1-cyano-2-(1-naphthoxy)ethanol | 80789-63-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-cyano-2-(1-naphthoxy)ethanol
• 英文别名: α-naphthyloxyacetaldehyde cyanohydrin；(+/-)-2-hydroxy-3-naphthoxypropanenitrile；2-Hydroxy-3-(1-naphthoxy)-propannitril；Oppqgdxhvlriaj-uhfffaoysa-；2-hydroxy-3-naphthalen-1-yloxypropanenitrile
• CAS: 80789-63-5
• 化学式: C₁₃H₁₁NO₂
• 分子量: 213.236
• InChiKey: OPPQGDXHVLRIAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  456.8±30.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-cyano-2-(1-naphthoxy)ethanol 在 氢氧化钾 、 硼烷四氢呋喃络合物 、 水 、 氢溴酸 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 48.5h， 生成 (S)-3-(萘-1-氧基)丙烷-1,2-二醇
  参考文献：
  名称：

  Absolute configuration of glycerol derivatives. 8. 2-Hydroxy-3-(1-naphthoxy)propionic acid, a major oxidative metabolite of the .beta.-adrenergic antagonist propranolol

  摘要：

  DOI：

  10.1021/jo00347a042
• 作为产物：
  描述：

  2-萘-1-氧基乙醛 生成 1-cyano-2-(1-naphthoxy)ethanol
  参考文献：
  名称：

  Lipase-catalyzed irreversible transesterification using enol esters: Resolution of cyanohydrins and syntheses of ethyl (R)-2-hydroxy-4-phenylbutyrate and (S)-propranolol

  摘要：

  DOI：

  10.1016/s0040-4039(00)99613-8

文献信息

• Ohta, Hiromichi; Miyamae, Yoshitaka; Tsuchihashi, Gen-ichi, Agricultural and Biological Chemistry, 1989, vol. 53, # 1, p. 215 - 222
  作者：Ohta, Hiromichi、Miyamae, Yoshitaka、Tsuchihashi, Gen-ichi

  DOI：——

  日期：——
• Enzymatic synthesis of (R)-cyanohydrins by three (R)-oxynitrilase sources in micro-aqueous organic medium
  作者：Guoqiang Lin、Shiqing Han、Zuyi Li

  DOI：10.1016/s0040-4020(98)01160-0

  日期：1999.3

  The enantioselective synthesis of optically active (R)-cyanohydrins generated from several aromatic, heteroaromatic and aliphatic aldehydes and methyl ketones was carried out using almond. peach or loquat meal as (R)-oxynitrilase sources in diisopropyl ether under micro-aqueous conditions. The micro-aqueous reaction system, which is superior to the conventionally used water-organic biphase reaction system, performed well over the temperature range of 4 degrees C to 30 degrees C. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Aminoalkohole, 2. Mitt.: Ein Verfahren zur Herstellung enantiomerenreiner pharmakologisch aktiver ?-Aminoalkohole
  作者：C. R. Noe、M. Knollm�ller、P. G�rtner、W. Fleischhacker、E. Katikarides

  DOI：10.1007/bf00813211

  日期：1995.4

  A synthesis of beta-aminoalcohols is described starting from racemic or enantiomerically pure alpha-hydroxynitriles which were O-protected using enantiomerically pure acetal type protective groups. Reduction with lithium aluminium hydride yielded O-protected beta-aminoalcohols. Whenever diastereomeric O-protected cyanohydrins could not be separated, the mixture was reduced and the resulting O-protected aminoalcohols were separated. Removal of the protective group using hydrogen chloride and methanol yielded enantiomerically pure beta-aminoalcohols or their corresponding hydrochlorides.
• GOUNTZOS H.; JACKSON W. R.; HARRINGTON K. J., AUSTRAL. J. CHEM., 39,(1986) N 7, 1135-1140
  作者：GOUNTZOS H.、 JACKSON W. R.、 HARRINGTON K. J.

  DOI：——

  日期：——
• Lipase-catalyzed irreversible transesterification using enol esters: Resolution of cyanohydrins and syntheses of ethyl (R)-2-hydroxy-4-phenylbutyrate and (S)-propranolol
  作者：Yi-Fong Wang、Shui-Tein Chen、Kevin K.-C. Liu、Chi-Huey Wong

  DOI：10.1016/s0040-4039(00)99613-8

  日期：1989.1

表征谱图