3-(6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-丙-1-醇 | 148204-28-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 中文名称: 3-(6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-丙-1-醇
• 英文名称: 1-(3-hydroxypropyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• 英文别名: 3-(6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl)propan-1-ol
• CAS: 148204-28-8
• 化学式: C₁₄H₂₁NO₃
• 分子量: 251.326
• InChiKey: ATYQDEIGHYQNLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-丙-1-醇 在 氯化亚砜 作用下， 以 二氯甲烷 、 乙二醇二甲醚 、 水 为溶剂， 反应 3.0h， 以95%的产率得到(+/-)-crispine A
  参考文献：
  名称：

  SOCl 2对氨基醇的氯化/环脱水反应：一个古老的反应

  摘要：

  已经开发出一种简单的一锅法，通过使用SOCl 2对氨基醇进行有效氯化来制备环胺。该方法消除了通常用于这种类型的转化的经典的N-保护/ O-活化/环化/去保护序列的需要。还研究了该方法的反应途径和一般范围。

  DOI：

  10.1021/jo701877h
• 作为产物：
  描述：

  1-(3-hydroxypropyl)-6,7-dimethoxy-3,4-dihydroisoquinoline 在 sodium tetrahydroborate 作用下， 生成 3-(6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-丙-1-醇
  参考文献：
  名称：

  Total synthesis of crispine A enantiomers through a Burkholderia cepacia lipase-catalysed kinetic resolution

  摘要：

  Both enantiomers of the antitumour-active alkaloid crispine A (ee = 95%) were synthesised through the Burkholderia cepacia lipase-catalysed acylation of the primary hydroxy group of N-Boc-protected 1-(3-hydroxypropyl)-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline (+/-)-3 and the enantioselective hydrolysis of the corresponding O-decanoate (+/-)-4 [R = (CH2)(8)Me] with a remote, four-atom distant stereogenic centre. High enantioselectivities were observed for the (S)-selective O-acylation with vinyl decanoate in the presence of Et3N and Na2SO4 in t-BuOMe at 45 degrees C (E = 68), and for the (S)-selective hydrolysis with H2O in t-BuOMe at 45 degrees C (E = 52). The enzymatic resolutions, performed in two steps, afforded the key alcohol and ester enantiomers with high enantiomeric excesses (ee >= 94%). Ring-closure reactions of alcohol enantiomers (+)-3 and (-)-3 with thionyl chloride afforded the desired crispine A enantiomers (+)-1 and (-)-1 (ee >= 95%). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.06.026

文献信息

• Electrochemical Synthesis and Chemistry of Chiral 1-Cyanotetrahydroisoquinolines. An Approach to the Asymmetric Syntheses of the Alkaloid (−)-Crispine A and Its Natural (+)-Antipode
  作者：Fadila Louafi、Julie Moreau、Saurabh Shahane、Stéphane Golhen、Thierry Roisnel、Sourisak Sinbandhit、Jean-Pierre Hurvois

  DOI：10.1021/jo2017982

  日期：2011.12.2

  (90:10 dr) and (−)-11 (85:15 dr) were prepared from the alkylation–reduction sequence of a common α-amino nitrile (+)-4 derivative that has been conveniently prepared by anodic cyanation. Elaboration of the pyrrolidine ring of the title compound was cleanly achieved by two efficient ring closures methods involving (a) the displacement of a halogen atom and (b) the formation of a cyclic iminium cation to

  描述了四氢异喹啉（THIQ）生物碱香晶A的两种对映体的立体选择性会聚全合成。THIQ前体（-）- 6（90:10 dr）和（-）- 11（85:15 dr）是根据一种常见的α-氨基腈（+）- 4衍生物的烷基化还原序列制备的通过阳极氰化方便地制备。标题化合物的吡咯烷环的精制是通过两种有效的闭环方法完成的，其中包括（a）取代卤素原子和（b）形成环亚氨基阳离子，从而获得90％的（-）-crispine A和85％的收率。含有1当量（-）-DBTA的对映体富集（-）-crispine A（90:10 er）的结晶得到酒石酸盐（-）- 14（≥98：2 dr），产率为81％。简单地从酒石酸盐（-）- 14的X射线数据检查中可以得出（-）crispine A的绝对S构型。同样，在七个后处理步骤中以30％的总收率制备了天然（+）crispine A，并用（+）-DBTA相互结晶，得到了≥98：2 dr的对映体酒石酸盐（+）-
• Capture compounds, collections thereof and methods for analyzing the proteome and complex compositions
  申请人：Köster Hubert

  公开号：US20100298168A1

  公开（公告）日：2010-11-25

  Capture compounds and collections thereof and methods using the compounds for the analysis of biomolecules are provided. In particular, collections, compounds and methods are provided for analyzing complex protein mixtures, such as the proteome. The compounds are multifunctional reagents that provide for the separation and isolation of complex protein mixtures. Automated systems for performing the methods also are provided.

  提供了用于分析生物分子的捕获化合物及其集合和方法。特别是，提供了用于分析复杂蛋白质混合物（如蛋白质组）的集合、化合物和方法。这些化合物是多功能试剂，可用于分离和分离复杂的蛋白质混合物。还提供了执行这些方法的自动化系统。
• One-Pot Preparation of Cyclic Amines from Amino Alcohols
  作者：Xu, Feng、Simmons, Bryon

  DOI：10.15227/orgsyn.090.0251

  日期：——
• CN116178383
  申请人：——

  公开号：——

  公开（公告）日：——
• Total synthesis of crispine A enantiomers through a Burkholderia cepacia lipase-catalysed kinetic resolution
  作者：Enikő Forró、László Schönstein、Ferenc Fülöp

  DOI：10.1016/j.tetasy.2011.06.026

  日期：2011.6

  Both enantiomers of the antitumour-active alkaloid crispine A (ee = 95%) were synthesised through the Burkholderia cepacia lipase-catalysed acylation of the primary hydroxy group of N-Boc-protected 1-(3-hydroxypropyl)-6,7-bis(methyloxy)-1,2,3,4-tetrahydroisoquinoline (+/-)-3 and the enantioselective hydrolysis of the corresponding O-decanoate (+/-)-4 [R = (CH2)(8)Me] with a remote, four-atom distant stereogenic centre. High enantioselectivities were observed for the (S)-selective O-acylation with vinyl decanoate in the presence of Et3N and Na2SO4 in t-BuOMe at 45 degrees C (E = 68), and for the (S)-selective hydrolysis with H2O in t-BuOMe at 45 degrees C (E = 52). The enzymatic resolutions, performed in two steps, afforded the key alcohol and ester enantiomers with high enantiomeric excesses (ee >= 94%). Ring-closure reactions of alcohol enantiomers (+)-3 and (-)-3 with thionyl chloride afforded the desired crispine A enantiomers (+)-1 and (-)-1 (ee >= 95%). (C) 2011 Elsevier Ltd. All rights reserved.