spiro[chromane-3,1’-cyclopropan]-4-one | 1368407-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: spiro[chromane-3,1’-cyclopropan]-4-one
• 英文别名: 2,4-Dihydrospiro[1-benzopyran-3,1'-cyclopropane]-4-one；spiro[2H-chromene-3,1'-cyclopropane]-4-one
• CAS: 1368407-47-9
• 化学式: C₁₁H₁₀O₂
• 分子量: 174.199
• InChiKey: VIYPIHVEAISRIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  spiro[chromane-3,1’-cyclopropan]-4-one 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 氯化亚砜 、 盐酸羟胺 、 potassium carbonate 、 三氯氧磷 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 38.0h， 生成 5-(6-(difluoromethyl)-5-methylpyridin-3-yl)-2H-spiro[benzo[f][1,4]oxazepine-3,1’-cyclopropane]
  参考文献：
  名称：

  NEW SUBSTITUTED TETRAHYDROBENZOXAZEPINE

  摘要：

  The present invention relates to the compounds of formula (I) wherein the variables are defined as given in the description and claims. The invention further relates to their use and composition.

  公开号：

  WO2024104823A1
• 作为产物：
  描述：

  3-(2-bromoethyl)chroman-4-one 在 3-mesityl-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazol-3-ium perchlorate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以92%的产率得到spiro[chromane-3,1’-cyclopropan]-4-one
  参考文献：
  名称：

  N-Heterocyclic Carbene Catalyzed Intramolecular Acylation of Allylic Electrophiles

  摘要：

  The N-heterocyclic carbene (NHC) catalyzed addition reaction has been well documented recently; however, the NHC-catalyzed substitution reaction especially the S(N)2' type reaction remains a challenge. As one of the most fundamental reaction types in organic chemistry, the S(N)2' reaction catalyzed by NHC would be a powerful tool in organic synthesis. Therefore, the first NHC-catalyzed intramolecular S(N)2' substitution reaction of aldehyde with allylic electrophiles has been developed. A variety of alpha,beta-unsaturated chromanones were obtained under a domino S(N)2' reaction and isomerization. Mechanistic experiments were conducted to confirm the nature of this S(N)2' reaction.

  DOI：

  10.1021/ol501046p