N-[(4,5-dimethoxy-2-trimethylsilylphenyl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide | 213984-29-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 石蒜科生物碱
• 英文名称: N-[(4,5-dimethoxy-2-trimethylsilylphenyl)methyl]-2,2,2-trifluoro-N-[2-(4-hydroxyphenyl)ethyl]acetamide
• CAS: 213984-29-3
• 化学式: C₂₂H₂₈F₃NO₄Si
• 分子量: 455.549
• InChiKey: NGVWOSPIMOPEMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.09
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 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-[(4,5-dimethoxy-2-trimethylsilylphenyl)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26%的产率得到2-(trifluoroacetyl)-7,8-dimethoxy-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-dien-4'-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：

  2-(2-bromo-4,5-dimethoxyphenyl)-1,3-dioxolane 在 sodium tetrahydroborate 、 sodium methylate 、 对甲苯磺酸 作用下， 以 吡啶 为溶剂， 反应 5.0h， 生成 N-[(4,5-dimethoxy-2-trimethylsilylphenyl)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.