2,2-dimethyl-5-<2-(isopropylamino)ethylidene>-1,3-dioxane-4,6-dione | 131297-17-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-5-<2-(isopropylamino)ethylidene>-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-[1-(propan-2-ylamino)ethylidene]-1,3-dioxane-4,6-dione
• CAS: 131297-17-1
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: UOWBJUVMJXBMIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-5-<2-(isopropylamino)ethylidene>-1,3-dioxane-4,6-dione 600.0 ℃ 、133.32 Pa 条件下， 以31%的产率得到(E)-3-Isopropylideneamino-but-2-enal
  参考文献：
  名称：

  Synthesis of .alpha.-cyano carbonyl compounds by flash vacuum thermolysis of (alkylamino)methylene derivatives of Meldrum's acid. Evidence for facile 1,3-shifts of alkylamino and alkylthio groups in imidoylketene intermediates

  摘要：

  The syntheses and flash vacuum thermolyses of 5-[(alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones (Meldrum's acid derivatives) 13a-i are described. Thermolysis of 13a as well as of ethyl 3-(tert-butylamino)acrylate (22) gives a tautomeric mixture of cyanoacetaldehyde (14) and 3-hydroxypropenenitrile (15). Thermolysis of 13b gives iminoacrolein 26 and not cyanoacetone (29). Thermolysis of 13c,d gives S-methyl cyanothioacetate (30), and 13f-h give cyanoacetamides 31 in high yields. 2-Cyanopent-4-enoic acid derivatives 32 are obtained from Meldrum's acids 13e,i. The results are discussed in terms of facile 1,3-shifts of methylthio and alkylamino groups in imidoylketenes, interconverting imidoylketenes and acylketene imines.

  DOI：

  10.1021/jo00003a014
• 作为产物：
  描述：

  5-(1-methoxyethylene) Meldrum's acid 、 异丙胺 以 乙腈 为溶剂， 反应 12.0h， 以84%的产率得到2,2-dimethyl-5-<2-(isopropylamino)ethylidene>-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Synthesis of .alpha.-cyano carbonyl compounds by flash vacuum thermolysis of (alkylamino)methylene derivatives of Meldrum's acid. Evidence for facile 1,3-shifts of alkylamino and alkylthio groups in imidoylketene intermediates

  摘要：

  The syntheses and flash vacuum thermolyses of 5-[(alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones (Meldrum's acid derivatives) 13a-i are described. Thermolysis of 13a as well as of ethyl 3-(tert-butylamino)acrylate (22) gives a tautomeric mixture of cyanoacetaldehyde (14) and 3-hydroxypropenenitrile (15). Thermolysis of 13b gives iminoacrolein 26 and not cyanoacetone (29). Thermolysis of 13c,d gives S-methyl cyanothioacetate (30), and 13f-h give cyanoacetamides 31 in high yields. 2-Cyanopent-4-enoic acid derivatives 32 are obtained from Meldrum's acids 13e,i. The results are discussed in terms of facile 1,3-shifts of methylthio and alkylamino groups in imidoylketenes, interconverting imidoylketenes and acylketene imines.

  DOI：

  10.1021/jo00003a014

文献信息

• CHEIKH, ABDELHAMID;BEN;CHUCHE, JOSSELIN;MANISSE, NOEL;POMMELET, JEAN CLAU+, J. ORG. CHEM., 56,(1991) N, C. 970-975
  作者：CHEIKH, ABDELHAMID、BEN、CHUCHE, JOSSELIN、MANISSE, NOEL、POMMELET, JEAN CLAU+

  DOI：——

  日期：——
• Synthesis of .alpha.-cyano carbonyl compounds by flash vacuum thermolysis of (alkylamino)methylene derivatives of Meldrum's acid. Evidence for facile 1,3-shifts of alkylamino and alkylthio groups in imidoylketene intermediates
  作者：Abdelhamid Ben Cheikh、Josselin Chuche、Noel Manisse、Jean Claude Pommelet、Klaus Peter Netsch、Primoz Lorencak、Curt Wentrup

  DOI：10.1021/jo00003a014

  日期：1991.2

  The syntheses and flash vacuum thermolyses of 5-[(alkylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-diones (Meldrum's acid derivatives) 13a-i are described. Thermolysis of 13a as well as of ethyl 3-(tert-butylamino)acrylate (22) gives a tautomeric mixture of cyanoacetaldehyde (14) and 3-hydroxypropenenitrile (15). Thermolysis of 13b gives iminoacrolein 26 and not cyanoacetone (29). Thermolysis of 13c,d gives S-methyl cyanothioacetate (30), and 13f-h give cyanoacetamides 31 in high yields. 2-Cyanopent-4-enoic acid derivatives 32 are obtained from Meldrum's acids 13e,i. The results are discussed in terms of facile 1,3-shifts of methylthio and alkylamino groups in imidoylketenes, interconverting imidoylketenes and acylketene imines.