1,3-二噁烷-4,6-二酮,5-[[(1,1-二甲基乙基)氨基]亚甲基]-2,2-二甲基- | 118060-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1,3-二噁烷-4,6-二酮,5-[[(1,1-二甲基乙基)氨基]亚甲基]-2,2-二甲基-
• 英文名称: 5-(N-t-butyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-<(tert-butylamino)methylene>-1,3-dioxane-4,6-dione；5-(Dimethylethylaminomethylene)-2,2-dimethyl-1,3-dioxane-4,6-dione；5-[(tert-butylamino)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 118060-67-6
• 化学式: C₁₁H₁₇NO₄
• 分子量: 227.26
• InChiKey: IBVULAHGUPPRDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,3-二噁烷-4,6-二酮,5-[[(1,1-二甲基乙基)氨基]亚甲基]-2,2-二甲基- 在 sodium hydride 作用下， 以 二甲基亚砜 为溶剂， 25.0~600.0 ℃ 、1.33 Pa 条件下， 生成 1-叔丁基-2H-吡咯-3-酮
  参考文献：
  名称：

  3-羟基吡咯和1 H-吡咯-3（2 H）-ones 。第2部分。氨基亚甲基梅德鲁姆酸衍生物热解合成吡咯-3-酮的范围和局限性

  摘要：

  N，N-二取代的氨基亚甲基Meldrum的酸衍生物的快速真空热解通过氢转移-环化序列提供了通往4,5-未取代的1 H-吡咯-3（2 H）-ones的途径。可以获得烷基和芳基的1-取代的，1,2-二取代的和1,2,2-三取代的吡咯烷酮。在竞争性情况下，尽管苄基氢原子被证明具有特别的反应性，但从伯，仲或叔位转移的氢之间几乎没有选择性，从而可以合成2-苯基-1 H-吡咯-3（2 H）-。

  DOI：

  10.1039/p19880000863
• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 反应 14.0h， 生成 1,3-二噁烷-4,6-二酮,5-[[(1,1-二甲基乙基)氨基]亚甲基]-2,2-二甲基-
  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：——
• MCNAB, HAMISH;MONAHAN, LILIAN C., J. CHEM. SOC. PERKIN TRANS.,(1988) N 4, 863-868
  作者：MCNAB, HAMISH、MONAHAN, LILIAN C.

  DOI：——

  日期：——
• 3-Hydroxypyrroles and 1H-pyrrol-3(2H)-ones. Part 2. Scope and limitations of the synthesis of pyrrol-3-ones by pyrolysis of aminomethylene Meldrum's acid derivatives
  作者：Hamish McNab、Lilian C. Monahan

  DOI：10.1039/p19880000863

  日期：——

  Flash vacuum pyrolysis of N,N-disubstituted aminomethylene Meldrum's acid derivatives provides a route to 4,5-unsubstituted 1H-pyrrol-3(2H)-ones by a hydrogen-transfer–cyclisation sequence. Alkyl and aryl 1-substituted, 1,2-disubstituted, and 1,2,2-trisubstituted pyrrolones can be obtained. In competitive cases, there is little selectivity between hydrogen transfer from primary, secondary, or tertiary

  N，N-二取代的氨基亚甲基Meldrum的酸衍生物的快速真空热解通过氢转移-环化序列提供了通往4,5-未取代的1 H-吡咯-3（2 H）-ones的途径。可以获得烷基和芳基的1-取代的，1,2-二取代的和1,2,2-三取代的吡咯烷酮。在竞争性情况下，尽管苄基氢原子被证明具有特别的反应性，但从伯，仲或叔位转移的氢之间几乎没有选择性，从而可以合成2-苯基-1 H-吡咯-3（2 H）-。
• 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.