(6-bromo-2,2-diphenylbenzo[1,3]dioxol-5-yl)methanol | 213984-05-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (6-bromo-2,2-diphenylbenzo[1,3]dioxol-5-yl)methanol
• 英文别名: (6-Bromo-2,2-diphenyl-1,3-benzodioxol-5-yl)methanol
• CAS: 213984-05-5
• 化学式: C₂₀H₁₅BrO₃
• 分子量: 383.241
• InChiKey: FFSPOSFVWOSZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (6-bromo-2,2-diphenylbenzo[1,3]dioxol-5-yl)methanol 在 manganese(IV) oxide 、 正丁基锂 、 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 16.17h， 生成 2,2-Diphenyl-6-triethylsilyl-1,3-benzodioxole-5-carbaldehyde
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868
• 作为产物：
  描述：

  原儿茶酸 在 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 硫酸 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.67h， 生成 (6-bromo-2,2-diphenylbenzo[1,3]dioxol-5-yl)methanol
  参考文献：
  名称：

  Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids

  摘要：

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.

  DOI：

  10.1021/jo9807868

文献信息

• Oxidative Intramolecular Phenolic Coupling Reaction Induced by a Hypervalent Iodine(III) Reagent:  Leading to Galanthamine-Type Amaryllidaceae Alkaloids
  作者：Yasuyuki Kita、Mitsuhiro Arisawa、Michiyo Gyoten、Makiko Nakajima、Ryuji Hamada、Hirofumi Tohma、Takeshi Takada

  DOI：10.1021/jo9807868

  日期：1998.9.1

  By extending our oxidative phenol-coupling reactions using a hypervalent iodine(III) reagent, a versatile synthetic procedure for the galanthamine-type Amaryllidaceae alkaloids was accomplished. The first total synthesis of (+/-)-sanguinine and the total syntheses of (+/-)-galanthamine, (+/-)-narwedine, (+/-)-lycoramine, and (+/-)-norgalanthamine were also successfully carried out.