3-chloro-4-((4-methoxyphenyl)thio)cyclobut-3-ene-1,2-dione | 956110-80-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-chloro-4-((4-methoxyphenyl)thio)cyclobut-3-ene-1,2-dione
• 英文别名: 3-Chloro-4-(4-methoxyphenyl)sulfanylcyclobut-3-ene-1,2-dione；3-chloro-4-(4-methoxyphenyl)sulfanylcyclobut-3-ene-1,2-dione
• CAS: 956110-80-8
• 化学式: C₁₁H₇ClO₃S
• 分子量: 254.694
• InChiKey: IUGGQUPMAGNHSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  68.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-chloro-4-((4-methoxyphenyl)thio)cyclobut-3-ene-1,2-dione 在 双(乙腈)氯化钯(II) 、 tris(dibenzylideneacetone)dipalladium (0) copper(l) iodide 、 三(2-呋喃基)膦 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 22.0h， 生成 3-[4-(Dimethylamino)phenyl]-4-(4-methoxyphenyl)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  Selective Cross-Couplings. Sequential Stille−Liebeskind/Srogl Reactions of 3-Chloro-4-arylthiocyclobutene-1,2-dione

  摘要：

  The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogi reaction conditions (in the presence of a Cu(l) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).

  DOI：

  10.1021/ol701628z
• 作为产物：
  描述：

  3,4-二氯-3-环丁烯-1,2-二酮 、 4-甲氧基苯硫酚 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以93%的产率得到3-chloro-4-((4-methoxyphenyl)thio)cyclobut-3-ene-1,2-dione
  参考文献：
  名称：

  [EN] NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI
  [FR] NOUVEAUX COMPOSÉS D'OXADIAZOLE POUR LA LUTTE OU LA PRÉVENTION CONTRE DES CHAMPIGNONS PHYTOPATHOGÈNES

  摘要：

  本发明公开了一种化合物的结构式(I)，其中，R1、L1、A、k、L2、W、L4、R5、R8和R9的定义如详细描述中所述。本发明还公开了一种制备结构式(I)化合物的方法。

  公开号：

  WO2020208509A1

文献信息

• [EN] NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI<br/>[FR] NOUVEAUX COMPOSÉS D'OXADIAZOLE POUR LA LUTTE OU LA PRÉVENTION CONTRE DES CHAMPIGNONS PHYTOPATHOGÈNES
  申请人：PI INDUSTRIES LTD

  公开号：WO2020208509A1

  公开（公告）日：2020-10-15

  The present invention discloses a compound of formula (I), wherein, R1, L1,A, k, L2, W, L4, R5, R8 and R9 are as defined in the detailed description. The present invention further discloses a process for preparing the compound of formula (I).

  本发明公开了一种化合物的结构式(I)，其中，R1、L1、A、k、L2、W、L4、R5、R8和R9的定义如详细描述中所述。本发明还公开了一种制备结构式(I)化合物的方法。
• NOVEL OXADIAZOLE COMPOUNDS FOR CONTROLLING OR PREVENTING PHYTOPATHOGENIC FUNGI
  申请人：PI Industries Ltd.

  公开号：EP3953340A1

  公开（公告）日：2022-02-16
• Synthesis and antitumor activity of novel 3,4-diaryl squaric acid analogs
  作者：Zong-ying Liu、Yue-ming Wang、Yan-xing Han、Ling Liu、Jie Jin、Hong Yi、Zhuo-rong Li、Jian-dong Jiang、David W. Boykin

  DOI：10.1016/j.ejmech.2013.04.046

  日期：2013.7

  A series of novel 3,4-diaryl squaric acid analogs 4a-r related to combretastatin A-4 (CA4) using squaric acid as the cis-restricted linker were prepared and studied for their anticancer activity against selected human cancer cell lines. New compounds 4g, 4k, 4m, 4n, 4p, 4q and 4r exhibit strong activities against human leukemia cells with IC50 values of <= 20 nM and compounds 4k, 4n, 4p, 4q and 4r showed potent activities against a panel of human tumor cell lines. Compounds 4n and 4p arrest tumor cell cycle in G2-M phase. Computational modeling analysis suggests that the binding mechanism of compound 4n to the colchicine binding site on the microtubules is similar to that of CA4. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Selective Cross-Couplings. Sequential Stille−Liebeskind/Srogl Reactions of 3-Chloro-4-arylthiocyclobutene-1,2-dione
  作者：Angélica Aguilar-Aguilar、Eduardo Peña-Cabrera

  DOI：10.1021/ol701628z

  日期：2007.10.1

  The synthesis and initial reactivity studies of 2 are described. It was found that it participates in Stille couplings exclusively at the C-Cl site with a number of organostannanes (58-71% yield) in the absence of Cu(I). Then, these new derivatives were functionalized at the C-S site with boronic acids by switching to the Liebeskind-Srogi reaction conditions (in the presence of a Cu(l) carboxylate) to yield the bifunctionalized cyclobutenediones (44-90% yield).