6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-8-ol | 156634-90-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-8-ol
• 英文别名: 6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-8-ol
• CAS: 156634-90-1
• 化学式: C₁₁H₁₃NO₃
• 分子量: 207.229
• InChiKey: CZXBVWOWWSHCJF-UHFFFAOYSA-N

物化性质

• 沸点：
  342.5±42.0 °C(Predicted)
• 密度：
  1.332±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-8-ol 在 正丁基锂 、 碘 作用下， 生成 9-Iodo-6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-8-ol
  参考文献：
  名称：

  Three complementary methods offering access to 5-substituted 1,2,3,4-tetrahydroisoquinolines

  摘要：

  The scope and limitations of three independent though related routes leading to 5-substituted tetrahydroisoquinolines are explored : the Pidet-Spengler type cyclization of ortho-substituted 2-phenylethylamines, the Pomeranz-Fritsch type cyclization of meta-substituted benzylamines and the electrophilic trapping of 5-lithiated 4-lithiooxytetrahydroquinolines. The introduction of the substituent relies in all three cases on a neighboring group assisted site selective metalation step. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00541-9
• 作为产物：
  描述：

  5-(benzo[d][1,3]dioxol-5-yl)-3-methyloxazolidine 在 盐酸 作用下， 以 水 为溶剂， 生成 6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-8-ol
  参考文献：
  名称：

  一锅合成4-氢异喹啉-4-醇的新型酸催化的5-芳基恶唑烷的重排

  摘要：

  带有给电子取代基的苯甲醛与肌氨酸和甲醛衍生的不稳定的偶氮甲嘧啶内酯平稳反应，形成5-芳基恶唑烷作为中间体，高产率地重排为2-甲基-1,2,3,4-四氢异喹啉-4-醇。通过用盐酸简单加热。一锅合成的四氢异喹啉可以认为是甲亚胺叶立德与芳族醛的正式[3 + 3]环加成反应。

  DOI：

  10.1016/j.tetlet.2013.02.087

文献信息

• 5-Aryloxazolidines as Reagents for Double Alkylation of Arenes: A Novel Synthesis of 4-Aryltetrahydroisoquinolines
  作者：Evgeny M. Buev、Anastasia A. Smorodina、Vladimir S. Moshkin、Vyacheslav Y. Sosnovskikh

  DOI：10.1021/acs.joc.1c01881

  日期：2021.11.5

  double alkylation sequence to give alkaloid-like 4-aryltetrahydroisoquinolines in 12–94% yields. Three approaches for the controlled insertion of substituents into the target molecules and application of oxazolidine derivatives such as 1-arylethanol-2-amines or 4-hydroxytetrahydroisoquinolines in the alkylation of arenes are also described. An unprecedented two-step easily scalable synthesis of the

  5-芳基恶唑烷在路易斯酸或布朗斯台德酸条件下通过 Friedel-Crafts/Pictet-Spengler 双烷基化序列与芳烃反应，以 12-94% 的产率得到生物碱样 4-芳基四氢异喹啉。还描述了将取代基受控插入目标分子的三种方法以及 1-芳基乙醇-2-胺或 4-羟基四氢异喹啉等恶唑烷衍生物在芳烃烷基化中的应用。应用恶唑烷方法实现了前所未有的两步可轻松扩展的从芳香醛合成 4-芳基四氢异喹啉核心。
• T-TYPE CALCIUM CHANNEL INHIBITOR
  申请人：NISSAN CHEMICAL INDUSTRIES, LTD.

  公开号：US20160237071A1

  公开（公告）日：2016-08-18

  A novel compound that has an excellent T-type calcium channel inhibitory activity and is specifically useful for prevention or treatment of pain, chronic kidney disease and atrial fibrillation. The novel triazinone compound of Formula (I): where each substituent in the formula is defined in detail in the description, and R 1 could be a hydrogen atom, or a C 1-6 alkyl group, etc., E could be a 7 to 14-membered non-aromatic fused heterocyclic group, L 3 could be a C 1-6 alkylene group, etc., D could be a C 6-14 aryl group or a 5 to 10-membered heteroaryl group each of which is optionally substituted, etc., a tautomer of the compound, or a pharmaceutically acceptable salt thereof, or a solvate thereof.

  一种新型化合物，具有出色的T型钙通道抑制活性，特别适用于预防或治疗疼痛、慢性肾脏疾病和心房颤动。该新型三嗪酮化合物的化学式为（I），其中公式中的每个取代基在描述中都有详细定义，R1可以是氢原子或C1-6烷基等，E可以是7-14个成员的非芳香融合杂环基，L3可以是C1-6亚烷基等，D可以是C6-14芳基或5-10个成员的杂环芳基，每个基团都可以有选择性地取代等，该化合物的互变异构体或药学上可接受的盐或溶剂化物。
• 76. Attempts to prepare derivatives of 1 : 2-dihydroisoquinoline. New interpretation of J. S. Buck's experiments on the synthesis of so-called 1 : 2-dihydropapaverine
  作者：P. C. Young、Robert Robinson

  DOI：10.1039/jr9330000275

  日期：——
• The spontaneous cyclodimerization of 2,3-dihydroisoquinolines after base promoted elimination of methanol from 4-methoxy-1,2,3,4-tetrahydroisoquinolines
  作者：Gyula Simig、Manfred Schlosser

  DOI：10.1016/s0040-4039(00)76833-x

  日期：1994.5

  The reaction of 4-metboxy-1,2,3,4-tetrahydroisoquinolines 1 with lithium diisopropyl-amide affords dimerization products 4. The intermediacy of orthoquinodimethanes 2 and diradicals 3 is assumed.
• A one-pot synthesis of tetrahydroisoquinolin-4-ols via a novel acid-catalyzed rearrangement of 5-aryloxazolidines
  作者：Vladimir S. Moshkin、Vyacheslav Ya. Sosnovskikh

  DOI：10.1016/j.tetlet.2013.02.087

  日期：2013.5

  nonstabilized azomethine ylide derived from sarcosine and formaldehyde to form 5-aryloxazolidines as intermediates, which undergo rearrangement into 2-methyl-1,2,3,4-tetrahydroisoquinolin-4-ols in high yields by simple heating with hydrochloric acid. This one-pot synthesis of tetrahydroisoquinolines can be considered as a formal [3+3] cycloaddition of the azomethine ylide to the aromatic aldehyde.

  带有给电子取代基的苯甲醛与肌氨酸和甲醛衍生的不稳定的偶氮甲嘧啶内酯平稳反应，形成5-芳基恶唑烷作为中间体，高产率地重排为2-甲基-1,2,3,4-四氢异喹啉-4-醇。通过用盐酸简单加热。一锅合成的四氢异喹啉可以认为是甲亚胺叶立德与芳族醛的正式[3 + 3]环加成反应。