methyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-ylidene]ethanoate | 1350766-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-ylidene]ethanoate
• 英文别名: methyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-yliden]ethanoate
• CAS: 1350766-31-2
• 化学式: C₁₃H₁₀ClNO₃S₂
• 分子量: 327.812
• InChiKey: IWTGDNZSGVYOOO-UHFFFAOYSA-N

物化性质

• 沸点：
  448.5±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.76
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-ylidene]ethanoate 、 丁炔二酸二乙酯 、 噻莫西酸 以 乙醇 为溶剂， 反应 3.33h， 以87%的产率得到
  参考文献：
  名称：

  非对映选择性合成功能化的吡咯并吡咯烷连接的若丹宁

  摘要：

  摘要官能化spiropyrrolizidine联绕丹宁甲非对映实际的路线已经通过与甲亚胺叶立德，原位制备从alkylidenerhodanines的1,3-偶极环加成反应已经开发升在回流-脯氨酸和炔酯，在EtOH。该协议可以以中等到良好的产率快速访问一系列结构多样的目标分子。通过X射线晶体学确定典型产物的结构。 图形摘要

  DOI：

  10.1007/s00706-019-02485-5
• 作为产物：
  描述：

  对氯苄胺 在 β-环糊精 作用下， 以 水 为溶剂， 反应 0.29h， 生成 methyl 2-[3-((4-chlorophenyl)methyl)-4-oxo-2-thioxo-1,3-thiazolan-5-ylidene]ethanoate
  参考文献：
  名称：

  Application of the β-cyclodextrin supramolecules as a green accelerator hosts in one-step preparation of highly functionalised rhodanine scaffolds

  摘要：

  beta-Cyclodextrin (beta-CD) supramolecule was found to be a convenient, green and economical tool in one-pot synthesis of rhodanine scaffolds as a highly efficient mediating agent in aqueous media in which the reaction accelerated to complete in 15min and room temperature. In this work, amines reacted with equimolar ratio of CS2 (not excess ratio of CS2) and then with activated acetylenes in the presence of beta-CD in aqueous media.

  DOI：

  10.1080/10610278.2014.890200

文献信息

• EtOAc-dispersed magnetic nanoparticles (DMNPs) of γ-Fe2O3 in the single-pot domino preparation of 5-oxo-2-thioxo-3-thiophenecarboxylate derivatives
  作者：Sadegh Rostamnia

  DOI：10.1016/j.crci.2013.03.002

  日期：2013.11

  Résumé EtOAc-dispersed magnetic nanoparticles (DMNPs) of γ-Fe2O3 represent a straightforward and green catalyst for the rapid three-component synthesis of 5-oxo-2-thioxo-3-thiophenecarboxylate derivatives as rhodanine skeletons via a single-pot domino process. The rhodanines were prepared over magnetic nanoparticles of γ-Fe2O3 without any salt or additives. Dispersed nano-γ-Fe2O3 have many advantages, such as stability in air, reusability, reactions with high efficiency, simple separation with magnetic external field from mixture reactions, chemical stability, and also low toxicity.

  摘要 EtOAc-分散的γ-Fe2O3磁性纳米粒子（DMNPs）是一种直接、绿色的催化剂，可通过单锅多米诺过程，以罗丹宁为骨架，快速合成 5-氧代-2-硫酮-3-噻吩羧酸酯衍生物的三组分化合物。这些罗丹宁是在γ- 的磁性纳米粒子上制备的，不含任何盐或添加剂。分散纳米γ- 具有许多优点，如在空气中稳定、可重复使用、反应效率高、利用磁场从混合物反应中分离简单、化学性质稳定以及毒性低等。
• A Rapid, Catalyst-Free, Three-Component Synthesis of Rhodanines in Water Using Ultrasound
  作者：Sadegh Rostamnia、Kamran Lamei

  DOI：10.1055/s-0030-1260158

  日期：2011.10

  A green, efficient, rapid, high-yielding, catalyst-free method for the synthesis of rhodanines in water using ultrasonic irradiation is described. The procedure is straightforward and the rhodanine products are isolated by simple filtration.

  本文描述了一种绿色、高效、快速、高产、无催化剂的超声波辐射法，用于在水中合成罗丹宁。该方法操作简单，罗丹宁产品可通过简单过滤进行分离。
• The use of κ-carrageenan/Fe3O4 nanocomposite as a nanomagnetic catalyst for clean synthesis of rhodanines
  作者：Sadegh Rostamnia、Behzad Zeynizadeh、Esmail Doustkhah、Ali Baghban、Khadijeh Ojaghi Aghbash

  DOI：10.1016/j.catcom.2015.05.002

  日期：2015.8

  In this work, magnetically separable Fe3O4 nanoparticles were synthesized in the presence of natural K-carrageenan (KCAR) biopolymer to provide Fe3O4@KCAR. FT-IR analysis, scanning electron microscopy (SEM), X-ray diffraction, VSM analysis, and SEM-EDAX were incorporated for the characterization of Fe3O4@KCAR nanocomposite. And then, the first catalytic report of Fe3O4@KCAR with no post-modification was achieved by studying its catalytic activity in the multicomponent reaction of rhodanine synthesis. Based on this study, Fe3O4@KCAR was an efficient, magnetically separable and recyclable, water-dispersible and green catalyst with natural source. This catalyst also showed 9-run recyclability with no significant yield decrease. (C) 2015 Elsevier B.V. All rights reserved.
• Cetyltrimethylammonium bromide-surfactant aqueous micelles as a green and ultra-rapid reactor for synthesis of 5-oxo-2-thioxo-2,5-dihydro-3-thiophenecarboxylate derivatives
  作者：Sadegh Rostamnia、Ziba Karimi、Mehdi Ghavidel

  DOI：10.1080/17415993.2012.662980

  日期：2012.6

  Aqueous cetyltrimethylammonium bromide-surfactant micelles were found to be an efficient and rapid reactor system for the synthesis of rhodanine by a three-component reaction of amine, carbon disulfide, and activated acetylene. The advantages of this method are the use of a water medium and a simple and easy workup resulting in a green and direct synthetic method to give excellent yields of rhodanine derivatives.
• Hexafluoroisopropanol dispersed into the nanoporous SBA-15 (HFIP/SBA-15) as a rapid, metal-free, highly reusable and suitable combined catalyst for domino cyclization process in chemoselective preparation of alkyl rhodanines
  作者：Sadegh Rostamnia、Esmail Doustkhah、Ayat Nuri

  DOI：10.1016/j.jfluchem.2013.05.025

  日期：2013.9

  Hexafluoroisopropanol dispersed catalytically amount of SBA-15 (HFIP/SBA-15) with organic substrate was found to be an efficient, ultra-fast and waste-free approach for the synthesis of the biologically and pharmaceutically interesting alkyl rhodanines. The advantages of the present method are low catalyst loading, simple procedure, waste-free and direct synthetic entry to excellent yield of rhodanines, high reusability of the catalyst, and short reaction time. Also, the reaction can be performed without activation and modification of the substrates under the neutral conditions. The solid SBA-15 and HFIP could be recovered and reused for recycling. (C) 2013 Elsevier B.V. All rights reserved.