benzo<4,5>cyclodec-4-ene-2,6-diyn-1-one | 146978-90-7

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: benzo<4,5>cyclodec-4-ene-2,6-diyn-1-one
• 英文别名: 4,5-benzocyclodeca-4-ene-2,6-diyn-1-one；3,4-Benzocyclodec-3-ene-1,5-diyn-7-one；7-oxo-benzo[c]cyclodeca-1,5-diyne；benzo[4,5]cyclodec-4-ene-2,6-diyn-1-one；5,6,11,12-tetradehydro-9,10-dihydro-8H-benzo[10]annulen-7-one
• CAS: 146978-90-7
• 化学式: C₁₄H₁₀O
• 分子量: 194.233
• InChiKey: FVQOPAYENAGBGY-UHFFFAOYSA-N

物化性质

• 沸点：
  371.2±22.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  benzo<4,5>cyclodec-4-ene-2,6-diyn-1-one 在 1,4-环己二烯 作用下， 以 氘代苯 为溶剂， 以75%的产率得到3,4-dihydro-1(2H)-anthracenone
  参考文献：
  名称：

  Arene 1,4-Diradical Formation from o-Dialkynylarenes

  摘要：

  A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l,l-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 degrees C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 degrees C.

  DOI：

  10.1021/jo00096a057
• 作为产物：
  描述：

  2-(2-乙炔基苯基)乙炔基三甲基硅烷 在 2,6-二甲基吡啶 、 六甲基磷酰三胺 、 正丁基锂 、 barium permanganate 、 四丁基氟化铵 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 丙酮 为溶剂， 反应 82.5h， 生成 benzo<4,5>cyclodec-4-ene-2,6-diyn-1-one
  参考文献：
  名称：

  Arene 1,4-Diradical Formation from o-Dialkynylarenes

  摘要：

  A series of 10-membered cyclic 1,5-diynes has been prepared with arene rings fused at positions C-3/C-4. The arenes include simple benzene rings, a naphthoquinone and naphthohydroquinone, and an anthraquinone and anthracene unit. Consistent with a simple picture relating the extent of double bond character in the ene part of the ene-diyne with the rate of arene-l,l-diyl formation, the hydroquinone derivatives were much less reactive compared to the corresponding quinones. Substituents such as propargylic hydroxyl or keto group have a small but significant activating effect. The parent 3,4-benzo-1,8-decadiyne shows a half-life for rearrangement of 24 h at 84 degrees C while the corresponding alkene, cyclodec-3-ene-1,5-diyne is reported to have a half-life of 18 h at 37 degrees C.

  DOI：

  10.1021/jo00096a057

文献信息

• Nouveaux dérivés de 1,5-diyne-3-cycloalcène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：ADIR ET COMPAGNIE

  公开号：EP0518753A1

  公开（公告）日：1992-12-16

  Composés de formule (I) : dans laquelle :    R représente un atome d'hydrogène, un radical acyl (C₁-C₆) linéaire ou ramifié ou un radical glycoside,    n est égal à 1 ou 2,    R₁ et R₂ représentent simultanément deux atomes d'hydrogène ou forment avec la double liaison à laquelle ils sont attachés un noyau phényle,    Médicaments.

  式(I)化合物： 其中： R 代表氢原子、直链或支链酰基（C₁-C₆）或糖苷基、 n 等于 1 或 2、 R₁ 和 R₂ 同时代表两个氢原子，或与所连接的双键一起形成一个苯基环、 药物。
• (1R)-4,5-Benzocyclodeca-4-ene-2,6-diyn-1-yl 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranoside and 4,5-Benzocyclodeca-4-ene-2,6-diyn-1-one
  作者：A. Cousson、I. Dancy、J. M. Beau

  DOI：10.1107/s0108270194008048

  日期：1995.4.15

  The title compounds, C28H30O10 and C14H10O, have been synthesized during the course of a program designed to prepare molecules with DNA-cleaving properties. The geometry of the strained benzodiyne system has been determined, the S configuration at the propargylic center established and the orientation of the sugar unit in relation to the aglycon defined. The results are compared with those for other derivatives, The molecular packing is governed by normal van der Waals interactions.
• CDPI3-enediyne and CDPI3-EDTA conjugates: a new class of DNA cleaving agents
  作者：Dale L. Boger、Jiacheng Zhou

  DOI：10.1021/jo00063a019

  日期：1993.5

  The synthesis and preliminary evaluation of la and lb, prototypical CDPI3-enediyne and CDPI3-EDTA conjugates constituting a new class of DNA cleaving agents, are detailed.
• Semmelhack M. F., Neu Thomas, Foubelo Francisco, J. Org. Chem., 59 (1994) N 17, S 5038- 5047
  作者：Semmelhack M. F., Neu Thomas, Foubelo Francisco

  DOI：——

  日期：——
• US5405948A
  申请人：——

  公开号：US5405948A

  公开（公告）日：1995-04-11