9-(2-formyl-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene | 185068-98-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 9-(2-formyl-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene
• 英文别名: dimethyl 1-(2-methyl-4-oxobutan-2-yl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene-15,16-dicarboxylate
• CAS: 185068-98-8
• 化学式: C₂₅H₂₄O₅
• 分子量: 404.463
• InChiKey: SMZJNLCZHCCKTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-(2-formyl-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene 在 sodium chlorite 、 phosphate buffer 、 草酰氯 、 双氧水 作用下， 以 乙腈 、 苯 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  Absolute Conformation and Substituent Effects on Chiroptical Properties of 9-(2-Halo-1,1-dimethylethyl)-11,12- bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes^1,2

  摘要：

  Optically active and inactive rotational isomers of 9-(1,1-dimethyl-3-butenyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene were isolated. The absolute conformations of these optically active conformers were determined by correlating them with those of camphorsultam amides of 9-(2-carboxy-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes, the latter being determined by X-ray analysis. From the carboxylic acids, the title compounds, in which the halogen is a chloro, a bromo, or an iodo, were prepared. The CD spectra of the title compounds showed remote substituent effects on the Cotton effect at ca. 220 nm.

  DOI：

  10.1021/ja961520q
• 作为产物：
  描述：

  9-(2-甲基戊-4-烯-2-基)蒽 在 吡啶 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 、 sodium hydrogensulfite 、 过碘酸 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 9-(2-formyl-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene
  参考文献：
  名称：

  Absolute Conformation and Substituent Effects on Chiroptical Properties of 9-(2-Halo-1,1-dimethylethyl)-11,12- bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes^1,2

  摘要：

  Optically active and inactive rotational isomers of 9-(1,1-dimethyl-3-butenyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene were isolated. The absolute conformations of these optically active conformers were determined by correlating them with those of camphorsultam amides of 9-(2-carboxy-1,1-dimethylethyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes, the latter being determined by X-ray analysis. From the carboxylic acids, the title compounds, in which the halogen is a chloro, a bromo, or an iodo, were prepared. The CD spectra of the title compounds showed remote substituent effects on the Cotton effect at ca. 220 nm.

  DOI：

  10.1021/ja961520q

文献信息

• Absolute Conformation and Chiroptical Properties. VII. 9(1^′)-<b><i>Msc</i></b>and<b><i>Psc</i></b>Forms of 9-(2-Fluoro-1,1-dimethylethyl)- and 9-(1,1-Dimethylpropyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracenes
  作者：Shinji Toyota、Satoshi Yoshida、Hiroharu Kojima、Michinori Oki

  DOI：10.1246/bcsj.73.2371

  日期：2000.10

  sc-9-(2-fluoro-1,1-dimethylethyl)- and 9-(3-iodo-1,1-dimethylpropyl)-11,12-bis(methoxycarbonyl)-9,10-dihydro-9,10-ethenoanthracene were prepared by treatment of the corresponding carboxylic acid with xenon difluoride and by reduction of 9-(1,1-dimethyl-3-oxopropyl) compound followed by a reaction with iodine in the presence of imidazole, respectively. The fluoro and the iodo compounds were resolved on a chiral

  sc-9-(2-氟-1,1-二甲基乙基)-和9-(3-碘-1,1-二甲基丙基)-11,12-双(甲氧基羰基)-9,10-二氢-的外消旋形式通过用二氟化氙处理相应的羧酸和还原 9-(1,1-二甲基-3-氧代丙基) 化合物，然后在咪唑的存在下分别与碘反应来制备 9,10-乙烯蒽。氟化合物和碘化合物在手性柱上分离。这些化合物的绝对构象是通过相同的方法从已知绝对构象的羧酸和醛中推导出它们来确定的。用阮内镍在 1-丙醇中还原碘化合物，得到具有旋光活性的 sc-9-(1,1-二甲基丙基) 化合物。在 CD 光谱中，Psc-(-) 氟化合物在约 240 纳米，与其他卤素化合物类似，并且在大约 10 倍时具有更强的棉花效应。220 nm 比其他卤素化合物。Psc-(+)-9-(1,1-二甲基丙基)化合物表现出相当不同的...