hexamethylhexadehydrotribenzo[12]annulene | 210567-08-1

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: hexamethylhexadehydrotribenzo[12]annulene
• 英文别名: 6,7,14,15,22,23-Hexamethyltetracyclo[18.4.0.04,9.012,17]tetracosa-1(20),4(9),5,7,12(17),13,15,21,23-nonaen-2,10,18-triyne
• CAS: 210567-08-1
• 化学式: C₃₀H₂₄
• 分子量: 384.521
• InChiKey: SRUBOVFVDUWMIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  hexamethylhexadehydrotribenzo[12]annulene 在 titanium(IV) isopropylate 、 异丙基氯化镁 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.0h， 以83%的产率得到
  参考文献：
  名称：

  Short-step syntheses and complexation properties of Z,Z-tribenzodidehydro- and all-Z-tribenzo[12]annulenes

  摘要：

  Syn theses of all/-Z-tribenzo[12]annulenes (1a-c) and Z,Z-tribenzodidehydro[12]annulenes (2a-c) by the reduction of the corresponding tribenzohexadehydro[ I 2]annulenes 3a-c were carried out using a low valent titanium complex generated from Ti(O-iPr)(4) and i-PrMgCl. The unique structure of the first reduction products 2a-c as well as la-c was fully characterized. Complexation of these annulenes with silver(l) ions produces the corresponding silver complexes. Among them, the silver complexes of 2a-c exhibit interesting monomer dimer equilibrium. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.03.044
• 作为产物：
  描述：

  1,2-二碘-4,5-二甲基苯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 (Me3CO)3W<*>CCMe3 、 三乙胺 作用下， 以 甲苯 为溶剂， 25.0~80.0 ℃ 、151.99 kPa 条件下， 反应 50.0h， 生成 hexamethylhexadehydrotribenzo[12]annulene
  参考文献：
  名称：

  Miljanić, Ognjen Š.; Vollhardt, K. Peter C.; Whitener, Glenn D., Synlett, 2003, # 1, p. 29 - 34

  摘要：

  DOI：

文献信息

• A one-step synthesis of dehydro[12]annulenes using palladium-catalyzed reaction of o-diiodoarenes with acetylene gas
  作者：Masahiko Iyoda、Anusorn Vorasingha、Yoshiyuki Kuwatani、Masato Yoshida

  DOI：10.1016/s0040-4039(98)00882-x

  日期：1998.6

  Hexadehydrotribenzo[12]annulene and its analogues were synthesized in a one-pot procedure by the palladium-catalyzed cross-coupling of o-diiodobenzene and its analogues with acetylene. The reaction proceeded smoothly to give the desired dehydro[12]annulenes in moderate yields.

  通过钯催化邻二碘代苯及其类似物与乙炔的交叉偶联，以一锅法合成了六氢三苯并[12]环戊烯及其类似物。反应平稳进行，以中等收率得到所需的脱氢[12]环戊烯。
• Copper-Mediated Simple and Efficient Synthesis of Tribenzohexadehydro[12]annulene and Its Derivatives
  作者：Masahiko Iyoda、Siriwan Sirinintasak、Yoshihiro Nishiyama、Anusorn Vorasingha、Fatema Sultana、Kazumi Nakao、Yoshiyuki Kuwatani、Haruo Matsuyama、Masato Yoshida、Yoshihiro Miyake

  DOI：10.1055/s-2004-822393

  日期：——

  A simple and efficient synthesis of tribenzohexadehydro[12]annulene and its derivatives was carried out using coupling reaction of acetylenes with iodoarenes in the presence of catalytic amounts of CuI and PPh,, together with three equivalents of K 2 CO 3 in DMF. This synthetic procedure was applied to the synthesis of a large annulenoannulene derivative.

  在催化量的 CuI 和 PPh 以及三当量的 DMF 中的 K 2 CO 3 存在下，使用乙炔与碘代芳烃的偶联反应进行了三苯并六氢[12]环烯及其衍生物的简单有效合成。该合成程序适用于合成大环烯基环烯衍生物。
• Miljanić, Ognjen Š.; Vollhardt, K. Peter C.; Whitener, Glenn D., Synlett, 2003, # 1, p. 29 - 34
  作者：Miljanić, Ognjen Š.、Vollhardt, K. Peter C.、Whitener, Glenn D.

  DOI：——

  日期：——
• Short-step syntheses and complexation properties of Z,Z-tribenzodidehydro- and all-Z-tribenzo[12]annulenes
  作者：Siriwan Sirinintasak、Yoshiyuki Kuwatani、Shin-ichi Hoshi、Eigo Isomura、Tohru Nishinaga、Masahiko Iyoda

  DOI：10.1016/j.tetlet.2007.03.044

  日期：2007.5

  Syn theses of all/-Z-tribenzo[12]annulenes (1a-c) and Z,Z-tribenzodidehydro[12]annulenes (2a-c) by the reduction of the corresponding tribenzohexadehydro[ I 2]annulenes 3a-c were carried out using a low valent titanium complex generated from Ti(O-iPr)(4) and i-PrMgCl. The unique structure of the first reduction products 2a-c as well as la-c was fully characterized. Complexation of these annulenes with silver(l) ions produces the corresponding silver complexes. Among them, the silver complexes of 2a-c exhibit interesting monomer dimer equilibrium. (c) 2007 Elsevier Ltd. All rights reserved.