4-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene | 32989-62-1

• 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: 4-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
• 英文别名: trans-β-(dimethylamino)-5-methoxy-2-nitrostyrene；trans-β-dimethylamino-5-methoxy-2-nitrostyrene；(E)-2-(5-methoxy-2-nitrophenyl)-N,N-dimethylethenamine
• CAS: 32989-62-1
• 化学式: C₁₁H₁₄N₂O₃
• 分子量: 222.244
• InChiKey: UXXFAOADJACLLR-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.3
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene 在 钯 作用下， 以 苯 为溶剂， 生成 5-甲氧基吲哚
  参考文献：
  名称：

  Intermediates for indoles

  摘要：

  邻硝基甲苯与甲酰胺缩醛反应，生成相应的邻硝基-β-氨基苯乙烯，经还原后发生环化反应生成吲哚。

  公开号：

  US03976639A1
• 作为产物：
  描述：

  4-硝基间甲苯酚 在 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 22.25h， 生成 4-methoxy-trans-2-[β-(dimethylamino)vinyl]-nitrobenzene
  参考文献：
  名称：

  A versatile and efficient construction of the 6H-pyrido[4,3-b]carbazole ring system. Syntheses of the antitumor alkaloids ellipticine, 9-methoxyellipticine, and olivacine, and their analogs

  摘要：

  A general and efficient synthesis of the 6H-pyrido[4,3-b]carbazole ring system is described, in which the key steps are (1) regioselective acylation of a 2-lithio-1-(phenylsulfonyl)indole (14) with 3,4-pyridinedicarboxylic acid anhydride (10), (2) cyclization of the deprotected keto acid 17 to keto lactam 19 with acetic anhydride, and (3) the addition of methyllithium to give, after reduction of the intermediate diol 23 with sodium borohydride, the target ring system. In this fashion, ellipticine (1a), 9-methoxyellipticine (1b), and 9-hydroxyellipticine (1c) were synthesized in excellent overall yields from indole. The use of Superhydride, in place of 1 equiv of methyllithium, provided a synthesis of olivacine (2), and the use of phthalic anhydride in the sequence allowed for the preparation of 6,11-dimethylbenzo[b]carbazole (48). The overall yields of ellipticine (1a) (54%) and 9-methoxyellipticine (1b) (47%) in six steps from their respective indoles represent one of the most efficient syntheses of these antitumor alkaloids.

  DOI：

  10.1021/jo00048a022

文献信息

• Microwave assisted Leimgruber–Batcho reaction for the preparation of indoles, azaindoles and pyrroylquinolines
  作者：Jason Siu、Ian R. Baxendale、Steven V. Ley

  DOI：10.1039/b313012f

  日期：——

  catalysed Leimgruber-Batcho indole synthesis using microwave acceleration is described. This approach has permitted the preparation of a variety of heteroaromatic enamine intermediates in good yield and high purities. Subsequent catalytic hydrogenation reactions, under various conditions including the use of a solid-phase encapsulated catalyst, furnish the corresponding indole derivatives in good yields

  描述了开发利用微波加速的路易斯酸催化的Leimgruber-Batcho吲哚合成的增强条件。该方法允许以高收率和高纯度制备各种杂芳族烯胺中间体。随后的催化氢化反应，在各种条件下，包括使用固相包封的催化剂，以良好的收率提供了相应的吲哚衍生物。
• PROCESS FOR THE PREPARATION OF 6-SUBSTITUTED-1-(2H)-ISOQUINOLINONES
  申请人：ROSSEN Kai

  公开号：US20110021779A1

  公开（公告）日：2011-01-27

  The present invention relates to a process for making 6-substituted-1-(2H)-isoquinolinone derivatives of formula (I) wherein R1 and n are as described in the specification. The present invention further relates to novel intermediates which are used in the process according to the invention and to processes for preparing such intermediates.

  本发明涉及一种制备式（I）中R1和n如规范所述的6-取代-1-(2H)-异喹啉酮衍生物的方法。本发明还涉及用于该发明方法的新型中间体以及制备这种中间体的方法。
• US3976639A
  申请人：——

  公开号：US3976639A

  公开（公告）日：1976-08-24