5,8-二氯异喹啉 | 73075-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 中文名称: 5,8-二氯异喹啉
• 中文别名: 5,8-二氯喹啉
• 英文名称: 5,8-dichloroisoquinoline
• 英文别名: 5,8-dichloro-isoquinoline；5,8-Dichlor-isochinolin
• CAS: 73075-59-9
• 化学式: C₉H₅Cl₂N
• mdl: MFCD07644632
• 分子量: 198.051
• InChiKey: MIYJUWWLNPMRCD-UHFFFAOYSA-N

物化性质

• 熔点：
  116-118 °C
• 沸点：
  321.4±22.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2933499090
• 危险性防范说明：
  P302+P352,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  5,8-二氯异喹啉 在 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 硫酸 、 水 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.0h， 生成 2-(5,8-dimethylisoquinolin-7-yl)aniline
  参考文献：
  名称：

  异喹啉碳环核的区域穷竭功能化：氧杂卟啉核和玫瑰树碱的合成

  摘要：

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。

  DOI：

  10.1055/s-0037-1609153
• 作为产物：
  描述：

  异喹啉 在 三氯异氰尿酸 、 硫酸 作用下， 以94%的产率得到5,8-二氯异喹啉
  参考文献：
  名称：

  异喹啉碳环核的区域穷竭功能化：氧杂卟啉核和玫瑰树碱的合成

  摘要：

  摘要 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。 已经开发了用于异喹啉碳环核心功能化的通用且通用的策略。这种区域穷举性方法采用亲电子卤化作为工具箱方法，并提供了装饰精美的中间体，可以将其进一步加工成与医学相关的构件或天然产物。

  DOI：

  10.1055/s-0037-1609153

文献信息

• BIPYRIDINE COMPOUND, TRANSITION METAL COMPLEX, AND METHOD FOR PRODUCTION OF CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20100184978A1

  公开（公告）日：2010-07-22

  A bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 each independently represent a C1-C10 alkyl group which may be substituted etc., and R 4 , R 5 , R 6 , R 7 and R 8 each independently represent a hydrogen atom etc., a transition metal complex obtained by contacting a bipyridine compound represented by the formula (1) with a compound of a transition metal belonging to Group 9, 10 or 11, and a method for production of a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of the transition metal complex.

  一种以式(1)表示的联吡啶化合物：其中R1、R2和R3各自独立地表示可以被取代的C1-C10烷基等，而R4、R5、R6、R7和R8各自独立地表示氢原子等，通过将式(1)表示的联吡啶化合物与属于9、10或11族过渡金属的化合物接触而获得的过渡金属配合物，以及一种制备共轭芳香化合物的方法，包括在过渡金属配合物的存在下，将一个或两个离去基团与芳环结合的芳香化合物（A）与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或结构不同于上述芳香化合物（A）且具有一个或两个离去基团与芳环结合的芳香化合物（B）反应。
• TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND USING THE TRANSITION METAL COMPLEX
  申请人：Asaumi Taku

  公开号：US20110046336A1

  公开（公告）日：2011-02-24

  A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R 1 , R 2 and R 3 represent a C1-C10 alkyl group which may be substituted, etc., and R 4 and R 5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.

  通过将式（1）所表示的联吡啶化合物与属于9、10或11族的过渡金属化合物接触而获得的过渡金属配合物，其中R1、R2和R3代表C1-C10烷基，可以被取代等，而R4和R5代表氢原子等。制备共轭芳香化合物的方法包括，在所述过渡金属配合物的存在下，将一个芳香化合物（A），其中一个或两个离去基团与芳香环相键合，与具有与上述芳香化合物（A）相同结构的芳香化合物（A）或在结构上不同于上述芳香化合物（A）并且具有一个或两个离去基团与芳香环相键合的芳香化合物（B）反应。
• TRANSITION METAL COMPLEX AND PROCESS FOR PRODUCING CONJUGATED AROMATIC COMPOUND WITH THE TRANSITION METAL COMPLEX
  申请人：Sumitomo Chemical Company, Limited

  公开号：EP2192124A1

  公开（公告）日：2010-06-02

  A transition metal complex obtained by contacting a bipyridine compound represented by the formula (1): wherein R1, R2 and R3 represent a C1-C10 alkyl group which may be substituted, etc., and R4 and R5 represent a hydrogen atom etc., with a compound of a transition metal belonging to Group 9, 10 or 11, and a process for producing a conjugated aromatic compound comprising reacting an aromatic compound (A) wherein one or two leaving groups are bonded to an aromatic ring with an aromatic compound (A) having the same structure as that of the above-mentioned aromatic compound (A) or an aromatic compound (B) being structurally different from the above-mentioned aromatic compound (A) and having one or two leaving groups bonded to an aromatic ring, in the presence of said transition metal complex.

  一种过渡金属配合物，通过与式 (1) 所代表的联吡啶化合物接触而获得： 其中 R1、R2 和 R3 代表可被取代的 C1-C10 烷基等，R4 和 R5 代表氢原子等、一种生产共轭芳香族化合物的工艺，包括在上述过渡金属配合物存在下，将一个或两个离去基团键合在芳香环上的芳香族化合物(A)与结构与上述芳香族化合物(A)相同的芳香族化合物(A)或结构不同于上述芳香族化合物(A)且一个或两个离去基团键合在芳香环上的芳香族化合物(B)反应。
• Inhibitors of phenylethanolamine N-methyltransferase and epinephrine biosynthesis. 1. Chloro-Substituted 1,2,3,4-tetrahydroisoquinolines
  作者：William E. Bondinell、Frederic W. Chapin、Gerald R. Girard、Carl Kaiser、Arnold J. Krog、Alex M. Pavloff、Mark S. Schwartz、Joanne S. Silvestri、Praful D. Vaidya

  DOI：10.1021/jm00179a007

  日期：1980.5

  In a search for inhibitors of epinephrine biosynthesis as potential therapeutic agents, a series of 13 ring-chlorinated 1,2,3,4-tetrahydroisoquinolines was prepared. These compounds were tested initially for their ability to inhibit rabbit adrenal phenylethanolamine N-methyltransferase (PNMT) in vitro. Enzyme-inhibitor dissociation constants, determined for the six most potent members of the series, indicated the following order of decreasing potency: 7,8-Cl2 greater than 6,7,8-Cl3 greater than 7-Cl approximately 5,6,7,8-Cl4 greater than 5,7,8-Cl3. These compounds were subsequently examined for PNMT-inhibiting activity in intact rats and mice. 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline (13, SK&F 64139) was the most potent member of the series both in vitro and in vivo and is currently undergoing clinical investigation.
• The Development of a New Manufacturing Route to the Novel Anticonvulsant, SB-406725A
  作者：Matthew D. Walker、Benjamin I. Andrews、Andrew J. Burton、Luke D. Humphreys、Gary Kelly、Mark B. Schilling、Peter W. Scott

  DOI：10.1021/op9002054

  日期：2010.1.15

  The development of an efficient manufacturing route to 3-acetyl-N-(5,8-dichloro-1,2,3,4-tetrahydro-7-isoquinolinyl)-4-(1-methylethyoxy)-benzamide hydrochloride SB-406725A (1) is described. Title synthesis begins with dichlorination of isoquinoline, followed by nitration using nitronium tetrafluoroborate in sulpholane. Nitroisoquinoline (12) was hydrogenated under pressure using Pt/C. The resultant tetrahydroisoquinoline (13) was selectively coupled with benzoate side chain (15) under base-promoted conditions using sodium hexamethyldisilazane to yield the parent molecule SB406725 (16). SB-406725 was then converted to the HCl salt SB-406725A (1). This process has been successfully demonstrated on a pilot-plant scale to prepare similar to 30 kg of SB-406725A (1).