threo-2-Acetamino-1.2-diphenyl-aethan-1-ol | 195625-08-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: threo-2-Acetamino-1.2-diphenyl-aethan-1-ol
• 英文别名: N-[(1R,2R)-2-hydroxy-1,2-diphenylethyl]acetamide
• CAS: 195625-08-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: QPBLBBVSBIWJJZ-HZPDHXFCSA-N

物化性质

• 沸点：
  478.5±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  threo-2-Acetamino-1.2-diphenyl-aethan-1-ol 在 phosphorus pentoxide 、 xylene 、 三氯氧磷 作用下， 生成 1-甲基-3-苯基异喹啉
  参考文献：
  名称：

  Kametani; Ohtsuki, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1955, vol. 75, p. 705,708

  摘要：

  DOI：
• 作为产物：
  描述：

  cis-2,3-diphenylaziridine 在 硫酸 、 苯 作用下， 生成 threo-2-Acetamino-1.2-diphenyl-aethan-1-ol
  参考文献：
  名称：

  Weissberger; Bach, Chemische Berichte, 1932, vol. 65, p. 631,635

  摘要：

  DOI：

文献信息

• Osmylated macroporous resins: safe, highly efficient and recyclable catalysts for asymmetric aminohydroxylation of olefinsElectronic supplementary information (ESI) available: experimental procedure. See http://www.rsc.org/suppdata/cc/b3/b303022a/
  作者：Cheon Hee Jo、Sien-Ho Han、Jung Woon Yang、Eun Joo Roh、Ueon-Sang Shin、Choong Eui Song

  DOI：10.1039/b303022a

  日期：2003.5.16

  Osmylated macroporous resins displayed excellent catalytic performances in the asymmetric aminohydroxylation of olefins and, moreover, these resins were easily recovered and reused without any significant decrease in catalytic efficiencies.

  锇化大孔树脂在烯烃的不对称氨基羟基化反应中表现出优异的催化性能，而且这些树脂易于回收和再利用，催化效率没有显着降低。
• USE OF ACYL MIGRATION IN SEPARATING DIASTEREOISOMERIC AMINO ALCOHOLS
  作者：GÁBOR FODOR、V. BRUCKNER、J. KISS、GÉZA ÓHEGYI

  DOI：10.1021/jo01155a001

  日期：1949.5
• Drefahl; Crahmer, Chemische Berichte, 1958, vol. 91, p. 745,749
  作者：Drefahl、Crahmer

  DOI：——

  日期：——
• N-Bromoacetamide—A New Nitrogen Source for the Catalytic Asymmetric Aminohydroxylation of Olefins
  作者：Milan Bruncko、Gunther Schlingloff、K. Barry Sharpless

  DOI：10.1002/anie.199714831

  日期：1997.8.4
• Bromination of alkenes in acetonitrile. A rate and product study
  作者：Giuseppe Bellucci、Roberto Bianchini、Cinzia Chiappe

  DOI：10.1021/jo00009a027

  日期：1991.4

  The reaction of simple alkenes and aryl alkenes with molecular bromine in damp MeCN occurred with solvent incorporation to give 2-bromo-1-(N-acetylamino)alkanes, 2-methyloxazolines, 2-acetoxyalkylamine hydrobromides, and 2-(N-acetylamino) alcohols. These products arose by the transformation of initially formed 2-bromo-1-(N-acetylamino)alkanes obtained by MeCN attack on bromonium or bromocarbonium ions to give nitrilium tribromide salts. These reacted with water to give 2-bromo-1-(N-acetylamino)alkanes. The kinetic profile of the reaction showed a very fast initial reaction of the alkene and Br2 to yield the nitrilium tribromide, followed by a much slower reaction of Br3- with the alkene. The incorporation of MeCN was Markovnikov and stereospecifically anti. The degree to which incorporation of solvent occurred depended upon the alkene structure and the initial reagent concentrations. A rationalization for the observed chemoselectivity and its dependence on the reaction conditions is offered.