N-[(2,2-diphenyl-6-triethylsilyl-1,3-benzodioxol-5-yl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide | 213984-42-0

• 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: N-[(2,2-diphenyl-6-triethylsilyl-1,3-benzodioxol-5-yl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide
• CAS: 213984-42-0
• 化学式: C₃₆H₃₈F₃NO₄Si
• 分子量: 633.783
• InChiKey: CFBMORVQCUEKAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  45
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-[(2,2-diphenyl-6-triethylsilyl-1,3-benzodioxol-5-yl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 various solvent(s) 为溶剂， 反应 1.5h， 以37%的产率得到2,2-diphenyl-5-triethylsilyl-7-(2,2,2-trifluoroacetyl)spiro[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 、 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 lithium aluminium tetrahydride 、 正丁基锂 、 硫酸 、 对甲苯磺酸 作用下， 以 吡啶 、 乙醚 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 33.84h， 生成 N-[(2,2-diphenyl-6-triethylsilyl-1,3-benzodioxol-5-yl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide
  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.