1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrogen chloride | 52210-49-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢异喹啉
• 英文名称: 1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrogen chloride
• 英文别名: 1-(Chloromethyl)-3,4-dihydro-6,7-dimethoxyisoquinoline hydrochloride；1-chloromethyl-6,7-dimethoxy-3,4-dihyroisoquinoline hydrochloride；1-chloromethyl-6,7-dimethoxy-3,4-dihydro-isoquinoline; hydrochloride；1-Chlormethyl-6,7-dimethoxy-3,4-dihydro-isochinolin; Hydrochlorid；1-chloromethyl-6,7-dimethoxy-3,4-dihydro-isoquinoline hydrochloride；1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride；1-(Chloromethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline hydrochloride；1-(chloromethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;hydrochloride
• CAS: 52210-49-8
• 化学式: C₁₂H₁₄ClNO₂*ClH
• 分子量: 276.163
• InChiKey: WXLYUFVXBYMPNV-UHFFFAOYSA-N

物化性质

• 熔点：
  45 °C

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  30.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrogen chloride 在 sodium hydroxide 、 sodium tetrahydroborate 、 potassium carbonate 作用下， 以 甲醇 、 乙醇 为溶剂， 5.0 ℃ 、151.99 kPa 条件下， 反应 30.0h， 生成 (6,7-二甲氧基-1,2,3,4-四氢-异喹啉-1-基)-甲醇
  参考文献：
  名称：

  Reduction and Carboxylation of 1-Chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinium Salts. An Easy Entry to 1-Hydroxymethyl-1,2,3,4-tetrahydroisoquinoline Alkaloids

  摘要：

  At 25 degrees C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0 degrees C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (+/-)-Calycotomine and its N-Me derivative were obtained in high yields.

  DOI：

  10.3987/com-95-7285
• 作为产物：
  描述：

  1-(chloromethyl)-6,7-dimethoxy-3,4-dihydroisoquinoline;dichlorophosphinic acid 在 盐酸 作用下， 以 甲醇 、 乙醚 为溶剂， 以86%的产率得到1-chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinoline hydrogen chloride
  参考文献：
  名称：

  Reduction and Carboxylation of 1-Chloromethyl-6,7-dimethoxy-3,4-dihydroisoquinolinium Salts. An Easy Entry to 1-Hydroxymethyl-1,2,3,4-tetrahydroisoquinoline Alkaloids

  摘要：

  At 25 degrees C, the NaBH4/MeOH reduction of the title isoquinolinium salts gave the aziridine exclusively. At a low temperature (0 degrees C) in the presence of CO2/K2CO3, the 2-oxazolidinone was obtained in almost quantitative yield. Controlled hydrolysis of the borane complex derived from the isoquinolinium salts also gave the cyclic carbamate. (+/-)-Calycotomine and its N-Me derivative were obtained in high yields.

  DOI：

  10.3987/com-95-7285

文献信息

• Tetrahydro isoquinoline derivatives, preparation methods and medicinal uses thereof
  申请人：Xu Yungen

  公开号：US20090275607A1

  公开（公告）日：2009-11-05

  A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R 1 , R 2 , R 3 , R 4 of general formula (I) are defined as the description.

  一种四氢异喹啉衍生物（I），其制备方法，药物组合物及其药用，特别是其作为疼痛缓解中κ-阿片受体兴奋剂的用途，属于药物化学。 通用式（I）中的取代基R1，R2，R3，R4被定义为描述中所述。
• Discovery, stereospecific characterization and peripheral modification of 1-(pyrrolidin-1-ylmethyl)-2-[(6-chloro-3-oxo-indan)-formyl]-1,2,3,4-tetrahydroisoquinolines as novel selective κ opioid receptor agonists
  作者：Zong-Jie Gan、Yu-Hua Wang、Yun-Gen Xu、Ting Guo、Jun Wang、Qiao Song、Xue-Jun Xu、Shi-Yuan Hu、Yu-Jun Wang、De-Chuan Wang、De-Zhu Sun、Di Zhang、Tao Xi、Hao-Dong Li、Hai-Bo Zhang、Tai-Jun Hang、Hong-Guo Lu、Jing-Gen Liu

  DOI：10.1039/c5ob00350d

  日期：——

  11aproduces potent peripheral antinociception.

  11a产生强效的外周止痛作用。

• Pharmaceutically effective novel 3,4-dihydro-1,2- and 1,3-thiozolo [4,3a] i
  申请人：Chinoin Pharmaceutical and Chemical Works Ltd.

  公开号：US03979397A1

  公开（公告）日：1976-09-07

  The invention relates to new thiazoloisoquinolines of the general formula (I), or salts thereof, ##SPC1## Wherein A stands for a group of the formula ##EQU1## R.sup.1 stands for hydrogen, hydroxy, alkoxy or aralkoxy, R.sup.2 stands for hydrogen, hydroxy, alkoxy or aralkoxy, R.sup.3 stands for hydrogen, alkyl, aryl, nitro, carboxy or a carboxy derivative, and Y stands for oxygen, sulfur, or a group of the formula =N--R.sup.4, wherein R.sup.4 stands for hydrogen, alkyl, aryl, acyl, alkylsulfonyl or arylsulfonyl. These new compounds can be used in practice as heart medicines or respiratory analeptics. The new compounds according to the invention can be prepared as follows: an isoquinoline of the general formula (II) or a salt thereof ##SPC2## Wherein R.sup.5 stands for hydrogen, hydroxy, alkoxy or aralkoxy, R.sup.6 stands for hydrogen, hydroxy, alkoxy or aralkoxy, R.sup.7 stands for hydrogen, alkyl, aryl, carboxy or a carboxy derivative, and X stands for hydrogen, halogen or mercapto, Is reacted with a reactive carbonic acid derivative, provided that at least one of the reactants contains a sulfur atom, and/or an isoquinoline of the general formula (III) ##SPC3## wherein R.sup.5, R.sup.6 and R.sup.7 each have the same meanings as defined above, and Y' stands for oxygen, sulfur or a group of the formula =N--R.sup. 8, wherein R.sup.8 represents hydrogen, alkyl, aryl, acyl, arylsulfonyl or alkylsulfonyl, is oxidized, and/or substituents A', R.sup.5, R.sup.6 and R.sup.7 of the obtained thiazoloisoquinoline of the general formula (IA) ##SPC4## wherein A' stands for a group of the formula ##EQU2## and R.sup.5, R.sup.6, R.sup.7 and Y' each have the same meanings as defined above, are converted into those required in the end-products.

  本发明涉及一般式(I)的新噻唑异喹啉或其盐，其中A代表式的基团；R1代表氢、羟基、烷氧基或芳基氧基；R2代表氢、羟基、烷氧基或芳基氧基；R3代表氢、烷基、芳基、硝基、羧基或羧基衍生物；Y代表氧、硫或式的基团，其中R4代表氢、烷基、芳基、酰基、烷基磺酰基或芳基磺酰基。这些新化合物可实际用作心脏药物或呼吸兴奋剂。根据本发明，可以如下制备新化合物：一般式(II)的异喹啉或其盐或一般式(III)的异喹啉，其中R5、R6和R7具有上述定义的相同含义，Y'代表氧、硫或式的基团，其中R8代表氢、烷基、芳基、酰基、芳基磺酰基或烷基磺酰基，进行反应，提供至少一个反应物含有硫原子的反应性碳酸衍生物，和/或氧化一般式(III)，并/或将所得到的一般式(IA)的噻唑异喹啉的取代基A'、R5、R6和R7转化为所需的最终产物。
• TETRAHYDRO ISOQUINOLINE DERIVATIVES, PREPARATION METHODS AND MEDICINAL USES THEREOF
  申请人：China Pharmaceutical University

  公开号：EP2045243A1

  公开（公告）日：2009-04-08

  A kind of tetrahydro isoquinoline derivatives (I), their preparation methods, medicine compositions and medicinal uses thereof, especially their uses as κ-opioid receptor excitant in pain relieving, which belongs to the medicine chemistry. The substituents R1, R2, R3, R4 of general formula (I) are defined as the description.

  一种四氢异喹啉衍生物(I)及其制备方法、药物组合物和药用用途，特别是作为κ-阿片受体兴奋剂在止痛方面的用途，属于药物化学领域。 通式（I）中的取代基 R1、R2、R3、R4 的定义见说明。
• The intermolecular benzyne cycloaddition (IBC) approach to7-substituted aporphinoids. Mechanistic considerations
  作者：N. Atanes、L. Castedo、A. Cobas、E. Guitián、C. Saá、J.M. Saá

  DOI：10.1016/s0040-4020(01)85806-3

  日期：——