3-phenyl-3-hydroxy-dithioacrylic acid ethyl ester | 503469-13-4

• 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: 3-phenyl-3-hydroxy-dithioacrylic acid ethyl ester
• 英文别名: ethyl 3-phenyl-3-hydroxy-dithioacrylate；Ethyl beta-hydroxydithiocinnamate；ethyl 3-hydroxy-3-phenylprop-2-enedithioate
• CAS: 503469-13-4
• 化学式: C₁₁H₁₂OS₂
• 分子量: 224.348
• InChiKey: YRMOZMYJAMPKHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-phenyl-3-hydroxy-dithioacrylic acid ethyl ester 在 N-氯代丁二酰亚胺 作用下， 以 二甲基亚砜 为溶剂， 反应 0.17h， 以87%的产率得到diethyl 2,3-dibenzoylbutanebis(dithioate)
  参考文献：
  名称：

  室温下α-烯丙基二硫酯的无金属试剂依赖性SS和CC均偶联：通过化学选择性Paal-Knorr方法直接获得完全取代的对称噻吩

  摘要：

  AbstractAn unprecedented metal‐free oxidative homodimerization of α‐enolic dithioesters has been achieved for the first time at room temperature within 5–10 min. Molecular iodine promotes the SS coupling leading to S,S′‐bis(dithioacetals), while N‐chlorosuccinimide facilitates CC coupling to give α,α′‐bis(β‐oxo dithioesters) in good to excellent yields. Furthermore, the newly generated α,α′‐bis(β‐oxo dithioesters) have been directly employed in the synthesis of fully substituted thiophenes with a unique symmetrical substitution pattern in a one‐pot, two‐step reaction sequence.magnified image

  DOI：

  10.1002/adsc.201400828

文献信息

• Iron-Promoted Domino Annulation of α-Enolic Dithioesters with Ninhydrin under Solvent-Free Conditions: Chemoselective Direct Access to Indeno[1,2-<i>b</i>]thiophenes
  作者：Suvajit Koley、Sushobhan Chowdhury、Tanmoy Chanda、B. Janaki Ramulu、Ganesh Chandra Nandi、Maya Shankar Singh

  DOI：10.1002/ejoc.201402276

  日期：2014.9

  An efficient, straightforward, and highly chemoselective strategy has been devised for the synthesis of a broad range of indeno[1,2-b]thiophenes through the annulation of α-enolic dithioesters with ninhydrin under solvent-free conditions. The advantages of this nucleophilic domino substitution/cyclization sequence are highlighted by the use of inexpensive and readily available FeCl3·6H2O as the catalyst

  通过在无溶剂条件下将 α-烯醇二硫酯与茚三酮环化，设计了一种有效、直接且高度化学选择性的策略，用于合成广泛的茚并 [1,2-b] 噻吩。这种亲核多米诺取代/环化序列的优点通过使用廉价且容易获得的 FeCl3·6H2O 作为催化剂、操作简单、反应时间短、其官能团耐受性以及伴随形成 C- C 和 C-S 键在一次操作中得到一个噻吩环。该方法在步骤数量方面是经济的，并且是一种不含有毒试剂和溶剂的一锅式碳高效工艺。重要的是，一种新合成的茚[1,
• Acid-Controlled Chemodivergent Synthesis of Three Differently Substituted Quinolines<i>via</i>Site Selective Coupling of<i>ortho</i>- Aminoaryl Ketones with α-Enolic Dithioesters
  作者：Suvajit Koley、Tanmoy Chanda、B. Janaki Ramulu、Sushobhan Chowdhury、Maya Shankar Singh

  DOI：10.1002/adsc.201500962

  日期：2016.4.14

  straightforward approach for the chemodivergent synthesis of quinolines is described through site‐selective coupling of ortho‐aminoaryl ketones with α‐enolic dithioesters (DTEs) under solvent‐free conditions. The operationally and user‐simple one‐pot methodology is based on the trifunctional nature of DTEs. Both the carbonyl and the thiocarbonyl moiety in α‐enolic dithioesters were employed for the efficient

  通过在无溶剂条件下将邻氨基芳基酮与α-烯丙基二硫代酯（DTE）进行位点选择性偶联，描述了一种喹啉化学发散合成的简单方法。操作简便，用户简单的一站式方法基于DTE的三功能性质。仅通过改变易于处理的酸催化剂，即可将α-烯丙基二硫代酸酯中的羰基和硫代羰基部分用于以化学选择性方式高效构建三种不同取代的喹啉。
• Eco-efficient, regioselective and rapid access to 4,5-disubstituted 1,2,3-thiadiazoles via [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide under solvent-free conditions
  作者：Maya Shankar Singh、Anugula Nagaraju、Girijesh Kumar Verma、Gaurav Shukla、Rajiv Kumar Verma、Abhijeet Srivastava、Keshav Raghuvanshi

  DOI：10.1039/c3gc37047j

  日期：——

  An efficient, sustainable, and regioselective one-pot synthesis of hitherto unreported 4-aroyl/hetaroyl/alkanoyl-5-alkyl/allyl/benzylsulfanyl-1,2,3-thiadiazoles has been achieved by [3 + 2] cycloaddition of α-enolicdithioesters with tosyl azide through cascade 1–2 (S–N) and 3–4 (C–N) bond connections involving Wolff-type heterocyclization. Optimally, the reactions are very fast and completed within 2–15 minutes, when a mixture of α-enolicdithioester and tosyl azide was stirred at 0 °C in the presence of Et3N under solvent-free conditions. Furthermore, no co-catalyst or activator is necessary. The eco-compatibility, mild conditions, excellent yields, easy purification, and avoidance of expensive/toxic reagents are advantages of this protocol to access this medicinally privileged substructure.

  通过 α 的 [3 + 2] 环加成，实现了迄今为止未报道的 4-芳酰基/杂酰基/烷酰基-5-烷基/烯丙基/苄基硫基-1,2,3-噻二唑的高效、可持续和区域选择性一锅法合成-烯醇二硫酯与甲苯磺酰叠氮通过级联 1–2 (S–N) 和 3–4 (C–N) 键连接，涉及 Wolff 型杂环化。最理想的是，当α-烯醇二硫酯和甲苯磺酰叠氮化物的混合物在无溶剂条件下、Et3N存在下于0℃搅拌时，反应非常快并在2-15分钟内完成。此外，不需要助催化剂或活化剂。生态相容性、温和的条件、优异的产量、易于纯化和避免昂贵/有毒试剂是该协议获得这种医学上特权子结构的优点。
• Ligand- and Base-Free Cu^II-Mediated Selective<i>S</i>-Arylation of α-Enolic Dithioesters by Chan-Lam Coupling at Room Temperature
  作者：Suvajit Koley、Sushobhan Chowdhury、Tanmoy Chanda、B. Janaki Ramulu、Namrata Anand、Maya Shankar Singh

  DOI：10.1002/ejoc.201403171

  日期：2015.1

  achieved at room temperature under aerobic neutral conditions to afford unsymmetrical α-oxoketene S,S-acetals for the first time. This operationally simple, mild protocol tolerates a wide range of arylboronic acids and α-enolic dithioesters. Typical features of this novel strategy include short reaction times (5 min), good yields and highly selective C=S functionalization leading to S-arylation in one pot

  在室温下，在有氧中性条件下实现了芳基硼酸与 α-烯醇二硫酯的无配体和无碱铜 (II) 介导的 Chan-Lam 交叉偶联，以提供不对称的 α-氧代烯酮 S,S-缩醛，用于第一次。这种操作简单、温和的方案可耐受各种芳基硼酸和 α-烯醇二硫酯。这种新策略的典型特征包括反应时间短（5 分钟）、良好的产率和高选择性的 C=S 官能化，从而在一锅中实现 S-芳基化。
• Highly Cytotoxic Osmium(II) Compounds and Their Ruthenium(II) Analogues Targeting Ovarian Carcinoma Cell Lines and Evading Cisplatin Resistance Mechanisms
  作者：Jana Hildebrandt、Norman Häfner、Daniel Kritsch、Helmar Görls、Matthias Dürst、Ingo B. Runnebaum、Wolfgang Weigand

  DOI：10.3390/ijms23094976

  日期：——

  promising results, specifically a high cancer selective cytotoxicity and evasion of resistance mechanisms for Ru(II) and Os(II) compounds. Histone γH2AX foci and FACS experiments validated the high cytotoxicity but revealed diminished DNA damage-inducing activity and an absence of cell cycle disturbance thus pointing to another mode of action. (4) Conclusion: Ru(II) and Os(II) compounds with O,S-bidentate ligands

  (1) 背景：钌和锇络合物作为下一代抗癌药物越来越受到关注。着眼于这类化合物的构效关系，我们报告了 17 种不同的钌 (II) 配合物和四种有希望的锇 (II) 类似物，其中肉桂酸衍生物作为 O,S 双齿配体。本研究的目的是确定这些化合物的抗癌活性和逃避铂耐药机制的能力。(2) 方法：结构表征和稳定性测定采用标准技术进行，包括核磁共振光谱和 X 射线晶体学。所有复合物和单一配体都经过了对两种卵巢癌细胞系（A2780、SKOV3）及其顺铂耐药同基因细胞培养物的细胞毒活性测试，一种肺癌细胞系 (A549) 以及在体外三种非癌细胞培养物中选择的化合物。FACS 分析和组蛋白 γH2AX 染色分别用于细胞周期分布和细胞死亡或 DNA 损伤分析。(3) 结果：IC50 值显示出有希望的结果，特别是对Ru(II) 和Os(II) 化合物的高癌症选择性细胞毒性和逃避耐药机制。组蛋白 γH2AX 病灶和 FACS