2-methyl-3-(4-methoxyphenyl)cyclopropenone | 26306-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-methyl-3-(4-methoxyphenyl)cyclopropenone
• 英文别名: (4-Methoxy-phenyl)-methyl-cyclopropenon；2-(4-Methoxyphenyl)-3-methylcycloprop-2-en-1-one
• CAS: 26306-99-0
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: VYTDKCMAZCBTHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(4-methoxyphenyl)cyclopropenone 在 tetrafluoroboric acid 硫代乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以87%的产率得到2-(4-Methoxy-phenyl)-3-methyl-cycloprop-2-enethione
  参考文献：
  名称：

  Synthesis of Cyclopropenethiones or 3,3-Bis[acylthio]cyclopropenes from Cyclopropenones and Thiocarboxylic Acids

  摘要：

  DOI：

  10.1055/s-1981-29323
• 作为产物：
  描述：

  3-acetoxy-1-(4-methoxyphenyl)-2-trimethylsilylpropene 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 二乙二醇二甲醚 为溶剂， 反应 0.17h， 生成 2-methyl-3-(4-methoxyphenyl)cyclopropenone
  参考文献：
  名称：

  Preparation of methylenedifluorocyclopropanes via cyclopropyl anion promoted β-elimination

  摘要：

  Preparation of methylenedifluorocyclopropanes 2 through the beta-elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C-Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure thermodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclopropylglycine (F(2)MCPG) derivative 17 is also presented. (C) 1999 Elsevier Science Ltd. All rights resented.

  DOI：

  10.1016/s0040-4020(99)00588-8

文献信息

• Cyclopropenone, Cyclopropeniminium Ion, and Cyclopropenethione as Novel Electrophilic Warheads for Potential Target Discovery of Triple-Negative Breast Cancer
  作者：Shumin Lv、Fang Xu、Youlong Fan、Ke Ding、Zhengqiu Li

  DOI：10.1021/acs.jmedchem.2c01889

  日期：2023.2.23

  currently available for drug development, triple-negative breast cancer (TNBC) has been defined as one of the most difficult diseases for chemotherapy. Herein, we describe a suite of novel electrophilic warheads, which we have used in chemical proteomics studies in a search for potential targets for TNBC. Binding site analysis revealed that these warheads can modify not only highly nucleophilic residues

  由于目前可用于药物开发的靶点非常少，三阴性乳腺癌（TNBC）被定义为最难化疗的疾病之一。在此，我们描述了一套新型亲电子弹头，我们已将其用于化学蛋白质组学研究，以寻找 TNBC 的潜在靶标。结合位点分析表明，这些弹头不仅可以修饰高度亲核的残基，包括半胱氨酸和赖氨酸，还可以修饰弱亲核的残基。Kirsten 大鼠肉瘤的 Cys12 (KRAS G12C) 被环丙烯酮和环丙烯亚胺离子成功标记。这些新型的基于亲电试剂的探针实现了对 TNBC 细胞的适度抑制活性。基于活性的蛋白质分析表明，这些亲电子试剂可以共价标记一系列必需的蛋白质靶标，包括来自 MDA-MB-231 细胞的 ALDH2、LRPPRC 和 FABP5。进一步的功能验证实验表明 FABP5 可能是 TNBC 的潜在目标。
• YOSHIDA HIROSHI; NAKAJIMA MIKITO; OGATA TSUYOSHI, SYNTHESIS, 1981, NO 1, 36-38
  作者：YOSHIDA HIROSHI、 NAKAJIMA MIKITO、 OGATA TSUYOSHI

  DOI：——

  日期：——
• Synthesis of Cyclopropenethiones or 3,3-Bis[acylthio]cyclopropenes from Cyclopropenones and Thiocarboxylic Acids
  作者：Hiroshi Yoshida、Mikito Nakajima、Tsuyoshi Ogata

  DOI：10.1055/s-1981-29323

  日期：——
• Preparation of methylenedifluorocyclopropanes via cyclopropyl anion promoted β-elimination
  作者：Akira Shibuya、Midori Okada、Yuko Nakamura、Mie Kibashi、Hiroaki Horikawa、Takeo Taguchi

  DOI：10.1016/s0040-4020(99)00588-8

  日期：1999.8

  Preparation of methylenedifluorocyclopropanes 2 through the beta-elimination reaction promoted by difluorocyclopropyl anion formed by cleavage of C-Si bond with TBAF is described. Base-catalyzed isomerization of 2 to difluorocyclopropene 11 shows the latter structure thermodynamically more stable in contrast to non-fluorinated cases. Application of this method to the synthesis of methylenedifluorocyclopropylglycine (F(2)MCPG) derivative 17 is also presented. (C) 1999 Elsevier Science Ltd. All rights resented.