1-(3-phenanthryl)ethanol | 84194-81-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 1-(3-phenanthryl)ethanol
• 英文别名: (1S)-1-phenanthren-3-ylethanol
• CAS: 84194-81-0
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: ZRWXPMQVCVDLPA-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-菲-3-基乙醇 生成 1-(3-phenanthryl)ethanol
  参考文献：
  名称：

  Enantioselective acylation of alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify the faster reacting enantiomer of an alcohol in this acylation

  摘要：

  Lipase QL-catalyzed acylation of secondary alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether gave preferentially the corresponding acetate with an R configuration. On the basis of the results, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a secondary alcohol reacts faster in this reaction. (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00186-3

文献信息

• Optical Resolution of 1-Arylethanols with a Condensed Aromatic Ring by Lipase from<i>Pseudomonas aeruginosa</i>
  作者：Katsuya Kato、Masato Katayama、Shozo Fujii、Hiroshi Kimoto

  DOI：10.1271/bbb.59.2178

  日期：1995.1

  Enantioselective syntheses of both enantiomers of l-arylethanols with a condensed aromatic ring have been done through acetylation of the racemic alcohols with vinyl acetate in the presence of a lipase from Pseudomonas aeruginosa (Toyobo, LIP). The lipase LIP showed high enantioselectivity and reactivity for the title compounds, reacted acetates, and remaining alcohols were obtained with high optical purity.

  在铜绿假单胞菌（Toyobo，LIP）的脂肪酶存在下，通过用乙酸乙烯酯乙酰化外消旋醇，完成了具有稠合芳环的 L-芳基乙醇的两种对映体的对映选择性合成。脂肪酶 LIP 对标题化合物、反应的乙酸酯和剩余的醇表现出高光学纯度的高对映选择性和反应性。
• Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00429-6

  日期：1996.11

  Lipase QL (from Alcaligenes sp.)-catalyzed acylation of alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether converted preferentially primary alcohols with an S configuration and secondary alcohols with an R configuration into the corresponding homochiral acetates. On the basis of observed enantiomer selectivities, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a primary or a secondary alcohol reacts faster in this acylation. Copyright (C) 1996 Published by Elsevier Science Ltd
• Microbially mediated enantioselective ester hydrolyses utilizing Rhizopus nigricans. A new method of assigning the absolute stereochemistry of acyclic 1-arylalkanols
  作者：Herman Ziffer、Kenichi Kawai、Masaji Kasai、Mitsuru Imuta、Cleanthis Froussios

  DOI：10.1021/jo00166a016

  日期：1983.9
• KASAI, MASAJI;FROUSSIOS, C.;ZIFFER, H., J. ORG. CHEM., 1983, 48, N 4, 459-464
  作者：KASAI, MASAJI、FROUSSIOS, C.、ZIFFER, H.

  DOI：——

  日期：——
• Enantioselective acylation of alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify the faster reacting enantiomer of an alcohol in this acylation
  作者：Koichiro Naemura、Masaki Murata、Rie Tanaka、Masashi Yano、Keiji Hirose、Yoshito Tobe

  DOI：10.1016/0957-4166(96)00186-3

  日期：1996.6

  Lipase QL-catalyzed acylation of secondary alcohols using isopropenyl acetate as the acylating agent in diisopropyl ether gave preferentially the corresponding acetate with an R configuration. On the basis of the results, a predictive active site model for lipase QL is proposed for identifying which enantiomer of a secondary alcohol reacts faster in this reaction. (C) 1996 Elsevier Science Ltd