1'.4':7,12-di-o-benzeno-1',4',7,12-tetrahydro-5,6-naphthotetraphene-1,4-dione | 127032-75-1

• 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: 1'.4':7,12-di-o-benzeno-1',4',7,12-tetrahydro-5,6-naphthotetraphene-1,4-dione
• 英文别名: Decacyclo[18.6.6.64,11.02,19.03,12.05,10.013,18.021,26.027,32.033,38]octatriaconta-2,5,7,9,12,15,18,21,23,25,27,29,31,33,35,37-hexadecaene-14,17-dione
• CAS: 127032-75-1
• 化学式: C₃₈H₂₂O₂
• 分子量: 510.591
• InChiKey: ABQNCCFKZBSJLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  40
• 可旋转键数：
  0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1'.4':7,12-di-o-benzeno-1',4',7,12-tetrahydro-5,6-naphthotetraphene-1,4-dione 、 1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl 以 xylene 为溶剂， 反应 12.0h， 以94%的产率得到Nonadecacyclo[38.6.6.64,11.617,24.627,34.02,39.03,12.05,10.013,38.015,36.016,25.018,23.026,35.028,33.041,46.047,52.053,58.059,64.065,70]heptaconta-2,5,7,9,12,18,20,22,25,28,30,32,38,41,43,45,47,49,51,53,55,57,59,61,63,65,67,69-octacosaene-14,37-dione
  参考文献：
  名称：

  Synthesis of supertriptycene and two related iptycenes

  摘要：

  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.

  DOI：

  10.1021/jo00024a037
• 作为产物：
  描述：

  3-chloro-1,4,1',4'-tetrahydro-1,4:1',4'-di-o-benzeno-2,2'-binaphthyl 、 对苯醌 以 xylene 为溶剂， 反应 36.0h， 以86%的产率得到1'.4':7,12-di-o-benzeno-1',4',7,12-tetrahydro-5,6-naphthotetraphene-1,4-dione
  参考文献：
  名称：

  Synthesis of supertriptycene and two related iptycenes

  摘要：

  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.

  DOI：

  10.1021/jo00024a037

文献信息

• Supertriptycene, C104H62
  作者：Khalil Shahlai、Harold Hart

  DOI：10.1021/ja00165a080

  日期：1990.4
• SHAHLAI, KHALIL;HART, HAROLD, J. AMER. CHEM. SOC., 112,(1990) N, C. 3687-3688
  作者：SHAHLAI, KHALIL、HART, HAROLD

  DOI：——

  日期：——
• 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.