1,4<1',2'>-benzeno-1,4-dihydro-2-ethenylnaphthalene | 136954-35-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4<1',2'>-benzeno-1,4-dihydro-2-ethenylnaphthalene
• 英文别名: 15-ethenyltetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene
• CAS: 136954-35-3
• 化学式: C₁₈H₁₄
• 分子量: 230.309
• InChiKey: SJSOZJDTMGYCAO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  1,4<1',2'>-benzeno-1,4-dihydro-2-ethenylnaphthalene 在 三氯化铝 作用下， 以 二氯甲烷 、 xylene 为溶剂， 反应 73.0h， 生成 5,18:9,14-di<1',2'>benzeno-5,6,6a,7,9,14,14a,14b,15,18,-decahydronaphtho<2,3-c>pentaphene-6,15-dione
  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：

  9,10-dihydro-9,10-ethano-anthracen-11-one 在 phosphorus pentoxide 作用下， 以 四氢呋喃 、 正庚烷 为溶剂， 反应 52.0h， 生成 1,4<1',2'>-benzeno-1,4-dihydro-2-ethenylnaphthalene
  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.