2,3-dihydro-1-hydroxy-1-(3,3-dimethyl-1-butynyl)-1H-phenalene | 225091-06-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,3-dihydro-1-hydroxy-1-(3,3-dimethyl-1-butynyl)-1H-phenalene
• 英文别名: 1-(3,3-Dimethylbut-1-ynyl)-2,3-dihydrophenalen-1-ol
• CAS: 225091-06-5
• 化学式: C₁₉H₂₀O
• 分子量: 264.367
• InChiKey: HOMYXEXXICDQGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 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：

  2,3-dihydro-1-hydroxy-1-(3,3-dimethyl-1-butynyl)-1H-phenalene 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 3-(3,3-Dimethyl-but-1-ynyl)-1H-phenalene
  参考文献：
  名称：

  Substituent-induced polarization of charge in phenalenyl anions

  摘要：

  The effect of trimethylsilyl, alkynyl and cyano substituents on the charge distribution of the phenalenyl anionic nucleus was examined using semiempirical calculations and NMR spectroscopy. With these techniques it was demonstrated that the trimethylsilyl and cyano substituents are capable of attracting adjacent negative charge. Examples of reactions from the literature confirm the charge-attracting capabilities of the trimethylsilyl substituent. The alkynyl substituent was shown to perturb the charge distribution of the phenalenyl moiety to a much lesser degree than the vinyl substituent in the 1-hydropyrenyl anion. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<86::aid-poc98>3.0.co;2-c
• 作为产物：
  描述：

  3,3-二甲基-1-丁炔 、 2,3-二氢-1H-苯并-1-酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到2,3-dihydro-1-hydroxy-1-(3,3-dimethyl-1-butynyl)-1H-phenalene
  参考文献：
  名称：

  Substituent-induced polarization of charge in phenalenyl anions

  摘要：

  The effect of trimethylsilyl, alkynyl and cyano substituents on the charge distribution of the phenalenyl anionic nucleus was examined using semiempirical calculations and NMR spectroscopy. With these techniques it was demonstrated that the trimethylsilyl and cyano substituents are capable of attracting adjacent negative charge. Examples of reactions from the literature confirm the charge-attracting capabilities of the trimethylsilyl substituent. The alkynyl substituent was shown to perturb the charge distribution of the phenalenyl moiety to a much lesser degree than the vinyl substituent in the 1-hydropyrenyl anion. Copyright (C) 1999 John Wiley & Sons, Ltd.

  DOI：

  10.1002/(sici)1099-1395(199902)12:2<86::aid-poc98>3.0.co;2-c