(5,8-dioxospiro[2,3-dihydro-1H-naphthalene-4,3'-2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene]-8'-yl) 2,2,2-trichloroacetate | 235792-75-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (5,8-dioxospiro[2,3-dihydro-1H-naphthalene-4,3'-2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene]-8'-yl) 2,2,2-trichloroacetate
• CAS: 235792-75-3
• 化学式: C₂₂H₁₃Cl₃O₆
• 分子量: 479.701
• InChiKey: MKMFOFXUPFPYEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (5,8-dioxospiro[2,3-dihydro-1H-naphthalene-4,3'-2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene]-8'-yl) 2,2,2-trichloroacetate 在 palladium diacetate 、 lithium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 lithium methanolate 、 水 、 双氧水 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 乙醚 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 23.75h， 生成 (1S,2R,4S,12S,13R)-7,13-dimethoxy-3,11,21,22-tetraoxaheptacyclo[10.9.1.11,6.112,16.02,4.010,24.020,23]tetracosa-6,8,10(24),16(23),17,19-hexaene-5,15-dione
  参考文献：
  名称：

  Total Syntheses of (±)-Preussomerins G and I

  摘要：

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.

  DOI：

  10.1021/ol990020+
• 作为产物：
  描述：

  5,8-二甲氧基-1-四氢萘酮 在 ammonium cerium(IV) nitrate 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 对甲苯磺酸 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 、 苯 为溶剂， 反应 82.5h， 生成 (5,8-dioxospiro[2,3-dihydro-1H-naphthalene-4,3'-2,4-dioxatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaene]-8'-yl) 2,2,2-trichloroacetate
  参考文献：
  名称：

  Total Syntheses of (±)-Preussomerins G and I

  摘要：

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.

  DOI：

  10.1021/ol990020+

文献信息

• Total Syntheses of (±)-Preussomerins G and I
  作者：Shannon Chi、Clayton H. Heathcock

  DOI：10.1021/ol990020+

  日期：1999.7.1

  Preussomerins G and I (2 and 3) have been synthesized for the first time. The key reaction in the synthesis is a possibly biomimetic tautomerization reaction depicted in Scheme 3 and the foregoing graphic. The driving force for this interesting rearrangement is primarily derived from the increase in resonance energy associated with converting a naphthalene ring into two isolated benzene rings.