tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]-benzazepine-5-spiro-cyclohexa-2',5'-diene-2-carboxylate | 180200-06-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]-benzazepine-5-spiro-cyclohexa-2',5'-diene-2-carboxylate
• 英文别名: tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]benzazepine-5-spiro-1'-cyclohexa-2',5'-diene-2-carboxylate；tert-butyl 7,8-dimethoxy-6'-oxospiro[3,4-dihydro-1H-2-benzazepine-5,3'-cyclohexa-1,4-diene]-2-carboxylate
• CAS: 180200-06-0
• 化学式: C₂₂H₂₇NO₅
• 分子量: 385.46
• InChiKey: DJFMMRZYDCLOPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]-benzazepine-5-spiro-cyclohexa-2',5'-diene-2-carboxylate 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 以100%的产率得到7,8-dimethoxy-2,3,4,5-tetrahydro-1H-[2]benzazepinium-5-spiro-1'-cyclohexa-2',5'-dien-4'-one chloride
  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：

  tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]-benzazepine-5-spiro-1'-cyclohex-2'-ene-2-carboxylate 在 selenium(IV) oxide 、 溶剂黄146 作用下， 以 叔丁醇 为溶剂， 反应 48.0h， 以73%的产率得到tert-butyl 7,8-dimethoxy-4'-oxo-2,3,4,5-tetrahydro-1H-[2]-benzazepine-5-spiro-cyclohexa-2',5'-diene-2-carboxylate
  参考文献：
  名称：

  Concise Total Synthesis of (±)-Maritidine

  摘要：

  Maritidine can be readily obtained from the corresponding protected beta, gamma-unsaturated ketone. The quaternary carbon of maritidine was created for the first time via an intramolecular Heck reaction.

  DOI：

  10.1021/ol0343358

文献信息

• A New H₂O₂/Acid Anhydride System for the Iodoarene-Catalyzed C−C Bond-Forming Reactions of Phenols
  作者：Toshifumi Dohi、Yutaka Minamitsuji、Akinobu Maruyama、Satoshi Hirose、Yasuyuki Kita

  DOI：10.1021/ol801321f

  日期：2008.8.21

  We have succeeded in the first versatile iodoarene-catalyzed C-C bond-forming reactions by development of a new reoxidation system at low temperatures using stoichiometric bis(trifluoroacetyl) peroxide A in 2,2,2-trifluoroethanol (TFE). The catalytic system supplies a wide range of substrates and functional availabilities sufficient to be used in the key synthetic process of producing biologically important Amaryllidaceae alkaloids.
• Concise Total Synthesis of (±)-Maritidine
  作者：Claire Bru、Claude Thal、Catherine Guillou

  DOI：10.1021/ol0343358

  日期：2003.5.1

  Maritidine can be readily obtained from the corresponding protected beta, gamma-unsaturated ketone. The quaternary carbon of maritidine was created for the first time via an intramolecular Heck reaction.
• 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.