4-hydroxy-1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacene | 1297413-58-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4-hydroxy-1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacene
• 英文别名: 1,1,7,7-Tetraethyl-3,3,5,5-tetramethyl-2,6-dihydro-s-indacen-4-ol
• CAS: 1297413-58-1
• 化学式: C₂₄H₃₈O
• 分子量: 342.565
• InChiKey: XSPGFRBQJOMCEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  395.3±42.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacene 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 十六烷基三甲基溴化铵 、 sodium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 正戊烷 为溶剂， 反应 44.5h， 生成 (3,3,5,5-Tetraethyl-8-hexoxy-1,1,7,7-tetramethyl-2,6-dihydro-s-indacen-4-yl)-[4-[(3,3,5,5-tetraethyl-8-hexoxy-1,1,7,7-tetramethyl-2,6-dihydro-s-indacen-4-yl)silyl]phenyl]silane
  参考文献：
  名称：

  Coplanar Oligo(p-phenylenedisilenylene)s as Si═Si Analogues of Oligo(p-phenylenevinylene)s: Evidence for Extended π-Conjugation through the Carbon and Silicon π-Frameworks

  摘要：

  A series of oligo(p-phenylenedisilenylene)s (Si-OPVs 1-4), silicon analogues of oligo(p-phenylenevinylene)s, up to the tetramer have been synthesized and isolated by the introduction of a newly developed protecting group [(HexO)MEind] for improving their solubility. The experimental and theoretical studies of the Si-OPVs 1-4 demonstrate the fully extended pi-conjugation of the Si-OPV main chains. Single crystal X-ray analyses of the monomer 1 and the dimer 2 revealed the highly coplanar Si-OPV backbones facilitating the effective extension of the 7r-conjugation, which has further been validated by the significant increases in the absorption maxima from 465 nm for the monomer 1 to 610 nm for the tetramer 4. The absorption maxima exhibit an excellent fit to Meier's equation, leading to the estimation of an effective conjugation length (ECL) of 9 repeat units (nEcL = 9) and the absorption maximum of 635 nm for the infinite chain (lambda(infinity) = 635 nm). In sharp contrast to other nonemissive disilenes, the Si-OPVs 2-4 show an intense fluorescence from 613 to 668 nm at room temperature with the quantum yields up to 0.48. All the data presented here provide the first evidence for the efficient extended pi-conjugation between the Si=Si double bonds and the carbon pi-electron systems over the entire Si-OPV skeleton. This study reveals the possibility for developing the conjugated disilene pi-systems, in which the Si=Si double bonds would be promising building blocks, significantly optimizing the intrinsic photophysical and electrochemical properties of the carbon-based pi-conjugated materials.

  DOI：

  10.1021/jacs.5b10113
• 作为产物：
  描述：

  4-溴-1,1,7,7-四乙基-1,2,3,5,6,7-六氢-3,3,5,5-四甲基对称引达省 在 正丁基锂 、 硝基苯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以57%的产率得到4-hydroxy-1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacene
  参考文献：
  名称：

  基于刚性稠环s - Hydrondacene骨架的大体积芳氧基配体锂和钛配合物的合成与结构表征

  摘要：

  基于刚性稠合环1,1,3,3,5,5,7,7-八角的庞大的芳基醇（Rind）OH（1）[Rind = EMind（a）和Eind（b）]通过（Rind）Li与硝基苯反应然后质子化来制备-R-取代的s-茚并茂骨架。根据所用溶剂（THF =四氢呋喃）的不同，用n BuLi处理1可获得芳基化锂二聚体[（Rind）OLi（THF）] 2（2）或三聚体[（Rind）OLi] 3（3）。[（EMind）OLi（THF）] 2（2a）与TiCl 4（THF）2的盐置换反应导致形成单核抗磁性单和双（芳氧基）Ti（IV）络合物，[（EMind）O] TiCl 3（THF）（4a）和[（EMind）O] 2 TiCl 2（5a）。我们还分离了痕量的三（芳氧基）Ti（IV）配合物，[（EMind）O] 3 TiCl（6a）。2a和TiCl 3（THF）3之间的反应导致分离出单核顺磁性单和双（芳氧基）Ti（III）配合物，[（EMind）O]

  DOI：

  10.1021/acs.inorgchem.6b00762

文献信息

• Air- and Moisture-Stable <i>p</i>-Monothiobenzoquinones Incorporated in an Octaalkyl-<i>s</i>-hydrindacene Skeleton
  作者：Makoto Hachiya、Mikinao Ito、Tsukasa Matsuo、Daisuke Hashizume、Hiroyuki Fueno、Kazuyoshi Tanaka、Kohei Tamao

  DOI：10.1021/ol200768b

  日期：2011.5.20

  p-Monothiobenzoquinones incorporated in a fused-ring octaalkyl-s-hydrindacene skeleton have been synthesized as air- and moisture-stable reddish orange, crystals by the oxidation of mercaptophenol derivatives with DDQ, which have been characterized by X-ray crystallography to show a planar quinoid framework.