39,39,40-trichloro-5,6,7,12,13,18,19,20,25,26-decahydro-5,26:7,12:13,18:20,25-tetrakis([1,2]benzeno)-6,19-ethanodinaphtho[2,3-a:2',3'-c]trinaphthylene | 137199-02-1

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 39,39,40-trichloro-5,6,7,12,13,18,19,20,25,26-decahydro-5,26:7,12:13,18:20,25-tetrakis([1,2]benzeno)-6,19-ethanodinaphtho[2,3-a:2',3'-c]trinaphthylene
• CAS: 137199-02-1
• 化学式: C₇₂H₄₃Cl₃
• 分子量: 1014.49
• InChiKey: HPMCDXAHPGBYTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  17.01
• 重原子数：
  75.0
• 可旋转键数：
  0.0
• 环数：
  25.0
• sp3杂化的碳原子比例：
  0.17
• 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：

  39,39,40-trichloro-5,6,7,12,13,18,19,20,25,26-decahydro-5,26:7,12:13,18:20,25-tetrakis([1,2]benzeno)-6,19-ethanodinaphtho[2,3-a:2',3'-c]trinaphthylene 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以94%的产率得到39,40-dichloro-5,6,7,12,13,18,19,20,25,26-decahydro-5,26:7,12:13,18:20,25-tetrakis([1,2]benzeno)-6,19-ethenodinaphtho[2,3-a:2',3'-c]trinaphthylene
  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：

  三氯乙烯 、 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(39),3(12),5,7,9,13,15(36),16(25),18,20,22,26(35),28,30,32,37,41,43,45,47,49,51,53,55,57,59,61,63,65,67,69-hentriacontaene 以 various solvent(s) 为溶剂， 反应 48.0h， 以85%的产率得到39,39,40-trichloro-5,6,7,12,13,18,19,20,25,26-decahydro-5,26:7,12:13,18:20,25-tetrakis([1,2]benzeno)-6,19-ethanodinaphtho[2,3-a:2',3'-c]trinaphthylene
  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