1-(2-isocyanophenyl)-2,2-dimethylpropan-1-ol | 1101183-61-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-isocyanophenyl)-2,2-dimethylpropan-1-ol
• 英文别名: 1-(2-Isocyanophenyl)-2,2-dimethylpropan-1-ol
• CAS: 1101183-61-2
• 化学式: C₁₂H₁₅NO
• 分子量: 189.257
• InChiKey: QJHNLEIZKOFBPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  24.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-isocyanophenyl)-2,2-dimethylpropan-1-ol 在 copper(I) oxide 作用下， 以 苯 为溶剂， 反应 1.0h， 以83%的产率得到4-tert-butyl-4H-3,1-benzoxazine
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734
• 作为产物：
  描述：

  特戊醛 、 1-溴-2-异氰基苯 在 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.33h， 以80%的产率得到1-(2-isocyanophenyl)-2,2-dimethylpropan-1-ol
  参考文献：
  名称：

  Reactions of ortho-Lithiophenyl (-Hetaryl) Isocyanides with Carbonyl Compounds: Rearrangements of 2-Metalated 4H-3,1-Benzoxazines

  摘要：

  ortho-Lithiophenyl (-hetaryl) isocyanides react with aldehydes and ketones providing isocyanoalcohols 8 (36-89%, nine examples), 4H-3,1-benzoxazines 9 (45-78%, six examples) or, after two types of rearrangements, isobenzofuran-1(3H)-imines (iminophthalanes) 18 (52-75%, four examples), or indolin-2-ones 19 (42-79%, two. examples), depending on the reaction conditions and substitution patterns. Isocyanoalcohols 8, in turn, were converted to 9 or 18 under Cu(I) catalysis (66-86%, eight examples). 4H-3, 1-Benzoxazin-4-ones 39-Nu and isatoic anhydride 40 were obtained by the reaction of 2 with carbon dioxide followed by trapping of the lithiated intermediate with iodine and subsequent reactions with nucleophiles (45-60%, three examples).

  DOI：

  10.1021/jo9004734

文献信息

• <i>ortho</i>-Lithiophenyl Isocyanide: A Versatile Precursor for 3<i>H</i>-Quinazolin-4-ones and 3<i>H</i>-Quinazolin-4-thiones
  作者：Alexander V. Lygin、Armin de Meijere

  DOI：10.1021/ol802659m

  日期：2009.1.15

  ortho-Lithiophenyl isocyanide has been generated from ortho-bromophenyl isocyanide and successfully employed toward the synthesis of 2-substituted phenyl isocyanides as well as 2,3-disubstituted 3H-quinazoline-4-ones and 3H-quinazolin-4-thiones.