2-(trimethylsilyl)ethyl 1-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)-2-azabutane-2-carboxylate

• 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: 2-(trimethylsilyl)ethyl 1-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)-2-azabutane-2-carboxylate
• 英文别名: 2-trimethylsilylethyl N-[(3,4-dimethoxyphenyl)methyl]-N-[2-(4-hydroxyphenyl)ethyl]carbamate
• 化学式: C₂₃H₃₃NO₅Si
• 分子量: 431.604
• InChiKey: MILWINMGSJZJEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.93
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 1-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)-2-azabutane-2-carboxylate 在 [双(三氟乙酰氧基)碘]苯 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.08h， 以54%的产率得到2-(trimethylsilyl)ethyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-diene-2-carboxylate
  参考文献：
  名称：

  An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent

  摘要：

  The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p' coupling (11) and p-o' coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3' position (10) with PIFA.

  DOI：

  10.1021/jo9606766
• 作为产物：
  描述：

  4-(2-(3,4-二甲氧基苄基氨基)乙基)苯酚 、 对硝基苯基三甲基硅乙基碳酸酯 在 碳酸氢钠 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 12.0h， 以78%的产率得到2-(trimethylsilyl)ethyl 1-(3,4-dimethoxyphenyl)-4-(4-hydroxyphenyl)-2-azabutane-2-carboxylate
  参考文献：
  名称：

  An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent

  摘要：

  The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p' coupling (11) and p-o' coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3' position (10) with PIFA.

  DOI：

  10.1021/jo9606766

文献信息

• An Oxidative Intramolecular Phenolic Coupling Reaction for the Synthesis of Amaryllidaceae Alkaloids Using a Hypervalent Iodine(III) Reagent
  作者：Yasuyuki Kita、Takeshi Takada、Michiyo Gyoten、Hirofumi Tohma、Meinhart H. Zenk、Jörg Eichhorn

  DOI：10.1021/jo9606766

  日期：1996.1.1

  The oxidative intramolecular phenolic coupling reaction of norbelladine derivatives (1) was investigated with the aim of preparing amaryllidaceae alkaloids. Spirodienone compounds (2), which are intermediates for the synthesis of an amaryllidaceae alkaloid, (+)-maritidine, or phenol ether derivatives containing the 5,6,7,8-tetrahydrobenzazocine systems (9), were selectively obtained by the reaction of 1 and the hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA). Both p-p' coupling (11) and p-o' coupling spirodienone compounds (12) were obtained by the reaction of phenol derivatives having an alkoxy group at the C-3' position (10) with PIFA.