5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene | 136954-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene
• 英文别名: 5,18:9,14-di[1',2']benzeno-5,9,14,18-tetrahydronaphtho[2,3-c]pentaphene；undecacyclo[22.6.6.69,16.02,23.03,20.05,18.08,17.010,15.025,30.031,36.037,42]dotetraconta-2(23),3(20),4,6,8(17),10,12,14,18,21,25,27,29,31,33,35,37,39,41-nonadecaene
• CAS: 136954-39-7
• 化学式: C₄₂H₂₆
• 分子量: 530.668
• InChiKey: UOATZQFGKPECNO-UHFFFAOYSA-N

物化性质

• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.97
• 重原子数：
  42.0
• 可旋转键数：
  0.0
• 环数：
  13.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  反-1,2-二氯乙烯 、 5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene 以 萘烷 为溶剂， 反应 48.0h， 以79%的产率得到rac-(25R,26R)-25,26-dichloro-5,6,9,14,15,18-hexahydro-5,18:9,14-bis([1,2]benzeno)-6,15-ethanonaphtho[2,3-c]pentaphene
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038
• 作为产物：
  描述：

  5,18:9,14-di<1',2'>benzeno-5,6,9,14,15,18-hexahydronaphtho<2,3-c>pentaphene-6,15-dione 在 Al(c-C6H11O)3 、 环己醇 作用下， 反应 24.0h， 以88%的产率得到5,18:9,14-di<1',2'>benzeno-5,9,14,18-tetrahydronaphtho<2,3-c>pentaphene
  参考文献：
  名称：

  Synthesis of three helically chiral iptycenes

  摘要：

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.

  DOI：

  10.1021/jo00024a038

文献信息

• Synthesis of three helically chiral iptycenes
  作者：Khalil Shahlai、Harold Hart、Abdollah Bashir-Hashemi

  DOI：10.1021/jo00024a038

  日期：1991.11

  The synthesis of iptycenes 2-4, each of which is helically chiral and has a C2 symmetry axis, is described. Key intermediates are diene 7, prepared in two steps and 44% yield from known ketone 5, and anthracene 11, prepared in four steps and 48% yield from diene 7. A noteworthy step in the latter sequence is the aluminum chloride catalyzed, room-temperature, regio- and stereoselective cycloaddition of naphthoquinone 8 to diene 7 to give a single isomer of 9. Anthracene 11 was converted in one step to 2 and in four steps to 3 (Scheme II). Bicycloalkene 15, an intermediate in the latter synthesis, was converted to 4 in two steps (Scheme III). Cycloaddition of unactivated dienophile 15 to unactivated dienes 17 and 18 proceeds in good yields. Hydrocarbon 3 could be resolved on several chiral columns.