6-甲氧基-苯并噻唑-4,7-二酮 | 50823-21-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 6-甲氧基-苯并噻唑-4,7-二酮
• 英文名称: 6-methoxy-benzothiazole-4,7-dione
• 英文别名: 6-Methoxybenzothiazole-4,7-dione；6-methoxy-1,3-benzothiazole-4,7-dione
• CAS: 50823-21-7
• 化学式: C₈H₅NO₃S
• 分子量: 195.199
• InChiKey: HABHDFMCOYESFF-UHFFFAOYSA-N

物化性质

• 沸点：
  388.4±42.0 °C(Predicted)
• 密度：
  1.50±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  84.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-甲氧基-苯并噻唑-4,7-二酮 在 硫酸 、 三氟乙酸 作用下， 以 溶剂黄146 为溶剂， 反应 3.75h， 生成 10-Methyl-[1,3]thiazolo[4,5-b]acridine-4,11-dione
  参考文献：
  名称：

  五环芳族生物碱，宽氨胺A，11-羟基阿斯卡德明和乙酸新愈伤组织的合成研究

  摘要：

  五环芳族生物碱，宽胺碱A（6）分三步合成，分别由6-甲氧基苯并噻唑-4,7-二酮（8）和2-氨基苯乙酮（9）组成。由5，8-喹啉二酮（13、14）或1，4-ac啶二酮（20）制备11-羟基天冬酰胺（4）。醋酸neocalliactine的结构，calliactine的衍生物，被确定为5通过全合成从6-甲氧基-5,8-二quinolinedione（28）和2-氨基-5-甲氧基苯乙酮（29）。

  DOI：

  10.1016/s0040-4020(97)10153-3
• 作为产物：
  描述：

  6-methoxy-7-aminobenzothiazole 生成 6-甲氧基-苯并噻唑-4,7-二酮
  参考文献：
  名称：

  Coenzyme Q. 166. Antimetabolites of coenzyme Q. 21. Synthesis of alkyl-4,7-dioxobenzothiazoles with prophylactic antimalarial activity

  摘要：

  DOI：

  10.1021/jm00269a026

文献信息

• Total Synthesis of Kuanoniamine A, 11-Hydroxyascididemin, and Neocalliactine Acetate
  作者：Yoshiyasu Kitahara、Shinsuke Nakahara、Takanobu Yonezawa、Masanori Nagatsu、Akinori Kubo

  DOI：10.3987/com-92-6321

  日期：——

  A pentacyclic aromatic alkaloid, kuanoniamine A (5) was synthesized from 6-methoxybenzothiazole-4,7-dione (7) and 2-aminoacetophenone (8). Similarly, 11-hydroxyascididemin (4) was prepared from 6-bromo-4-chloro-5,8-dimethoxyquinoline (12). The structure of neocalliactine acetate, a derivative of calliactine, was determined at 19 by total synthesis from 6-methoxy-5,8-quinolinedione (23) and 2-amino-5-methoxyacetophenone (24).
• Synthesis and antifungal activity of 6-arylthio-/6-Arylamino-4,7-dioxobenzothiazoles
  作者：Chung-Kyu Ryu、Ko Un Choi、Ju-Yeon Shim、Hea-Jung You、Ik Hwa Choi、Mi Jin Chae

  DOI：10.1016/s0968-0896(03)00390-0

  日期：2003.9

  6-Arylthio-/6-arylamino-4,7-dioxobenzothiazoles were synthesized and tested for in vitro antifungal activity against Candida species and Aspergillus niger. 6-Arylamino-4,7-dioxobenzothiazoles 5 and 6 showed, in general, more potent antifungal activity than 6-arylthio-4,7-dioxobenzothiazoles 3 and 4. The 6-arylamino-substituted compounds 5 and 6 exhibited the greatest activity. In contrast, 6-arylthio-, 2-/5-methyl- or 5-methoxy-moieties of compounds 3-4 did not improve their antifungal activity significantly. The results of this study suggest that 6-arylamino-4,7-dioxobenzothiazoles would be potent antifungal agents. (C) 2003 Elsevier Ltd. All rights reserved.
• Coenzyme Q. 166. Antimetabolites of coenzyme Q. 21. Synthesis of alkyl-4,7-dioxobenzothiazoles with prophylactic antimalarial activity
  作者：Martin D. Friedman、Philip L. Stotter、Thomas H. Porter、Karl Folkers

  DOI：10.1021/jm00269a026

  日期：1973.11
• Synthetic studies on pentacyclic aromatic alkaloids, kuanoniamine A, 11-hydroxyascididemin, and neocalliactine acetate
  作者：Yoshiyasu Kitahara、Shinsuke Nakahara、Takanobu Yonezawa、Masanori Nagatsu、Yoshikazu Shibano、Akinori Kubo

  DOI：10.1016/s0040-4020(97)10153-3

  日期：1997.12

  A pentacyclic aromatic alkaloid, kuanoniamine A (6) was synthesized in three steps from 6-methoxybenzothiazole-4,7-dione (8) and 2-aminoacetophenone (9). 11-Hydroxyascididemin (4) was prepared from 5,8-quinolinedione (13, 14) or 1,4-acridinedione (20). The structure of neocalliactine acetate, a derivative of calliactine, was determined to be 5 by total synthesis from 6-methoxy-5,8-quinolinedione (28)

  五环芳族生物碱，宽胺碱A（6）分三步合成，分别由6-甲氧基苯并噻唑-4,7-二酮（8）和2-氨基苯乙酮（9）组成。由5，8-喹啉二酮（13、14）或1，4-ac啶二酮（20）制备11-羟基天冬酰胺（4）。醋酸neocalliactine的结构，calliactine的衍生物，被确定为5通过全合成从6-甲氧基-5,8-二quinolinedione（28）和2-氨基-5-甲氧基苯乙酮（29）。
• Synthesis and antifungal activities of 5/6-arylamino-4,7-dioxobenzothiazoles
  作者：Chung-Kyu Ryu、Hye-Young Kang、Yu-Jin Yi、Keun-Hwa Shin、Byung-Hoon Lee

  DOI：10.1016/s0960-894x(00)00301-2

  日期：2000.7

  5/6-Arylamino-4,7 -dioxobenzothiazoles were synthesized and tested for in vitro antifungal activities against pathogenic fungi. Most of the tested 4,7-dioxobenzothiazoles exhibited potent antifungal activities against Candida species and Aspergillus niger (C) 2000 Elsevier Science Ltd. All rights reserved.