carbonic acid allyl ester 6,6-dimethyl-5,7-dioxa-benzocyclohepten-9-yl ester | 925461-94-5

• 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: carbonic acid allyl ester 6,6-dimethyl-5,7-dioxa-benzocyclohepten-9-yl ester
• CAS: 925461-94-5
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: BJYPBUTZFAHPHT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  carbonic acid allyl ester 6,6-dimethyl-5,7-dioxa-benzocyclohepten-9-yl ester 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex chiral ligand 作用下， 以 1,4-二氧六环 为溶剂， 以90%的产率得到8-allyl-6,6-dimethyl-5,7-dioxa-benzocyclohepten-9-one
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a
• 作为产物：
  描述：

  2,6-dihydroxyacetophenone 在 四甲基乙二胺 、 sodium hexamethyldisilazane 、 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 carbonic acid allyl ester 6,6-dimethyl-5,7-dioxa-benzocyclohepten-9-yl ester
  参考文献：
  名称：

  Enantioselective Synthesis of α-Tertiary Hydroxyaldehydes by Palladium-Catalyzed Asymmetric Allylic Alkylation of Enolates

  摘要：

  Chiral alpha-tertiary hydroxyaldehydes are very versatile building blocks in synthetic chemistry. Herein, we report the first examples of a catalytic asymmetric protocol for the synthesis of such compounds from readily available alpha-halo or alpha-hydroxy ketones or enol silyl ethers with excellent yields and nantioselectivity. Its synthetic utility is demonstrated in the short, efficient formal synthesis of (S)-oxybutynin. In this process, the chiral ligand controls the regioselectivity as well as the enantioselectivity.

  DOI：

  10.1021/ja067342a