di-tert-butyl 2-tert-butylamino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3,4-dicarboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: di-tert-butyl 2-tert-butylamino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3,4-dicarboxylate
• 英文别名: Di-t-butyl 2-t-butylamino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4h-chromene-3,4-dicarboxylate；ditert-butyl 2-(tert-butylamino)-7,7-dimethyl-5-oxo-6,8-dihydro-4H-chromene-3,4-dicarboxylate
• 化学式: C₂₅H₃₉NO₆
• 分子量: 449.588
• InChiKey: AEOGBUXPXLKKFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  异氰酸叔丁酯 、 丁炔二酸二叔丁酯 乙炔二羧酸二叔丁酯 、 5,5-二甲基-1,3-环己二酮 以 氯仿 为溶剂， 反应 24.0h， 以98%的产率得到di-tert-butyl 2-tert-butylamino-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3,4-dicarboxylate
  参考文献：
  名称：

  Reaction Between Alkyl Isocyanides and Cyclic 1,3-Diketones: A Convenient Synthesis of Functionalized 4 H -Pyrans

  摘要：

  Alkyl isocyanides react with dialkyl acetylendicarboxylates in the presence of CH-acids such as cyclopentane-1,3-dione, cyclohexane-1,3-dione, or 5,5-dimethylcyclohexane-1,3-dione to afford highly functionalized 4H-pyrans in fairly high yields. In the case of reaction between dimethyl acetylenedicarboxylate and 5,5-dimethylcyclohexane-1,3-dione in the presence of cyclohexyl isocyanide or benzyl isocyanide tetrahydro-cyclopenta[b]pyran derivatives were isolated in addition to the 4H-pyran system. The free energy barrier (96.9 kJ mol(-1)) for restricted rotation around the polarized double bond of the enaminone moiety in dimethyl 2-[cyclohexylamino-(4,4-dimethyl-2,6-dioxocyclohexylidene)methyl]but-2-enedioate was determined by dynamic NMR spectroscopy.

  DOI：

  10.1007/s00706-003-0062-9

文献信息

• Reaction Between Alkyl Isocyanides and Cyclic 1,3-Diketones: A Convenient Synthesis of Functionalized 4 H -Pyrans
  作者：Malek T. Maghsoodlou、Issa Yavari、Farough Nassiri、Hoorieh Djahaniani、Zahra Razmjoo

  DOI：10.1007/s00706-003-0062-9

  日期：2003.12.1

  Alkyl isocyanides react with dialkyl acetylendicarboxylates in the presence of CH-acids such as cyclopentane-1,3-dione, cyclohexane-1,3-dione, or 5,5-dimethylcyclohexane-1,3-dione to afford highly functionalized 4H-pyrans in fairly high yields. In the case of reaction between dimethyl acetylenedicarboxylate and 5,5-dimethylcyclohexane-1,3-dione in the presence of cyclohexyl isocyanide or benzyl isocyanide tetrahydro-cyclopenta[b]pyran derivatives were isolated in addition to the 4H-pyran system. The free energy barrier (96.9 kJ mol(-1)) for restricted rotation around the polarized double bond of the enaminone moiety in dimethyl 2-[cyclohexylamino-(4,4-dimethyl-2,6-dioxocyclohexylidene)methyl]but-2-enedioate was determined by dynamic NMR spectroscopy.