thieno<2,3-d><1,2,3>thiadiazole-6-carboxylic acid methyl ester | 192878-28-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: thieno<2,3-d><1,2,3>thiadiazole-6-carboxylic acid methyl ester
• 英文别名: thieno<2,3-d>-1,2,3-thiadiazole-6-carboxylic acid methyl ester；Methyl thieno[2,3-d][1,2,3]thiadiazole-6-carboxylate；methyl thieno[2,3-d]-1,2,3-thiadiazole-6-carboxylate；thieno[2,3-d]1,2,3-thiadiazole-6-carboxylic acid methyl ester；methyl thieno[2,3-d]thiadiazole-6-carboxylate
• CAS: 192878-28-7
• 化学式: C₆H₄N₂O₂S₂
• 分子量: 200.242
• InChiKey: IXPHIUMCXCUSNK-UHFFFAOYSA-N

物化性质

• 沸点：
  307.6±45.0 °C(Predicted)
• 密度：
  1.578±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thieno<2,3-d><1,2,3>thiadiazole-6-carboxylic acid methyl ester 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以98%的产率得到thieno[2,3-d][1,2,3]thiadiazole-6-carboxylic acid
  参考文献：
  名称：

  A new type of plant activator: synthesis of thieno[2,3-d ][1,2,3]thiadiazole-6-carboxylic acid derivatives via Hurd–Mori cyclization

  摘要：

  我们提出了一种以廉价且容易获得的亚甲基丁二酸和硫代乙酸为起始原料的标题化合物的简短而有效的合成方法。优化的序列允许通过几个步骤大规模制备这种新型植物活化剂。邻位锂化用于将取代基引入5-位。建议对 Hurd–Mori 反应的反应机制进行修改来解释意外的芳构化。

  DOI：

  10.1039/a708375k
• 作为产物：
  描述：

  衣康酸 在 劳森试剂 、 sodium hydroxide 、 氯化亚砜 、 水 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醚 、 乙醇 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 70.5h， 生成 thieno<2,3-d><1,2,3>thiadiazole-6-carboxylic acid methyl ester
  参考文献：
  名称：

  A new type of plant activator: synthesis of thieno[2,3-d ][1,2,3]thiadiazole-6-carboxylic acid derivatives via Hurd–Mori cyclization

  摘要：

  我们提出了一种以廉价且容易获得的亚甲基丁二酸和硫代乙酸为起始原料的标题化合物的简短而有效的合成方法。优化的序列允许通过几个步骤大规模制备这种新型植物活化剂。邻位锂化用于将取代基引入5-位。建议对 Hurd–Mori 反应的反应机制进行修改来解释意外的芳构化。

  DOI：

  10.1039/a708375k

文献信息

• An improved synthetic approach to thieno[2,3-<i>d</i>]-1,2,3-thiadiazolecarboxylates<i>via</i>diazotization of aminothiophene derivatives
  作者：Peter Stanetty、Erwin Görner、Marko D. Mihovilovic

  DOI：10.1002/jhet.5570360330

  日期：1999.5

  The common synthetic method for the synthesis of fused 1,2,3-thiadiazoles via diazotization is not generally applicable to aminothiophenes. A substantially improved experimental protocol for the preparation of the title compounds as a potential inducer of systemic acquired resistance in plants is reported based on a novel cyclization mechanism via a Huisgen-White type rearrangement.

  通过重氮化合成稠合的1,2,3-噻二唑的常用合成方法通常不适用于氨基噻吩。基于经由Huisgen-White类型重排的新型环化机制，报道了用于制备标题化合物作为植物中系统获得性抗性的潜在诱导剂的实质上改进的实验方案。
• Microbicides
  申请人：Novartis Finance Corporation

  公开号：US05814629A1

  公开（公告）日：1998-09-29

  The invention relates to novel microbicidal and plant-immunising compounds of formula I ##STR1## wherein: X is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, SR.sub.8, N(R.sub.9)R.sub.10, CH.sub.2 OH, CHO or COOR.sub.8 ; R.sub.8 to R.sub.10 are hydrogen, C.sub.1 -C.sub.4 alkyl, benzyl, C.sub.1 -C.sub.4 acyl or benzoyl; Z is hydrogen, halogen, or a methyl group that is unsubstituted or to which from 1 to 3 unsubstituted or substituted hetero atoms O, S and/or N are bonded; in free form or in the form of salts. They can be used in crop protection for controlling and preventing disease infestation.

  本发明涉及一种新型杀菌和植物免疫化合物，其化学式为I ##STR1## 其中：X是氢、卤素、C.sub.1-C.sub.4烷基、SR.sub.8、N（R.sub.9）R.sub.10、CH.sub.2OH、CHO或COOR.sub.8；R.sub.8到R.sub.10是氢、C.sub.1-C.sub.4烷基、苯甲基、C.sub.1-C.sub.4酰基或苯甲酰基；Z是氢、卤素或一个未取代或与1到3个未取代或取代的杂原子O、S和/或N结合的甲基基团；以自由形式或盐的形式存在。它们可用于作物保护，控制和预防疾病侵染。
• 噻吩并噻二唑衍生物及其作为植物抗病激活 剂的应用
  申请人：华东理工大学

  公开号：CN103509039B

  公开（公告）日：2017-07-28

  发明涉及式I所示的噻吩并噻二唑系列衍生物及其作为植物抗病激活剂的应用。
• Novel plant activators with thieno[2,3-d]-1,2,3-thiadiazole-6-carboxylate scaffold: Synthesis and bioactivity
  作者：Qing-Shan Du、Yan-Xia Shi、Peng-Fei Li、Zhen-Jiang Zhao、Wei-Ping Zhu、Xu-Hong Qian、Bao-Ju Li、Yu-Fang Xu

  DOI：10.1016/j.cclet.2013.07.003

  日期：2013.11

  The 1,2,3-thiadiazole-carboxylate moiety was reported to be an important pharmacophore of plant activators. In this study, a series of novel plant activators based on thieno[2,3-d]-1,2,3-thiadiazole-6-carboxylate were designed and synthesized and their biological activity as plant activators was studied. The structures of the novel compounds were identified by H-1 NMR, F-19 NMR and HRMS. The in vivo bioassay showed that these novel compounds had good efficacy against seven plant diseases. Especially, compounds 1a and 1c were more potent than the commercialized plant activator BTH. Almost no fungicidal activity was observed for the active compounds in the in vitro assay, which matched the requirements as plant activators. (C) 2013 Bao-Ju Li and Yu-Fang Xu. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.
• A new type of plant activator: thieno[2,3-<i>d</i>][1,2,3]thiadiazole-6-carboxylic acid derivatives
  作者：Peter Stanetty、Manfred Kremslehner、Marion Jaksits

  DOI：10.1002/(sici)1096-9063(1998110)54:3<316::aid-ps838>3.0.co;2-c

  日期：1998.11

  A short and efficient synthesis of a series of the title compounds is presented starting with methylenebutanedioic acid and thioacetic acid. Using the: Hurd-Mori reaction in the key step, the optimised reaction sequence allows the large-scale preparation of this new type of plant activator in a few steps with a high overall yield. Additional functionalisation of the 5-position via directed ortho-lithiation methodology is also described. (C) 1998 Society of Chemical Industry.