N-Methoxy-N-methyl-2-(3-methyl-furan-2-ylmethoxy)-acetamide | 908238-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: N-Methoxy-N-methyl-2-(3-methyl-furan-2-ylmethoxy)-acetamide
• 英文别名: N-methoxy-N-methyl-2-[(3-methylfuran-2-yl)methoxy]acetamide
• CAS: 908238-76-6
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: HQIMMORIIKXMPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Methoxy-N-methyl-2-(3-methyl-furan-2-ylmethoxy)-acetamide 在 氨 、 lithium diisopropyl amide 作用下， 以 甲苯 为溶剂， 生成 (1S,5S,9R,10R,14R)-9-methyl-14-propan-2-yl-3,6-dioxa-17-azapentacyclo[8.7.0.01,5.05,9.011,15]heptadeca-7,11(15)-dien-16-one
  参考文献：
  名称：

  Novel Reaction Pathways for 2-Pyridone [4+4] Photoadducts

  摘要：

  Transannular ring closure of a pyridone-furan [4+4] photoadduct has been evaluated in a model system. A combination of nitrogen substitution and an isopropyl group gave full control of the four new stereogenic centers. Chlorination transformed the 1,5-cyclooctadiene to a [4.2.0] ring system instead of to the expected [3.3.0] ring system. Changing an alkene to an enone suppressed this pathway and led to a new rearrangement, converting the 5-8-5 ring system to a 6-7-5 system.

  DOI：

  10.1021/ol061266z
• 作为产物：
  描述：

  (3-甲基-2-呋喃基)甲醇 、 2-氯-正甲氧基-正甲基乙酰胺 在 sodium hydride 作用下， 以36%的产率得到N-Methoxy-N-methyl-2-(3-methyl-furan-2-ylmethoxy)-acetamide
  参考文献：
  名称：

  Novel Reaction Pathways for 2-Pyridone [4+4] Photoadducts

  摘要：

  Transannular ring closure of a pyridone-furan [4+4] photoadduct has been evaluated in a model system. A combination of nitrogen substitution and an isopropyl group gave full control of the four new stereogenic centers. Chlorination transformed the 1,5-cyclooctadiene to a [4.2.0] ring system instead of to the expected [3.3.0] ring system. Changing an alkene to an enone suppressed this pathway and led to a new rearrangement, converting the 5-8-5 ring system to a 6-7-5 system.

  DOI：

  10.1021/ol061266z

文献信息

• Tetraquinanes via [4 + 4] Photocycloaddition/Transannular Ring Closure
  作者：Peiling Chen、Patrick J. Carroll、Scott McN. Sieburth

  DOI：10.1021/ol101802s

  日期：2010.10.15

  Intramolecular [4 + 4] photocycloaddition of a furan and a cyclopentane-annulated 2-pyridone yields a cyclooctadiene product with four new stereogenic centers. Transannular ring closure produces the 5−5−5−5 fused ring system of the crinipellins, including three contiguous quaternary carbons, with the correct absolute stereochemistry derived from (−)-carvone.

  呋喃和环戊烷环化的2-吡啶酮的分子内[4 + 4]光环加成产生具有四个新的立体生成中心的环辛二烯产物。跨瓣环闭合产生了crinipellins的5-5-5-5稠合环系统，包括三个连续的季碳，具有正确的绝对立体化学，其衍生自（-）-香芹酮。