3-(2-bromophenyl)-3-oxo-N-phenylpropanethioamide | 1258214-89-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-(2-bromophenyl)-3-oxo-N-phenylpropanethioamide
• CAS: 1258214-89-9
• 化学式: C₁₅H₁₂BrNOS
• 分子量: 334.236
• InChiKey: YNHNZDXBGDETPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  29.1
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(2-bromophenyl)-3-oxo-N-phenylpropanethioamide 在 copper(l) iodide 、 hydrazine hydrate 、 2-(Diacetylmethylene)imidazolidine 、 sodium hydroxide 作用下， 以 乙醇 、 二甲基亚砜 为溶剂， 反应 3.5h， 生成 5-amino-2-(phenylamino)pyrazolo[5,1-a]isoquinoline-6-carboxamide
  参考文献：
  名称：

  铜催化串联反应合成杂环乙酮缩醛为配体的吡唑并[5,1- a ]异喹啉

  摘要：

  CuI催化5-（2-溴芳基）-N-芳基-1 H-吡唑-3-胺与活性乙腈衍生物的串联反应，以良好的产率制备了吡唑并[5,1- a ]异喹啉在温和条件下使用杂环烯酮缩醛（HKA）作为新的配体进行开发。这是HKA首次用作铜催化偶联反应的配体。

  DOI：

  10.1021/jo5020323

文献信息

• Electrochemical Selective Oxidative Synthesis of Diversified Sulfur Heterocycles from <scp>β‐Ketothioamides</scp>
  作者：Li‐Rong Wen、Ning‐Ning Wang、Wu‐Bo Du、Ming‐Zhe Zhu、Chao Pan、Lin‐Bao Zhang、Ming Li

  DOI：10.1002/cjoc.202100132

  日期：2021.7

  diversified sulfur heterocycles has been described through organic electrosynthesis means. In undivided cell, dihydrothiophenes, thiazolines and 1,4-dithiines could be easily generated from various available β-ketothioamides under metal-free and external oxidant-free conditions. The transformation underwent smoothly under mild conditions and could be easily scaled-up. Moreover, different sulfur heterocycles

  通过有机电合成方法描述了构建多样化硫杂环的通用实用方案。在未分裂的细胞中，在无金属和无外部氧化剂的条件下，可以从各种可用的 β-酮硫酰胺中轻松生成二氢噻吩、噻唑啉和 1,4-二硫嘌呤。转型在温和的条件下顺利进行，并且很容易扩大规模。此外，通过不同的溶剂产生不同的硫杂环，1,4-二氮杂双环[2.2.2]辛烷（DABCO）可以实现这种转化的氢原子转移（HAT）过程。
• Synthesis of pyrrole disulfides <i>via</i> umpolung of β-ketothioamides
  作者：Xiangrui Meng、Weisi Guo、Guangming Nan、Ming Li

  DOI：10.1039/d2ob01506d

  日期：——

  Na2CO3-promoted reaction of β-ketothioamides (KTAs) and cyanoacetates was developed for the synthesis of pyrrole disulfides using air as a green oxidant. This protocol features a broad substrate scope and mild reaction conditions. Preliminary mechanistic studies indicate that the reaction involves a tandem unusual umpolung of KTAs, N-cyclization, tautomerization and oxidative coupling process.

  使用空气作为绿色氧化剂，开发了一种 Na 2 CO 3促进的 β-酮硫代酰胺 (KTA) 和氰基乙酸盐的反应，用于合成吡咯二硫化物。该协议具有广泛的底物范围和温和的反应条件。初步的机理研究表明，该反应涉及 KTA 的串联不寻常 umpolung、N-环化、互变异构和氧化偶联过程。
• TBHP‐Mediated Intermolecular Radical Coupling and Intramolecular Cyclization Cascade: Access to Furo[2,3‐<i>b</i>]quinoxalines and Their Photophysical Study
  作者：Subhasish Ray、Vipin Kumar、Saurabh Singh、Krishanu Bandyopadhyay、Satyen Saha、Maya Shankar Singh

  DOI：10.1002/adsc.202301045

  日期：2024.1.30

  accessible β-ketothioamides and quinoxalin-2-ones in open flask at room temperature under TBHP mediated conditions. Mechanistic studies revealed that the overall reactivity relies on the seamless integration of intermolecular radical coupling and intramolecular cyclization via desulfhydration of C=S bond cleavage. Generation of H2S as the only by-product makes this process highly attractive. Furthermore

  我们设计了一种级联一锅法策略，在室温下、TBHP 介导的条件下，在敞口烧瓶中，用易于获得的 β-酮硫酰胺和喹喔啉-2-酮构建 31 个呋喃稠合喹喔啉实例，产率高达 88%。机理研究表明，整体反应性依赖于分子间自由基偶联和通过C=S键断裂脱硫的分子内环化的无缝整合。 H 2 S的生成作为唯一的副产品使得该过程极具吸引力。此外，还研究了呋喃稠合喹喔啉的光物理行为。
• Yb(OTf)₃-Mediated Access to Furans from β-Ketothioamides via Eschenmoser Sulfide Contraction Reaction
  作者：Ming Li、Xiang-Jing Kong、Li-Rong Wen

  DOI：10.1021/acs.joc.5b01924

  日期：2015.12.18

  A mild and straightforward synthetic protocol for construction of a Loran skeleton promoted by Yb(OTf)(3) from beta-ketothioamides and arylglyoxals has been developed at room temperature. Importantly, this protocol involves a tandem sequence that includes aldol condensation, N-cyclization, ring opening, O-cyclization, S-cyclization, and Eschenmoser sulfide contraction.
• Reactivity of Functionalized <i>N</i>,<i>S</i>-Ketene Acetal: Regioselective Construction of Tetrahydrobenzo[<i>b</i>]pyran and Chromeno[2,3-<i>b</i>]quinoline Derivatives
  作者：Ming Li、Yan-Li Hou、Li-Rong Wen、Fu-Meng Gong

  DOI：10.1021/jo101902z

  日期：2010.12.17

  Regioselective synthesis of functionalized tetrahydrobenzo[b]pyrans has been developed by multi-component reactions (MCRs) and tandem [3 + 3] annulations of beta-benzoylthioacetanilides or beta-(2-haloaroyl)thioacetanilides as valuable sources with aromatic aldehydes and 5,5-dimethy1-1,3-cyclohexanedione catalyzed by triethylamine. This MCR followed by a postcondensation cyclization via an intramolecular SNAr in the presence of K2CO3 led to an unprecedented novel chromeno-[2,3-b]quinoline framework containing an important chromene moiety in good yields. The reactions were very mild, convenient, and o-selective to form new fused tetracyclic target molecules.