1,2-苯并异噻唑-3-乙酸 | 29266-68-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 中文名称: 1,2-苯并异噻唑-3-乙酸
• 英文名称: 1,2-benzisothiazole-3-acetic acid
• 英文别名: benzo[d]isothiazol-3-yl-acetic acid；1,2-Benzoisothiazol-3-yl-essigsaeure；1,2-Benzoisothiazol-3-essigsaeure；1,2-Benzisothiazol-3-essigsaeure；3-Benzoisothiazolessigsaeure；2-(1,2-benzothiazol-3-yl)acetic acid
• CAS: 29266-68-0
• 化学式: C₉H₇NO₂S
• 分子量: 193.226
• InChiKey: HWLOCGLMEHUBAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090
• 危险性防范说明：
  P261,P264,P270,P271,P280,P301+P312,P302+P352,P304+P340,P305+P351+P338,P330,P332+P313,P337+P313,P362,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  1,2-苯并异噻唑-3-乙酸 在 硫酸 、 肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 benzo[d]isothiazol-3-yl-acetic acid acetylhydrazide
  参考文献：
  名称：

  Benzisoxazole and benzisothiazole analogs of auxin

  摘要：

  DOI：

  10.1016/s0031-9422(00)94694-6
• 作为产物：
  描述：

  1,2-Benzisothiazol-3-yl-acetic acid ethyl ester 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 1,2-苯并异噻唑-3-乙酸
  参考文献：
  名称：

  1,2-苯并异噻唑类。第三部分 3-取代衍生物

  摘要：

  （1,2-苯并噻唑-3-基）氰基乙酸乙酯是两种互变异构体的混合物，在二甲基亚砜中加热时会分解为（1,2-苯并异噻唑-3-基）乙腈（85％）。用乙醇乙醇钠处理（1,2-苯并噻唑-3-基）丙二酸二乙酯得到乙酸乙酯（1,2-苯并噻唑-3-基）乙酸乙酯，连续水解和脱羧得到3-甲基-1,2-苯并噻唑。3-甲基-1，2-苯并噻唑中的甲基具有抗氧化性。尝试用Vilsmeier-Haack将3-甲基-1,2-苯并噻唑与二甲基甲酰胺和磷酰氯进行甲酰化反应，得到N 2-（3-苯并[ b ]噻吩基）-N 1 N 1-二甲基甲am和N 2的混合物-（2-甲酰基-3-苯并[ b ]噻吩基）-N 1 N 1-二甲基甲am。相反，2-甲基苯并噻唑产生（苯并噻唑-2-基）丙二醛或相关的烯胺。

  DOI：

  10.1039/p19720003006

文献信息

• Complete ¹ H and ¹³ C NMR spectral assignment of benzo[<i>d</i> ]isothiazole derivatives and of an isoindole isoster
  作者：Matteo Incerti、Domenico Acquotti、Paola Vicini

  DOI：10.1002/mrc.2308

  日期：2008.12

  The complete 1H and 13C NMR assignments of the novel compound methyl 2‐amino‐3‐(benzo[d]isothiazol‐3‐yl)propanoate (1), of 3‐amino‐5‐methylbenzo[d]isothiazole (2) and N‐(t‐butyloxycarbonyl)‐2‐aminobenzo[d]isothiazol‐3(2H)‐one (3) and of the desulfurated isostere of 3, N‐(t‐butyloxycarbonyl)‐2‐aminoisoindolin‐1‐one (4), using 1D and 2D NMR techniques, including COSY, INADEQUATE, HSQC, and HMBC experiments

  新型化合物 2-氨基-3-(苯并[d]异噻唑-3-基)丙酸甲酯 (1)、3-氨基-5-甲基苯并[d]异噻唑 (2) 和N-(t-丁氧羰基)-2-氨基苯并[d]isothiazol-3(2H)-one (3) 和 3 的脱硫等排体，N-(t-丁氧羰基)-2-aminoisoindolin-1-one (4 )，使用 1D 和 2D NMR 技术，包括 COSY、INADEQUATE、HSQC 和 HMBC 实验。版权所有 © 2008 John Wiley & Sons, Ltd.
• Electrophilic substitution of 1,2-benzisothiazol-3-acetic acid.
  作者：HITOSHI UNO、MIKIO KUROKAWA

  DOI：10.1248/cpb.26.3888

  日期：——

  The bromination, the nitration, the chlorosulfonation, the formylation and the Mannich reaction of 1, 2-benzisothiaizol-3-acetic acid (1) were investigated and it was shown that the 3α-methylene group is also activated to the electrophilic substitutions as in 1, 2-benzisoxazol-3-acetic acid.

  研究了 1，2-苯并异噁唑-3-乙酸（1）的溴化、硝化、氯磺化、甲酰化和曼尼希反应，结果表明 3α-亚甲基也能像 1，2-苯并异噁唑-3-乙酸中的亲电取代那样被激活。
• 3-(1,2-benzisothiazol- and isoxazol-5-Y1)-2,4(1H,3H)-pyrimidinedione or thione and 3-(1,2-benzisothiazol- and isoxazol-5-y1)-4(3H)-pyrimidinone or thione herbicidal agents
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0908457B1

  公开（公告）日：2002-11-13
• Sato, Kazuo; Honma, Toyokuni; Sugai, Soji, Agricultural and Biological Chemistry, 1985, vol. 49, # 12, p. 3563 - 3568
  作者：Sato, Kazuo、Honma, Toyokuni、Sugai, Soji

  DOI：——

  日期：——
• Synthesis and pharmacological properties of benzisothiazole/benzimidazole derivatives with acidic groups
  作者：Paola Vicini、Matteo Incerti、Loredana Amoretti、Vigilio Ballabeni、Massimiliano Tognolini、Elisabetta Barocelli

  DOI：10.1016/s0014-827x(02)01219-3

  日期：2002.4

  The synthesis and the pharmacological evaluation of benzisothiazole and benzimidazole tetrazolyl- and carboxyl-derivatives 1-6 are described. Structural modification was aimed at investigating the influence of two isosteric substituents (tetrazolyl- and carboxyl-) on the title benzofused heterocycles. The antiphlogistic, antipyretic and analgesic activities have been investigated in in vivo experimental models. Additional investigations have been performed in vitro to study the antiplatelet and spasmolytic activity of the compounds synthetized. All the compounds produced peripheral analgesic effects, but were less effective in hot plate test. The tetrazole and the carboxylic benzisothiazole derivatives 2 and 3 proved to be the most effective drugs within the series, exhibiting maximal inhibition of writhes with a potency 3-fold higher than that of acetaminophen. Only compound 5 provided indication for a central analgesic activity since it was active in hot plate test although with a low potency. The findings obtained in these in vivo and in vitro studies indicate that these compounds do not share the same mechanism of action of acetaminophen. All of the compounds under study present lower acute toxicity than acetaminophen when orally administered in mice. (C) 2002 Published by Editions scientifiques et medicales Elsevier SAS.