2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物 | 6343-81-3

• 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: 2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物
• 中文别名: 2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮1,1-二氧化物；2-(2-羟基乙基)苯并[D]异噻唑-3(2H)-酮1,1-二氧化；2-(2-羟基乙基)苯并[D]异噻唑-3(2H)-酮 1,1-二氧化
• 英文名称: 2-(2-hydroxyethyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide
• 英文别名: 2-(2-hydroxyethyl)benzo[d]isothiazol-3(2H)-one 1,1-dioxide；2-(2-hydroxy-ethyl)-1,1-dioxo-1,2-dihydro-1λ⁶-benzo[d]isothiazol-3-one；2-(2-hydroxy-ethyl)-1,1-dioxo-1λ⁶-benz[d]isothiazol-3-one；2-(2-Hydroxy-aethyl)-1,1-dioxo-1λ⁶-benz[d]isothiazol-3-on；N-(2-hydroxyethyl)-1,2-benzisothiazol-3(2H)one-1,1-dioxide；N-(2-Hydroxy-ethyl)-o-sulfo-benzimid；2-(2-hydroxyethyl)-1,1-dioxo-1,2-benzothiazol-3-one
• CAS: 6343-81-3
• 化学式: C₉H₉NO₄S
• 分子量: 227.241
• InChiKey: CJWAPCSQEWUZAE-UHFFFAOYSA-N

物化性质

• 熔点：
  104-105 °C(Solv: methanol (67-56-1))
• 沸点：
  454.2±47.0 °C(Predicted)
• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 13.0h， 生成 2-(1,1,3-trioxo-2,3-dihydro-1,2-benzisothiazol-2-yl)ethyl-2,6-dimethyl-5-(ethoxycarbonyl)-4-methyl-1,4-dihydropyridinecarboxylate
  参考文献：
  名称：

  新的1,4-二氢吡啶的合成，血小板聚集抑制活性和体内抗血栓形成活性。

  摘要：

  合成了一系列与1,2-苯并噻唑-3结合的1,4-二氢吡啶（DHP），并评估了它们在富含人血小板的血浆（PRP）中抑制胶原蛋白诱导的血小板凝集和保护小鼠免于感染的能力。实验性血栓形成。结果表明该化合物是胶原诱导的血小板聚集的体外抑制剂。它们中的大多数在小鼠抗血栓测定中也有效降低了死亡率。2-（1,1,3-Trioxo-2,3-dihydro-1,2，benzithothiazol-2-yl）ethyl 2,6-二甲基-5-（乙氧基羰基）-4-甲基-1,4-二氢吡啶基羧基（4A）是最有前途的化合物。该化合物在麻醉的猫或麻醉的大鼠中分别以最高750或500微克/ kg的静脉注射剂量均未显示任何心血管作用。同样

  DOI：

  10.1021/jm00118a004
• 作为产物：
  描述：

  糖精 、 2-溴乙醇 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成 2-(2-羟基乙基)-1,2-苯并异噻唑-3(2H)-酮 1,1-二氧化物
  参考文献：
  名称：

  Sulfonamides as multifunctional agents for Alzheimer’s disease

  摘要：

  Sulfonamide linker-based inhibitors with extended linear structure were designed and synthesized with the aim of producing multifunctional agents against several processes involved in the pathology of Alzheimer's disease (AD). The potency of the compounds were assessed in the inhibition of Ab self-assembly (fibril and oligomer formation), in modulating cholinesterase (AChE, BuChE) activity, and scavenging free radicals. Several compounds exhibited promising Ab self-assembly and cholinesterase inhibition and in parallel, showed good free radical scavenging properties. The investigation of the scaffold described in this study resulted in the identification of three compounds (14, 19 and 26) as promising leads for the further design of multifunctional drug candidates for AD. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.12.006

文献信息

• Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Elham Zarenezhad、Narjes Kaviani

  DOI：10.1007/s13738-015-0633-9

  日期：2015.9

  Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-alkylation reaction with primary or secondary alcohols using TsCl/TEA/K2CO3 in bmim[Br] to afford the products in good-to-excellent yields. The influence of factors in this method including the type of ionic liquid, base and sulfonating agents was discussed. The current method showed an appropriate selectivity in reaction with primary alcohols in comparison with secondary alcohols. This protocol is mild, safe and easy to apply; moreover, it is quite compatible with eco-friendly and green chemistry protocols, since the exploitation of toxic and hazardous materials such as DMF and alkyl halides has been prevented.

  描述了一种在离子液体介质中使用醇对核苷碱基进行高效一锅法N-烷基化的协议，作为获取无环核苷的直接途径。在此协议中，嘌呤、嘧啶以及唑类衍生物与一级或二级醇在TsCl/TEA/K2CO3于bmim[Br]中进行N-烷基化反应，得到良好至极佳产率的产物。讨论了该方法中包括离子液类型、碱和磺化剂等因素的影响。当前方法在反应中对一级醇显示出适当的优先选择性，相较于二级醇。该协议温和、安全且易于应用；此外，由于避免了使用如DMF和烷基卤等有毒及危险材料，它与生态友好和绿色化学协议高度兼容。
• One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph 3 P/I 2 : simple route for carboacyclic nucleoside synthesis
  作者：Mohammad Navid Soltani Rad、Faezeh Soleimani

  DOI：10.1016/j.tet.2016.06.069

  日期：2016.8

  efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh3 and I2 is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph3P/I2 in the presence of Et3N-K2CO3 in anhydrous DMF to give the N-alkyl adducts (carboacyclic nucleosides)

  据报道，利用PPh 3和I 2的组合，通过醇进行一锅N-烷基化核碱基及其相关的N-杂环的简单有效的合成方案。在这个协议中嘌呤，嘧啶和吡咯衍生物经历与使用pH不同的伯醇的N-烷基化反应3 P / I 2的Et的存在3 N-K 2 CO 3在无水DMF，得到Ñ-烷基加合物（碳环核苷）的收率很高（高达90％）。讨论了该反应中一些参数的影响，包括溶剂类型，碱，试剂和温度。此外，该方案已证明对二醇中伯羟基相对于仲羟基具有良好的选择性。
• Triphenylphosphine-free approach for one-pot N-alkylation of purine, pyrimidine, and azole derivatives with alcohols using P2O5/KI: A facile and selective route to access carboacyclic nucleosides
  作者：Somayeh Behrouz、Mohammad Navid Soltani Rad、Samira Ahmadi

  DOI：10.1016/j.tet.2019.130499

  日期：2019.9

  A facile, selective, and mild synthetic approach for one-pot N-alkylation of nucleobases and other related N-heterocycles via alcohols, using a mixture of P2O5 and KI is described. The reaction of structurally diverse purines, pyrimidines, and/or azoles with primary alcohols with the use of P2O5/KI and basic mixture of Et3N/K2CO3 in refluxing DMF affords the corresponding N-alkyl derivatives (carboacyclic

  描述了一种使用P 2 O 5和KI的混合物通过醇通过一锅法对核碱基和其他相关N-杂环进行N-烷基化的简便，选择性和温和的合成方法。使用P 2 O 5 / KI和Et 3 N / K 2 CO 3的碱性混合物，使结构不同的嘌呤，嘧啶和/或唑与伯醇反应在回流中，DMF以良好至合理的产率得到相应的N-烷基衍生物（碳环核苷）。评估了包括溶剂，碱，温度和底物/试剂比率的不同参数对反应进程的影响。仲和叔醇不能与核碱基反应。当前方案的主要优点是形成水溶性副产物，其中提供了简单的后处理和纯化过程。
• A Simple, One-Pot and Phosphine-Free Procedure for Thiocyanation of Alcohols Using N-(p-toluenesulfonyl) Imidazole (TsIm)
  作者：Mohammad Navid Soltani Rad

  DOI：10.3184/174751916x14736925997854

  日期：2016.10

  efficient, one -pot, phosphine-free thiocyanation of alcohols has been achieved utilising potassium thiocyanate and N-(p-toluene sulfonyl) imidazole (TsIm) as a coupling agent in the presence of triethylamine in anhydrous DMF at 70 °C. This method converts primary alcohols into the corresponding thiocyanates, without isomerisation to isothiocyanates, in good to excellent yields. A total of 17 thiocyananates

  利用硫氰酸钾和 N-（对甲苯磺酰基）咪唑（TsIm）作为偶联剂，在三乙胺的存在下，在 70°C 的无水 DMF 中，实现了一种有效的、一锅法、不含膦的醇硫氰化反应。该方法将伯醇转化为相应的硫氰酸酯，无需异构化为异硫氰酸酯，收率良好或极好。共制备了 17 种硫氰酸盐，其中 5 种是新的。使用一当量的 KSCN，该方法在仲醇存在下的伯醇硫氰化反应中显示出良好的选择性。
• 1,4-Dihydropiridines and their use as antithrombotic drugs
  申请人：Alter, S.A.

  公开号：US04782069A1

  公开（公告）日：1988-11-01

  The present invention refers to new 1,4-dihydropyridines, to their obtention processes and to their use as antithrombotic drugs. Said new 1,4-dihdyropyridines have the following general formula (I) ##STR1## wherein R represents hydrogen or a saturated or unsaturated alkyl group, with a linear or branched chain of 1 to 8 carbon atoms, R.sup.1 represents an alkyl radical with a linear, branched or cyclic, saturated or unsaturated chain of 1 to 12 carbon atoms, which may be interrupted by an oxygen or by a 2-(N-salicylamido)ethyl group, n is a number equal to 1 or 2. These new 1,4-dihydropyridines are obtained by processes based on the Hantzch reaction or on modifications thereof.

  本发明涉及新型1,4-二氢吡啶，其制备过程以及作为抗血栓药物的用途。所述新型1,4-二氢吡啶具有以下通式（I）##STR1##其中R代表氢或具有1至8个碳原子的线性或支链饱和或不饱和烷基，R.sup.1代表具有1至12个碳原子的线性、支链或环状饱和或不饱和链的烷基基团，其可以被氧或2-(N-水杨酰胺)乙基基团所中断，n是等于1或2的数字。这些新型1,4-二氢吡啶是通过基于汉茨反应或其修饰的过程获得的。