| 1610423-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1610423-74-9
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: DGXFSVLKZSASCF-UHFFFAOYSA-N

物化性质

• 沸点：
  356.1±31.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 sodium hydroxide 、 四溴化碳 、 三苯基膦 作用下， 以 甲醇 为溶剂， 以46%的产率得到3-(2-bromoethyl)chroman-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
• 作为产物：
  描述：

  C₁₃H₁₄O₄ 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 24.0h， 以26%的产率得到
  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