2-(bis(methylthio)methylene)cyclopentane-1,3-dione

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 2-(bis(methylthio)methylene)cyclopentane-1,3-dione
• 英文别名: 2-[Bis(methylsulfanyl)methylidene]cyclopentane-1,3-dione
• 化学式: C₈H₁₀O₂S₂
• 分子量: 202.298
• InChiKey: AMFRDMGWCVNJQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(bis(methylthio)methylene)cyclopentane-1,3-dione 在 碳酸氢钠 、 magnesium 、 Selectfluor 作用下， 以 四氢呋喃 、 水 、 1,2-二溴乙烷 、 乙腈 为溶剂， 反应 3.5h， 生成
  参考文献：
  名称：

  Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene

  摘要：

  Two benzo analogues of cytotoxic spiromamakone A, comprising carbon atoms with the same oxidation state and unsaturation degree as those of the natural products, are synthesized and biologically evaluated. Substitution of alpha,alpha'-dioxoketene dithioacetals, derived from 1,3-cyclopentanediones with protected (2-formylphenyl)magnesium' bromide and 1,8-ffihydroxynaphthalene, followed by deprotection, generated these analogues via an intramolecular aldol reaction. The cytotoxicity of benzo analogues and synthetic intermediates against cervical carcinoma HeLa cells shows the necessity of the 4-cydopentene-1,3-dione moiety for biological activity.

  DOI：

  10.1021/acs.orglett.6b02328
• 作为产物：
  描述：

  二硫化碳 、 1,3-环戊二酮 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以92%的产率得到2-(bis(methylthio)methylene)cyclopentane-1,3-dione
  参考文献：
  名称：

  Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene

  摘要：

  Two benzo analogues of cytotoxic spiromamakone A, comprising carbon atoms with the same oxidation state and unsaturation degree as those of the natural products, are synthesized and biologically evaluated. Substitution of alpha,alpha'-dioxoketene dithioacetals, derived from 1,3-cyclopentanediones with protected (2-formylphenyl)magnesium' bromide and 1,8-ffihydroxynaphthalene, followed by deprotection, generated these analogues via an intramolecular aldol reaction. The cytotoxicity of benzo analogues and synthetic intermediates against cervical carcinoma HeLa cells shows the necessity of the 4-cydopentene-1,3-dione moiety for biological activity.

  DOI：

  10.1021/acs.orglett.6b02328

文献信息

• Synthesis of Spiromamakone A Benzo Analogues via Double Oxa-Michael Addition of 1,8-Dihydroxynaphthalene
  作者：Hirokazu Tsukamoto、Shogo Hanada、Koichi Kumasaka、Noritaka Kagaya、Miho Izumikawa、Kazuo Shin-ya、Takayuki Doi

  DOI：10.1021/acs.orglett.6b02328

  日期：2016.10.7

  Two benzo analogues of cytotoxic spiromamakone A, comprising carbon atoms with the same oxidation state and unsaturation degree as those of the natural products, are synthesized and biologically evaluated. Substitution of alpha,alpha'-dioxoketene dithioacetals, derived from 1,3-cyclopentanediones with protected (2-formylphenyl)magnesium' bromide and 1,8-ffihydroxynaphthalene, followed by deprotection, generated these analogues via an intramolecular aldol reaction. The cytotoxicity of benzo analogues and synthetic intermediates against cervical carcinoma HeLa cells shows the necessity of the 4-cydopentene-1,3-dione moiety for biological activity.
• Tailoring dynamic hydrogels by controlling associative exchange rates
  作者：Vivian Zhang、Joseph V. Accardo、Ilia Kevlishvili、Eliot F. Woods、Steven J. Chapman、Christopher T. Eckdahl、Charlotte L. Stern、Heather J. Kulik、Julia A. Kalow

  DOI：10.1016/j.chempr.2023.05.018

  日期：2023.8