Ethyl 3-(5-azabicyclo[8.4.0]tetradeca-1(14),10,12-trien-2,8-diyn-5-yl)-3-oxopropanoate | 460740-50-5

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: Ethyl 3-(5-azabicyclo[8.4.0]tetradeca-1(14),10,12-trien-2,8-diyn-5-yl)-3-oxopropanoate
• CAS: 460740-50-5
• 化学式: C₁₈H₁₇NO₃
• 分子量: 295.338
• InChiKey: LZWVUNBANXZQFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(5-azabicyclo[8.4.0]tetradeca-1(14),10,12-trien-2,8-diyn-5-yl)-3-oxopropanoate 在 dirhodium tetraacetate 对甲苯磺酰叠氮 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.67h， 生成 (4R,5S)-6-Oxo-7-aza-tricyclo[10.4.0.0^4,7]hexadeca-1(16),12,14-triene-2,10-diyne-5-carboxylic acid ethyl ester
  参考文献：
  名称：

  A carbene insertion route to β-lactam fused cyclic enediynes

  摘要：

  A new methodology has been developed for the synthesis of biologically important beta-lactam fused enediynes 1 and 2. The key step is the successful insertion of the carbene generated from the diazo enediynes 3 and 4. The result is in sharp contrast to the fate of the carbene generated from acyclic enediyne 5 in which case the rearrangement product 6 and the dimer 7 were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00724-4
• 作为产物：
  描述：

  1-[4-nitrophenylsulfonyl]-[5,6]-benz-1-aza-cyclodec-3,7-diyne 在 potassium carbonate 、 苯硫酚 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 Ethyl 3-(5-azabicyclo[8.4.0]tetradeca-1(14),10,12-trien-2,8-diyn-5-yl)-3-oxopropanoate
  参考文献：
  名称：

  A carbene insertion route to β-lactam fused cyclic enediynes

  摘要：

  A new methodology has been developed for the synthesis of biologically important beta-lactam fused enediynes 1 and 2. The key step is the successful insertion of the carbene generated from the diazo enediynes 3 and 4. The result is in sharp contrast to the fate of the carbene generated from acyclic enediyne 5 in which case the rearrangement product 6 and the dimer 7 were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00724-4

文献信息

• A carbene insertion route to β-lactam fused cyclic enediynes
  作者：Amit Basak、Subrata Mandal

  DOI：10.1016/s0040-4039(02)00724-4

  日期：2002.6

  A new methodology has been developed for the synthesis of biologically important beta-lactam fused enediynes 1 and 2. The key step is the successful insertion of the carbene generated from the diazo enediynes 3 and 4. The result is in sharp contrast to the fate of the carbene generated from acyclic enediyne 5 in which case the rearrangement product 6 and the dimer 7 were obtained. (C) 2002 Elsevier Science Ltd. All rights reserved.