BEROVA, N.

  DOI：——

  日期：——
• [1,2]-Anionic Rearrangement of 2-Benzyloxypyridine and Related Pyridyl Ethers
  作者：Jingyue Yang、Gregory B. Dudley

  DOI：10.1021/jo901707x

  日期：2009.10.16

  An anionic rearrangement of 2-benzyloxypyridine is described. Pyridine-directed metalation of the benzylic carbon leads to 1,2-migration of pyridine via a postulated associative mechanism (addition/elimination). Several aryl pyridyl carbinols were obtained in high yields. A formal synthesis of carbinoxamine, an antihistamine drug used for the treatment of seasonal allergies and hay fever, emerges from

  描述了2-苄氧基吡啶的阴离子重排。苄基碳的吡啶定向金属化反应通过假定的缔合机制（加成/消除）导致吡啶发生1，2-迁移。以高收率获得了几种芳基吡啶基甲醇。从这种方法学中可以得出一种正式的合成方法，即用于治疗季节性过敏和花粉症的抗组胺药卡宾沙明。