13-(1-Hydroxyethyl)tetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,17,19-hexaen-12-ol | 405226-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 13-(1-Hydroxyethyl)tetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,17,19-hexaen-12-ol
• CAS: 405226-07-5
• 化学式: C₂₂H₂₆O₂
• 分子量: 322.447
• InChiKey: ALOPBGLOVUIVBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-(1-Hydroxyethyl)tetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,17,19-hexaen-12-ol 在 吡啶 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 5.0h， 生成 5-ethenyl-6,7-dihydro[2.2](1,4)naphthalenoparacyclophane
  参考文献：
  名称：

  The Preparation of Helical Cyclophanes Containing Five-membered Rings

  摘要：

  Cycloadditions between the indenone derivatives prepared in situ from the bromides 12a and 12b and 4-vinyl[2.2]paracyclophane (11) yielded the Diels-Alder adducts 13a and 13b in acceptable yields. When these were heated in the presence of DDQ in toluene, the fluorenophanes 14a and 14b were produced in good yields. The diol 17 obtained from the tetralonophane 15 on treatment with POCl3/pyridine was dehydrated to the diene 18, which could be trapped by p-benzoquinone (19) to provide the cycloadducts 20 and 21; the former was oxidized to the latter by DDQ treatment. Although the even more highly annelated helical phane system 22 could be prepared from 17 and 12a, its aromatization to the ketone 24 or the hydrocarbon 25 failed. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations. A single-crystal X-ray structure analysis for the parent hydrocarbon phenanthreno[2.2]paracyclophane (5) is reported.

  DOI：

  10.1002/1099-0690(200111)2001:22<4259::aid-ejoc4259>3.0.co;2-i
• 作为产物：
  描述：

  5,5-Difluoro-7-methyl-6-oxa-4-oxonia-5-boranuidapentacyclo[10.8.2.215,18.02,11.03,8]tetracosa-1,3,7,11,15,17,21,23-octaene 在 sodium tetrahydroborate 作用下， 以 乙醇 、 水 为溶剂， 反应 2.5h， 以98%的产率得到13-(1-Hydroxyethyl)tetracyclo[8.6.2.24,7.011,16]icosa-1(16),4,6,10,17,19-hexaen-12-ol
  参考文献：
  名称：

  The Preparation of Helical Cyclophanes Containing Five-membered Rings

  摘要：

  Cycloadditions between the indenone derivatives prepared in situ from the bromides 12a and 12b and 4-vinyl[2.2]paracyclophane (11) yielded the Diels-Alder adducts 13a and 13b in acceptable yields. When these were heated in the presence of DDQ in toluene, the fluorenophanes 14a and 14b were produced in good yields. The diol 17 obtained from the tetralonophane 15 on treatment with POCl3/pyridine was dehydrated to the diene 18, which could be trapped by p-benzoquinone (19) to provide the cycloadducts 20 and 21; the former was oxidized to the latter by DDQ treatment. Although the even more highly annelated helical phane system 22 could be prepared from 17 and 12a, its aromatization to the ketone 24 or the hydrocarbon 25 failed. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations. A single-crystal X-ray structure analysis for the parent hydrocarbon phenanthreno[2.2]paracyclophane (5) is reported.

  DOI：

  10.1002/1099-0690(200111)2001:22<4259::aid-ejoc4259>3.0.co;2-i

文献信息

• The Preparation of Helical Cyclophanes Containing Five-membered Rings
  作者：Assunta Marrocchi、Lucio Minuti、Aldo Taticchi、Ina Dix、Henning Hopf、Eszter Gacs-Baitz、Peter G. Jones

  DOI：10.1002/1099-0690(200111)2001:22<4259::aid-ejoc4259>3.0.co;2-i

  日期：2001.11

  Cycloadditions between the indenone derivatives prepared in situ from the bromides 12a and 12b and 4-vinyl[2.2]paracyclophane (11) yielded the Diels-Alder adducts 13a and 13b in acceptable yields. When these were heated in the presence of DDQ in toluene, the fluorenophanes 14a and 14b were produced in good yields. The diol 17 obtained from the tetralonophane 15 on treatment with POCl3/pyridine was dehydrated to the diene 18, which could be trapped by p-benzoquinone (19) to provide the cycloadducts 20 and 21; the former was oxidized to the latter by DDQ treatment. Although the even more highly annelated helical phane system 22 could be prepared from 17 and 12a, its aromatization to the ketone 24 or the hydrocarbon 25 failed. All new compounds were characterized by their spectroscopic data, in particular by extensive NMR investigations. A single-crystal X-ray structure analysis for the parent hydrocarbon phenanthreno[2.2]paracyclophane (5) is reported.