(1-(phenylamino)cyclohexyl)methanol | 92195-94-3

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (1-(phenylamino)cyclohexyl)methanol
• 英文别名: 1-anilinocyclohexanemethanol；1-Anilino-1-hydroxymethyl-cyclohexan；[1-(Phenylamino)cyclohexyl]methanol；(1-anilinocyclohexyl)methanol
• CAS: 92195-94-3
• 化学式: C₁₃H₁₉NO
• 分子量: 205.3
• InChiKey: OCCMCBXSULYDIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1-(phenylamino)cyclohexyl)methanol 在 吡啶盐酸盐 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 1-phenyl-3-oxa-1-azaspiro[4.5]decan-2-one
  参考文献：
  名称：

  Dual Brønsted Acid/Nucleophilic Activation of Carbonylimidazole Derivatives

  摘要：

  Carbonylimidazole derivatives have been found to be highly active acylation reagents for esterification and amidation in the presence of pyridinium salts. These reactions are thought to involve both Bronsted acid and nucleophilic catalysis. This mode of activation has been applied to the synthesis of difficult to access oxazolidinones, as well as esters and amides. Finally, the use of pyridinium salts has been shown to accelerate the esterification of carboxylic acids with imidazole carbamates.

  DOI：

  10.1021/ol300339q
• 作为产物：
  描述：

  N-[1-(氨基甲基)环己基]苯胺 在 盐酸 、 sodium nitrite 作用下， 反应 0.5h， 生成 (1-(phenylamino)cyclohexyl)methanol
  参考文献：
  名称：

  Studies on Organophosphorus Compounds: The Synthesis of [1,3,2]-Diazaphospholes and [1,3,2]-Oxaazaphospholes

  摘要：

  A number of spiro[cyclopentane (cyclohexane, and cycloheptane)-1,4'-perhydro-[1,3,2]diazaphosphole] derivatives (3a-c, 5a-c, 11a-c, and 12a-c) and spiro-[cyclopentane (cyclohexane, and cycloheptane)-1,4'-perhydro[1,3,2]oxaazaphos-phole] derivatives (7a-c) were prepared via an interaction of 2,4-bis-(4-methoxy-phenyl)-1,3,2,4-dithiaphosphetane-2,4-disulphide (1) with substances containing two functional groups.

  DOI：

  10.1080/10426500600754794

文献信息

• The Acrylamide Moiety as an Activated Alkene Component in the Intramolecular Baylis-Hillman Reaction: Facile Synthesis of Functionalized α-Methylene Lactam and Spirolactam Frameworks
  作者：Deevi Basavaiah、Guddeti Chandrashekar Reddy、Kishor Chandra Bharadwaj

  DOI：10.1002/ejoc.201301526

  日期：2014.2

  A facile strategy for the intramolecular Baylis–Hillman reaction by utilizing an acrylamide moiety as an activated alkene component was developed, which thus provides a convenient protocol for obtaining five- and six-membered α-methylene lactam and spirolactam derivatives.

  开发了一种利用丙烯酰胺部分作为活化烯烃组分进行分子内 Baylis-Hillman 反应的简便策略，从而为获得五元和六元 α-亚甲基内酰胺和螺内酰胺衍生物提供了方便的方案。
• Substituted spirocyclic inhibitors of autotaxin
  申请人：X-Rx, Inc.

  公开号：US10011601B2

  公开（公告）日：2018-07-03

  The present invention relates to compounds according to Formula 1 and pharmaceutically acceptable salts, synthesis, intermediates, formulations, and methods of disease treatment therewith, including cancer, lymphocyte homing, chronic inflammation, neuropathic pain, fibrotic diseases, thrombosis, and cholestatic pruritus, mediated at least in part by ATX.

  本发明涉及根据式 1 的化合物和药学上可接受的盐、合成、中间体、制剂以及用其治疗疾病的方法，包括至少部分由 ATX 介导的癌症、淋巴细胞归巢、慢性炎症、神经性疼痛、纤维化疾病、血栓形成和胆汁淤积性瘙痒症。
• Free-radical hydroxymethylation of ketimines generated in situ: a one-pot multicomponent synthesis of β,β-disubstituted-β-aminoalcohols
  作者：Bianca Rossi、Nadia Pastori、Angelo Clerici、Carlo Punta

  DOI：10.1016/j.tet.2012.09.107

  日期：2012.12

  We report how an acidic TiCl4-Zn/t-BuOOH system is able to promote the one-pot multicomponent synthesis of beta,beta-disubstituted-beta-aminoalcohols via nucleophilic addition of a hydroxymethyl radical to activated ketimines generated in situ in methanol solvent. While ketimines are generally recognized as less reactive and less stable when compared with aldimines, Ti(IV) plays a key role in facilitating their formation and in enhancing their electrophilic character. As a consequence, the reaction occurs at room temperature and under non-anhydrous conditions in just 1 h, without requiring either the preformation of the ketimine or protection of the amino group. The scope of the reaction is widely explored and a possible mechanism is discussed. (C) 2012 Elsevier Ltd. All rights reserved.