methyl 3-(3-chlorophenyl)-3-oxopropanedithioate | 1429790-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-(3-chlorophenyl)-3-oxopropanedithioate
• CAS: 1429790-15-7
• 化学式: C₁₀H₉ClOS₂
• 分子量: 244.766
• InChiKey: DBRROGVUUXFAIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  methyl 3-(3-chlorophenyl)-3-oxopropanedithioate 在 亚硝酸特丁酯 作用下， 以 二甲基亚砜 为溶剂， 反应 3.0h， 以70%的产率得到1-(3-chlorophenyl)-3-(methylthio)prop-2-yn-1-one
  参考文献：
  名称：

  酮肟的异常行为：无试剂的光化学途径，到炔基硫醚。

  摘要：

  酮肟的独特性质主要用于杂环的合成。相反，它们吸收光和光电子转移过程的潜力仍然具有挑战性。控制酮肟策略的直接激发的广泛兴趣开辟了非常规的反应途径，从而使光化学分子内骨架修饰能够构成炔烃硫化物，而传统的活化是无法实现的。尽管取得了数十年的进步，但炔烃硫化物，特别是那些由极性官能团组成并衍生自可再生资源的硫化物，仍然未知。这些发现证明了从β-氧代二硫代酯中还原的酮肟对于确定反应条件的重要性。该方法使用温和的反应条件来生成激发态光还原剂，以使炔基硫醚阵列功能化。此外，使用电化学和光谱技术/实验对基本步骤的基本理解揭示了PCET途径可以实现这种转化，而所涉及的底物及其性能以及改进的经济工具则表明了该方法的翻译潜力。

  DOI：

  10.1021/acs.joc.1c00417

文献信息

• Yb(OTf)₃ catalyzed [3 + 2] annulations of D–A cyclopropanes with β-oxodithioesters: a regioselective synthesis of tetrahydrothiophenes
  作者：Shu-Wen Wang、Wei-Si Guo、Li-Rong Wen、Ming Li

  DOI：10.1039/c5ra06355h

  日期：——

  An efficient approach to synthesis tetrahydrothiophenes was developed through the reaction of β-oxodithioesters and D–A cyclopropanes catalyzed by Yb(OTf)₃. This methodology was highly regioselective.

  通过Yb(OTf)₃催化的β-氧代二硫酸酯和D-A环丙烷的反应，开发了一种合成四氢噻吩的高效方法。这种方法具有很高的区域选择性。
• Dual Roles of β-Oxodithioesters in the Copper-Catalyzed Synthesis of Benzo[<i>e</i>]pyrazolo[1,5-<i>c</i>][1,3]thiazine Derivatives
  作者：Li-Rong Wen、Wen-Kui Yuan、Ming Li

  DOI：10.1021/acs.joc.5b00288

  日期：2015.5.15

  A facile and efficient method for the chemoselective synthesis of benzo[e]pyrazolo[1,5-c][1,3]thiazine derivatives has been developed by tandem Ullmann coupling reactions of β-oxodithioesters (ODEs) with 3-(2-bromoaryl)-1H-pyrazoles in C–S bond formation manner, in which ODEs play dual roles as both a substrate and a ligand. A series of benzo[e]pyrazolo[1,5-c][1,3]thiazine derivatives were provided

  通过β-氧二硫代酯（ODEs）与3-（2-）的串联乌尔曼偶联反应，已经开发出一种简便高效的化学选择性合成苯并[ e ]吡唑并[1,5- c ] [1,3]噻嗪衍生物的方法。溴芳基）-1 H-吡唑以C–S键形成方式，其中ODE既充当底物又充当配体。在NaOH的存在下，在80°C的CH 3 CN中，以CuI为铜源，以良好的收率提供了一系列苯并[ e ]吡唑并[1,5- c ] [1,3]噻嗪衍生物。N 2气氛。
• Synthesis of thiophene derivatives through InCl3-catalyzed cyclization of β-oxodithioesters with vinyl azides
  作者：Li-Ming Zhang、Li-Rong Wen、Xing Xin、Ming Li

  DOI：10.1016/j.tetlet.2023.154463

  日期：2023.3

  A rapid and facile protocol for the synthesis of diverse thiophene derivatives via cyclization reaction of β-oxodithioesters and vinyl azides was established. This protocol is highly efficient and affording diverse β-oxodithioesters and vinyl azides in moderate to good yields.

  建立了一种通过 β-氧代二硫酯和乙烯基叠氮化物的环化反应快速简便地合成多种噻吩衍生物的方案。该协议效率高，可提供多种 β-氧代硫代酯和乙烯基叠氮化物，产量适中。
• Divergent Reactivity in the Reaction of β-Oxodithioesters and Hydroxylamine: Access to β-Ketonitriles and Isoxazoles
  作者：Jiaheng Li、Wei Ma、Wenbo Ming、Cong Xu、Na Wei、Mang Wang

  DOI：10.1021/acs.joc.5b01869

  日期：2015.11.6

  Starting from beta-oxodithioesters and hydroxylamine, two completely different transformations afford either beta-ketonitriles or isoxazoles with high chemoselectivity depending on the reaction conditions. The reaction of beta-oxodithioesters with hydroxylamine in EtOH at room temperature in daylight gave beta-ketonitriles in high yields. On the other hand, 3-methylthio-isoxazoles were efficiently obtained as the final products by heating the mixture of beta-oxodithioesters and hydroxylamine in HOAc at 90 degrees C.
• Indium/TFA-Catalyzed Synthesis of Tetracyclic [6,5,5,6] Indole Ring, via a Tandem Cycloannulation of β-Oxodithioester with Tryptamine
  作者：Thokchom Prasanta Singh、Suman Bhattarcharya、Okram Mukherjee Singh

  DOI：10.1021/ol400644m

  日期：2013.4.19

  The cycloannulation of beta-oxodithioesters and tryptamine in dichloromethane in the presence of a catalytic amount of InCl3 and TFA gave the novel 5-aryl/heteroaryl 2a(1),9b-dihydro-1H-2a,5a-diaza-cyclopenta[jk]fluorene-3(2H)-thiones in moderate to good yields. The reaction was proposed to involve a tandem transformation of thioamide, protonation, and dehydrative cyclization. KMnO4-oxidation of these newly prepared compounds yielded oxidative desulfurization products in good yields.