2-(1,2,3,4-四氢异喹啉-1-基)-1-萘酚 | 897035-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 2-(1,2,3,4-四氢异喹啉-1-基)-1-萘酚
• 英文名称: 1-(α-hydroxy-2-naphthyl)-1,2,3,4-tetrahydroisoqinoline
• 英文别名: 2-(1,2,3,4-tetrahydroisoquinolin-1-yl)naphthalen-1-ol；2-(1,2,3,4-tetrahydro-isoquinolin-1-yl)-naphthalen-1-ol；2-(1,2,3,4-Tetrahydroisoquinolin-1-yl)-1-naphthol
• CAS: 897035-09-5
• 化学式: C₁₉H₁₇NO
• 分子量: 275.35
• InChiKey: HDAWKBGPOULHDO-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: isopropyl ether (108-20-3); ethyl acetate (141-78-6))
• 沸点：
  424.8±40.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 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：

  2-(1,2,3,4-四氢异喹啉-1-基)-1-萘酚 、 4-氯异硫氰酸苯酯 以 甲苯 为溶剂， 反应 24.0h， 以92%的产率得到N¹-[1-(1-hydroxy-2-naphthyl)-1,2,3,4-tetrahydroisoquinoline]-N²-p-chlorophenylthiourea
  参考文献：
  名称：

  萘[1,2- e ] [1,3]恶嗪[4,3- a ] [1,3]异喹啉和萘[2,1- e ] [1,3]恶嗪[4， 3- α ]异喹啉衍生物

  摘要：

  通过将1-（β-羟基萘基）-1,2,3,4-四氢异喹啉和1-（α-羟基萘基）-1,2,3,4-四氢异喹啉与甲醛，光气，对硝基苯甲醛或对-环化氯苯基异硫氰酸酯，8-取代的10,11-dihydro-8 H，15b H-萘[1,2- e ] [1,3]恶嗪基[4,3- a ]异喹啉（3和4）和10,11-二氢-8 H，15b H-萘[2,1- e ] [1,3]恶嗪基[4,3- a ]异喹啉（15和16）已准备好。通过NMR光谱对这些杂环的哌啶和1,3-恶嗪部分进行构象分析，并进行了理论研究，结果表明，这两个构象上灵活的六元环部分更喜欢使用扭曲的椅子构象异构体。

  DOI：

  10.1016/j.tet.2008.05.025
• 作为产物：
  描述：

  3,4-二氢异喹啉 、 萘酚 生成 2-(1,2,3,4-四氢异喹啉-1-基)-1-萘酚
  参考文献：
  名称：

  萘[1,2- e ] [1,3]恶嗪[4,3- a ] [1,3]异喹啉和萘[2,1- e ] [1,3]恶嗪[4， 3- α ]异喹啉衍生物

  摘要：

  通过将1-（β-羟基萘基）-1,2,3,4-四氢异喹啉和1-（α-羟基萘基）-1,2,3,4-四氢异喹啉与甲醛，光气，对硝基苯甲醛或对-环化氯苯基异硫氰酸酯，8-取代的10,11-dihydro-8 H，15b H-萘[1,2- e ] [1,3]恶嗪基[4,3- a ]异喹啉（3和4）和10,11-二氢-8 H，15b H-萘[2,1- e ] [1,3]恶嗪基[4,3- a ]异喹啉（15和16）已准备好。通过NMR光谱对这些杂环的哌啶和1,3-恶嗪部分进行构象分析，并进行了理论研究，结果表明，这两个构象上灵活的六元环部分更喜欢使用扭曲的椅子构象异构体。

  DOI：

  10.1016/j.tet.2008.05.025

文献信息

• CHIRAL LIGANDS, THEIR PREPARATION AND USES THEREOF IN ASYMMETRIC REACTIONS
  申请人：Li Chao-Jun

  公开号：US20090306390A1

  公开（公告）日：2009-12-10

  A novel class of chiral ligands represented by a structure of Formula (I): wherein R 1 , R 2 , R 3 , R 4 and R 5 are independently selected from the group consisting of hydrogen, halogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 1-10 alkoxy, C(O)R 6 , C(O)NHR 6 , Si(R 6 ) 3 , benzyl and aryl; X is selected from the group consisting of OH, OR 7 , O-Prot and P(R 7 ) 2 where Prot represents a protecting group; and R 6 and R 7 are selected from the group consisting of hydrogen, C 1-10 alkyl, C 2-10 alkenyl, C 2-10 alkynyl, C 1-10 alkoxy, phenyl, and aryl is disclosed herein.

  一种新型手性配体类别，其结构式表示为（I）式：其中R1、R2、R3、R4和R5独立地选自氢、卤素、C1-10烷基、C2-10烯基、C2-10炔基、C1-10烷氧基、C（O）R6、C（O）NHR6、Si（R6）3、苄基和芳基的群；X选自OH、OR7、O-Prot和P（R7）2的群，其中Prot代表保护基；R6和R7选自氢、C1-10烷基、C2-10烯基、C2-10炔基、C1-10烷氧基、苯基和芳基的群。
• Solvent-free direct aza-Friedel–Crafts reactions between 3,4-dihydroisoquinoline and 1- or 2-naphthols
  作者：Patricia D. MacLeod、Zhiping Li、Jianqing Feng、Chao-Jun Li

  DOI：10.1016/j.tetlet.2006.07.066

  日期：2006.9

  A self-catalytic aza-Friedel-Crafts method was employed to generate 1-naphtholyl tetrahydroisoquinoline products under neat conditions. In addition, a derivative was prepared in its enantiomerically pure form and has shown moderate activity for asymmetric catalysis in the asymmetric diethylzinc addition to aldehydes. (c) 2006 Elsevier Ltd. All rights reserved.
• Selective N -alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols
  作者：Judit Sas、István Szatmári、Ferenc Fülöp

  DOI：10.1016/j.tet.2015.03.011

  日期：2015.9

  The reactions of 1- or 2-naphthol, benzaldehyde or substituted benzaldehydes with tetrahydroisoquinoline, tetrahydrobenzo[d]azepine, tetrahydrobenzo[c]azepine or tetrahydrothieno[3,2-c]pyridine under solvent-free conditions, allowed a series of tertiary aminonaphthols to be prepared. The reactions were accelerated by the use of microwave irradiation, and the yields were also improved. As an exception, the aminoalkylation of 2-naphthol with 1,2,3,4-tetrahydroisoquinoline in the presence of benzaldehyde led to the parallel N-alkylation and redox alpha-arylation of the tetrahydroisoquinoline in a ratio of 4:1. The reaction of 1-naphthol with 2,3,4,5-tetrahydro-1H-benzo[c]azepine led to the formation of the N-alkylated compound as a single product, illustrating that the reaction route depends on the structures of the cyclic amine and the naphthol. (C) 2015 Elsevier Ltd. All rights reserved.
• WO2007/98608
  申请人：——

  公开号：——

  公开（公告）日：——
• Microwave-assisted, solvent-free synthesis of 1-(α- or β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction
  作者：István Szatmári、László Lázár、Ferenc Fülöp

  DOI：10.1016/j.tetlet.2006.03.169

  日期：2006.6

  As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereo-selective processes, resulting in the cis isomers as the main or the only products. (c) 2006 Elsevier Ltd. All rights reserved.