1,4-Dimethoxy-2,3-bis-trimethylsilanylethynyl-naphthalene | 157528-07-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Dimethoxy-2,3-bis-trimethylsilanylethynyl-naphthalene
• CAS: 157528-07-9
• 化学式: C₂₂H₂₈O₂Si₂
• 分子量: 380.634
• InChiKey: LQZWBHVRSKSZTL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,4-Dimethoxy-2,3-bis-trimethylsilanylethynyl-naphthalene 在 potassium fluoride 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 水 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 53.5h， 生成 1,4-Dihydro-1,4-dioxonaphtho<3,4-b>cyclodec-3-ene-1,5-diyne
  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：

  2,3-二溴-1,4-萘醌 在 copper(l) iodide 、 四(三苯基膦)钯 哌啶 、 sodium dithionite 、 sodium hydride 作用下， 反应 15.0h， 生成 1,4-Dimethoxy-2,3-bis-trimethylsilanylethynyl-naphthalene
  参考文献：
  名称：

  Arene 1,4-diradical formation from o-dialkynylarenes

  摘要：

  A series of five arene and quinone derivatives with dialkynyl substituents in the ortho positions and fixed in a 10-membered ring were prepared and tested with respect to thermal rearrangement to the corresponding arene 1,4 diradicals.

  DOI：

  10.1016/s0040-4039(00)92066-5

文献信息

• Synthesis and properties of 1,4-dimethoxynaphtho[2,3]-annelated dehydroannulenes
  作者：Tohru Nishinaga、Hideaki Nakayama、Nobutake Nodera、Koichi Komatsu

  DOI：10.1016/s0040-4039(98)01517-2

  日期：1998.9

  Synthesis and characterization of dehydroannulenes which consist of 1,4-dimethoxynaphthalene units connected at the 2,3-positions by acetylene and butadiyne linkages are described. The H-1 NMR spectra indicated neither significant diatropicity nor paratropicity in all of these annulenes. The electronic absorption maximum of the planar annulenes was shifted bathochromically compared with the absorption of 1,4-dimethoxy-2,3-bis[(trimethylsilyl)ethynyl)]naphthalene as a reference, whereas not much bathochromic shift was observed for annulenes with non-planar pi-systems. (C) 1998 Elsevier Science Ltd. All rights reserved.