ethyl cis-6-aza-2-[(tert-butoxy)carbonylamino]-7-(4-bromophenyl)-5-oxaspiro[3.4]oct-6-ene-2-carboxylate | 281207-63-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl cis-6-aza-2-[(tert-butoxy)carbonylamino]-7-(4-bromophenyl)-5-oxaspiro[3.4]oct-6-ene-2-carboxylate
• CAS: 281207-63-4
• 化学式: C₂₀H₂₅BrN₂O₅
• 分子量: 453.333
• InChiKey: HJMAXBFYTRRBIP-BGYRXZFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  86.22
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl cis-6-aza-2-[(tert-butoxy)carbonylamino]-7-(4-bromophenyl)-5-oxaspiro[3.4]oct-6-ene-2-carboxylate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl cis-6-aza-7-(4-bromophenyl)-5-oxa-2[(phenylamino)carbonylamino]spiro[3.4]oct-6-ene-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of Hydantoin- and Isoxazoline-Substituted Dispirocyclobutanoids

  摘要：

  Synthetic strategies for constructing novel achiral cyclobutanoid isoxazolidinoimidazolidinedione heterocycles, with a generalized structure of II, have been developed via 1,3-dipolar cycloaddition and carbanilide cyclization transformations from methylenecyclobutane 13. The exo methylene cyclobutane system has made the realization of some diasteroselectivity possible, such that the H-bond (Boc-NH) directed product (i.e., 14) was obtained with 3:1 selectivity relative to the non-H-bond directed product (i.e., 15).

  DOI：

  10.1021/jo000152c
• 作为产物：
  描述：

  4-bromobenzaldehyde oxime 、 ethyl 1-[(tert-butoxy)carbonylamino]-3-methylenecyclobutanecarboxylate 在 sodium hypochlorite 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以35%的产率得到ethyl cis-6-aza-2-[(tert-butoxy)carbonylamino]-7-(4-bromophenyl)-5-oxaspiro[3.4]oct-6-ene-2-carboxylate
  参考文献：
  名称：

  Diastereoselective Synthesis of Hydantoin- and Isoxazoline-Substituted Dispirocyclobutanoids

  摘要：

  Synthetic strategies for constructing novel achiral cyclobutanoid isoxazolidinoimidazolidinedione heterocycles, with a generalized structure of II, have been developed via 1,3-dipolar cycloaddition and carbanilide cyclization transformations from methylenecyclobutane 13. The exo methylene cyclobutane system has made the realization of some diasteroselectivity possible, such that the H-bond (Boc-NH) directed product (i.e., 14) was obtained with 3:1 selectivity relative to the non-H-bond directed product (i.e., 15).

  DOI：

  10.1021/jo000152c