1,3-Dihydro-N,N,1,1-tetramethyl-6-isobenzofuranamin | 149331-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 1,3-Dihydro-N,N,1,1-tetramethyl-6-isobenzofuranamin
• 英文别名: N,N,3,3-tetramethyl-1H-2-benzofuran-5-amine
• CAS: 149331-25-9
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: ZKEFYAWICWDYBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-Dihydro-N,N,1,1-tetramethyl-6-isobenzofuranamin 在 正丁基锂 、 溴 作用下， 以 甲醇 为溶剂， 反应 0.84h， 生成 1,3-dihydro-1,1-dimethyl-6-dimethylamino-α-ethyl-5-isobenzofuranmethanol
  参考文献：
  名称：

  Synthesis of Isobenzofuran Derivatives as heterocyclic analogues of the herbicidesindone B

  摘要：

  The target compounds 21-27 were synthesized via bromination of the N,N,1,1-tetramethylisobenzofuranamines 13, 15 and 16, subsequent bromine-lithium exchange and reaction with propanal or propanoyl chloride, respectively. In the course of some model reactions undertaken to test a synthetic strategy based on directed ortho-lithiation governed by the dimethylamino-group a useful synthesis of the ketone 3 was developed.

  DOI：

  10.1002/prac.19943360411
• 作为产物：
  描述：

  2-(5-Dimethylamino-2-hydroxymethyl-phenyl)-propan-2-ol 在 硫酸 作用下， 反应 4.0h， 生成 1,3-Dihydro-N,N,1,1-tetramethyl-6-isobenzofuranamin
  参考文献：
  名称：

  Synthese neuer N, N,1,1-Tetramethyl-isobenzofuranamine

  摘要：

  The nitrophthalides 3 a - d aimed as intermediates in the synthesis of the title compounds 6 a - d were obtained via regioselective reduction of 3-nitro-phthalic anhydride 1 or by nitration of phthalide and 3,3-dimethylphthalide, respectively. Reductive methylation of the nitro groups afforded the dimethylaminophthalides 5 a - d which in turn were reacted with MeMgI or in the case of 5 d reduced by LiAlH4 leading finally to the title compounds.

  DOI：

  10.1002/prac.19933350104