2,3-dicarbomethoxy-9,10-diphenyl-1,4-etheno-1,4-dihydroanthracene | 70744-54-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 2,3-dicarbomethoxy-9,10-diphenyl-1,4-etheno-1,4-dihydroanthracene
• 英文别名: 9,10-Diphenyl-1,4-(1,2-bis-methoxycarbonyl-vinyliden)-1,4-dihydro-anthracen；1,4-etheno-1,4-dihydro-11,12-bis(methoxycarbonyl)-9,10-diphenyl-anthracene；1,4-Ethenoanthracene-2,3-dicarboxylic acid, 1,4-dihydro-9,10-diphenyl-, dimethyl ester；dimethyl 3,10-diphenyltetracyclo[10.2.2.02,11.04,9]hexadeca-2,4,6,8,10,13,15-heptaene-13,14-dicarboxylate
• CAS: 70744-54-6
• 化学式: C₃₂H₂₄O₄
• 分子量: 472.54
• InChiKey: CTZXPLCEOREWTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  2,3-dicarbomethoxy-9,10-diphenyl-1,4-etheno-1,4-dihydroanthracene 在 正丁基锂 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以80%的产率得到2,3-bis(hydroxymethyl)-9,10-diphenyl-1,4-etheno-1,4-dihydroanthracene
  参考文献：
  名称：

  Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes

  摘要：

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.

  DOI：

  10.1021/jo00003a019

文献信息

• Reduction of DMAD-anthracene adducts. Synthesis and conformations of substituted cyclodecadienes
  作者：Ashok Anantanarayan、Harold Hart

  DOI：10.1021/jo00003a019

  日期：1991.2

  A general method for reducing DMAD-anthracene adducts to the corresponding enediols is described. Thus, the ester groups of 1 were reduced without C = C reduction using the DIBAH-nBuLi ''ate'' complex to give previously unknown 2 in high yield. Analogous enediols 5-7 were similarly prepared. Base treatment of dibromide 3 and dithiol 9, both prepared from 2 by standard methods, gave conformationally rigid dithiacyclodecadiene 10. With o-, m-, and p-xylylenedithiols, dibromide 3 gave respectively the conformationally labile cyclophanes 12 and 13 and the rigid cyclophane 14. Tetrabromide 16 and dithiol 9 gave cuppedophane 17, but tetrabromide 18 and 9 formed bis-m-cyclophane 19 instead.