1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl | 120524-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl
• 英文别名: 15-(15-Tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaenyl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13,15-heptaene
• CAS: 120524-15-4
• 化学式: C₃₂H₂₂
• 分子量: 406.527
• InChiKey: PPCCQFMLYUQDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl 在 硫酸 作用下， 以 乙酸酐 、 xylene 为溶剂， 反应 8.17h， 生成 5,6,11,11a,17b,18-hexahydro-5,18:6,11-di-o-benzenotrinaphthylene
  参考文献：
  名称：

  A method for the synthesis of angular iptycenes

  摘要：

  DOI：

  10.1021/jo00272a031
• 作为产物：
  描述：

  3-chloro-1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl 在 magnesium 、 碘甲烷 作用下， 以 四氢呋喃 为溶剂， 以91%的产率得到1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl
  参考文献：
  名称：

  A method for the synthesis of angular iptycenes

  摘要：

  DOI：

  10.1021/jo00272a031

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.
• Synthesis of supertriptycene and two related iptycenes
  作者：Khalil Shahlai、Harold Hart

  DOI：10.1021/jo00024a037

  日期：1991.11

  A 10-step 23-30% overall yield synthesis of supertriptycene (2) from vinyl chloride 5 is described. Anthracene 3 is the key intermediate, prepared from 5 in six steps and 41-53% yield (Scheme II). trans-1,2-Dichloroethene adds to 3 to give adduct 22 (94%), which is then converted to 2 in three steps and 70% yield (Scheme IV). A key step in the latter sequence is the remarkable cycloaddition of unactivated alkene 26 to hindered diene 4 in excellent yield. Supertriptycene (2), C104H62, shows only seven peaks in its H-1 NMR spectrum and 12 peaks in its C-13 NMR spectrum, consistent with its D3h symmetry. The hydrocarbon is stable to well over 500-degrees-C. Anthracene 3 was also converted to undecaiptycene 12 and to tridecaiptycene 16; the latter was also independently synthesized in two steps from alkene 26 and diene 28.
• Supertriptycene, C104H62
  作者：Khalil Shahlai、Harold Hart

  DOI：10.1021/ja00165a080

  日期：1990.4
• SHAHLAI, KHALIL;HART, HAROLD, J. ORG. CHEM., 54,(1989) N1, C. 2615-2620
  作者：SHAHLAI, KHALIL、HART, HAROLD

  DOI：——

  日期：——
• SHAHLAI, KHALIL;HART, HAROLD, J. AMER. CHEM. SOC., 112,(1990) N, C. 3687-3688
  作者：SHAHLAI, KHALIL、HART, HAROLD

  DOI：——

  日期：——