2-(1-Hexamethyleneimino)-1-phenylethanol | 4641-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环庚烷
• 英文名称: 2-(1-Hexamethyleneimino)-1-phenylethanol
• 英文别名: 2-(hexahydroazepin-1-yl)-1-phenylethanol；2-(Perhydro-1-azeinyl)-1-phenylethanol；2-(azepan-1-yl)-1-phenylethanol；2-hexahydroazepin-1-yl-1-phenyl-ethanol；2-Hexahydroazepin-1-yl-1-phenyl-aethanol；1-Phenyl-2-hexamethylenimino-ethanol-(1)
• CAS: 4641-52-5
• 化学式: C₁₄H₂₁NO
• mdl: MFCD01117940
• 分子量: 219.327
• InChiKey: CCWFMRDERJDZCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.571
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1-Hexamethyleneimino)-1-phenylethanol 在 edetate disodium 、 mercury(II) oxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以100%的产率得到1-(2-Hydroxy-2-phenylethyl)perhydro-2-azepinon
  参考文献：
  名称：

  Moehre, H.; Kamper, Ch., Pharmazie, 1983, vol. 38, # 8, p. 512 - 520

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(2-Hydroxy-2-phenylethyl)perhydro-2-azepinon 在 甲酸 作用下， 以 盐酸 、 水 为溶剂， 反应 5.0h， 生成 2-(1-Hexamethyleneimino)-1-phenylethanol
  参考文献：
  名称：

  Moehre, H.; Kamper, Ch., Pharmazie, 1983, vol. 38, # 8, p. 512 - 520

  摘要：

  DOI：

文献信息

• Dehydrierung cyclischer tertiärer Amine unter Reaktionsbeteiligung von enantiomeren nucleophilen Nachbargruppen / Dehydrogenation of Cyclic Tertiary Amines with Neighbouring of Enantiomeric Nucleophiles
  作者：Hans Möhrle、Thomas Berkenkemper

  DOI：10.1515/znb-2002-0409

  日期：2002.4.1

  For stereochemical investigation of their dehydrogenation, the enantiomers of the aminoalcohols 1, 2, and 3 were prepared from optically active sources, while the enantiomers of the diamines 8 and 9 were available by resolution of the racemates.T he pure antipodes of 1, 2, and 3 reacted with mercury(II)-EDTA by a twofold dehydrogenation via intermediate participation of the neighbouring alcoholic group to the optically active lactams 5, 6, and 7 under complete retention of configuration.In the same manner the diamines 8 and 9 generated by four electron withdrawal the cycloamidines 10 and 11.

  为了对它们的脱氢进行立体化学研究，氨基醇1、2和3的对映体是从光学活性源制备而来的，而二胺8和9的对映体则通过分离外消旋体获得。化合物1、2和3的纯对映体通过邻近醇基的中间参与，通过汞(II)-EDTA的双重脱氢反应生成了光学活性内酰胺5、6和7，保持构型完全不变。同样地，通过四电子提取生成了环酰胺10和11的二胺8和9。
• Blicke; Johnson, Journal of the American Pharmaceutical Association (1912), 1956, vol. 45, p. 440
  作者：Blicke、Johnson

  DOI：——

  日期：——
• Borrowing Hydrogen Methodology for Amine Synthesis under Solvent-Free Microwave Conditions
  作者：Andrew J. A. Watson、Aoife C. Maxwell、Jonathan M. J. Williams

  DOI：10.1021/jo102521a

  日期：2011.4.1

  Application of microwave heating to the Borrowing Hydrogen strategy to form C-N bonds from alcohols and amines is presented, removing the need for solvent and reducing the reaction times while still yielding results comparable with those using thermal heating.
• Aminophenylethanols and Related Compounds
  作者：Seymour L. Shapiro、Harold Soloway、Louis Freedman

  DOI：10.1021/ja01555a042

  日期：1958.11
• Boranes in Synthesis. 6. A New Synthesis of .beta.-Amino Alcohols from Epoxides. Use of Lithium Amides and Aminoborane Catalysts To Synthesize .beta.-Amino Alcohols from Terminal and Internal Epoxides in High Yield
  作者：Clifford E. Harris、Gary B. Fisher、David Beardsley、Lawrence Lee、Christian T. Goralski、Lawrence W. Nicholson、Bakthan Singaram

  DOI：10.1021/jo00104a034

  日期：1994.12

  A study of the conversion of terminal and internal epoxides to the corresponding beta-amino alcohols using simple primary and secondary lithium amides has been carried out. Thus, styrene oxide and 1,2-epoxydodecane react directly with primary and secondary lithium amides in THF at 25 degrees C to give a single regioisomer of the corresponding beta-amino alcohols in 80-100% isolated yields. Since internal epoxides are known to yield predominantly allylic alcohols when reacted with lithium amides, we employed a series of aminoborane Lewis-acid catalysts, generated in situ, to suppress formation of the allylic alcohols. Thus, the reaction of cyclohexene oxide with a variety of primary and secondary lithium amides at 34 degrees C in diethyl ether in the presence of a catalytic amount of B-bromo-9-BBN afforded the corresponding beta-amino alcohols in 70-95% isolated yield.