3-[2-[Tert-butyl(dimethyl)silyl]ethynyl]-5-chloro-2-(methoxymethoxymethyl)cyclohexa-2,5-diene-1,4-dione | 1239333-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[2-[Tert-butyl(dimethyl)silyl]ethynyl]-5-chloro-2-(methoxymethoxymethyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 1239333-69-7
• 化学式: C₁₇H₂₃ClO₄Si
• 分子量: 354.906
• InChiKey: SXSMYYCUADPVJZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.23
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[2-[Tert-butyl(dimethyl)silyl]ethynyl]-5-chloro-2-(methoxymethoxymethyl)cyclohexa-2,5-diene-1,4-dione 、 高邻苯二甲酸酐 在 lithium diisopropyl amide 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 以58%的产率得到3-((tert-butyldimethylsilyl)ethynyl)-9-hydroxy-2-((methoxymethoxy)methyl)-1,4-anthraquinone
  参考文献：
  名称：

  Synthetic Studies on Lactonamycins: Synthesis of the Model BCDEF Aglycon

  摘要：

  The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.

  DOI：

  10.1021/jo100913s
• 作为产物：
  描述：

  3-((tert-butyldimethylsilyl)ethynyl)-1-chloro-2,5-dimethoxy-4-((methoxymethoxy)methyl)benzene 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以85%的产率得到3-[2-[Tert-butyl(dimethyl)silyl]ethynyl]-5-chloro-2-(methoxymethoxymethyl)cyclohexa-2,5-diene-1,4-dione
  参考文献：
  名称：

  Synthetic Studies on Lactonamycins: Synthesis of the Model BCDEF Aglycon

  摘要：

  The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.

  DOI：

  10.1021/jo100913s

文献信息

• Synthetic Studies on Lactonamycins: Synthesis of the Model BCDEF Aglycon
  作者：Kana Watanabe、Yusuke Iwata、Satoshi Adachi、Tomoyuki Nishikawa、Yuko Yoshida、Shunsuke Kameda、Mitsuaki Ide、Yoko Saikawa、Masaya Nakata

  DOI：10.1021/jo100913s

  日期：2010.8.20

  The lactonamycin model aglycon 4 was synthesized from the trihalogenated benzene derivative 10. Ethynyltetraol 6 was prepared from 10 via carbon elongations, oxidative demethylation, a cycloaddition reaction with the diene derived from homophthalic anhydride, and dihydroxylation. Final E- and F-ring constructions from 6 were realized via a palladium-catalyzed cyclization-methoxycarbonylation, a stereoselective methanol addition, and lactonization, leading to the production of 4.