2,2-Dimethyl-6-trimethylsilyl-1,3-benzodioxole-5-carbaldehyde | 213984-60-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2,2-Dimethyl-6-trimethylsilyl-1,3-benzodioxole-5-carbaldehyde
• CAS: 213984-60-2
• 化学式: C₁₃H₁₈O₃Si
• 分子量: 250.37
• InChiKey: LLHBALUGEXCBDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2-Dimethyl-6-trimethylsilyl-1,3-benzodioxole-5-carbaldehyde 在 sodium tetrahydroborate 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 吡啶 为溶剂， 反应 6.5h， 生成 2,2-dimethyl-7-(2,2,2-trifluoroacetyl)-5-trimethylsilylspiro[8,9-dihydro-6H-[1,3]dioxolo[4,5-g][2]benzazepine-10,4'-cyclohexa-2,5-diene]-1'-one
  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 manganese(IV) oxide 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 硫酸 、 sodium methylate 、 phosphorus pentoxide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 28.5h， 生成 2,2-Dimethyl-6-trimethylsilyl-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

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.