tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate | 474397-69-8

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate
• 英文别名: tert-butyl (6aR,9R,10aR)-9-[3-(dimethylamino)propyl-(ethylcarbamoyl)carbamoyl]-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-4-carboxylate
• CAS: 474397-69-8
• 化学式: C₃₁H₄₅N₅O₄
• 分子量: 551.729
• InChiKey: RNPQKJKTJYGSBO-QIGHUWCUSA-N

物化性质

• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  40
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate 在 盐酸 作用下， 以 水 为溶剂， 反应 1.0h， 生成 卡麦角林
  参考文献：
  名称：

  A Practical Synthesis of Cabergoline

  摘要：

  Cabergoline is an N-acylurea derived from 9,10-dihydrolysergic acid, which is a potent prolactin inhibitor. It is marketed by Pharmacia as Dostinex for the treatment of hyperprolactinemia and is currently under active development for the treatment of a variety of CNS disorders. In the existing process, the N-acylurea is formed by the reaction of an amide with a large excess of ethyl isocyanate at elevated temperatures. An improved process was developed that eliminates this hazardous reaction. The amide is reacted with phenyl chloroformate and then with ethylamine, which provides a mild and efficient means of forming the unsymmetrical N-acylurea.

  DOI：

  10.1021/jo0203847
• 作为产物：
  描述：

  tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl]amino]carbonyl]ergoline-1-carboxylate 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 18.0h， 生成 tert-butyl (5R,8R,10R)-6-allyl-8-[[[3-(dimethylamino)propyl][(ethylamino)carbonyl]amino]carbonyl]ergoline-1-carboxylate
  参考文献：
  名称：

  A Practical Synthesis of Cabergoline

  摘要：

  Cabergoline is an N-acylurea derived from 9,10-dihydrolysergic acid, which is a potent prolactin inhibitor. It is marketed by Pharmacia as Dostinex for the treatment of hyperprolactinemia and is currently under active development for the treatment of a variety of CNS disorders. In the existing process, the N-acylurea is formed by the reaction of an amide with a large excess of ethyl isocyanate at elevated temperatures. An improved process was developed that eliminates this hazardous reaction. The amide is reacted with phenyl chloroformate and then with ethylamine, which provides a mild and efficient means of forming the unsymmetrical N-acylurea.

  DOI：

  10.1021/jo0203847

文献信息

• New and efficient process for the preperation of cabergoline and its intermediates
  申请人：Wang Zhi-Xian

  公开号：US20080275240A1

  公开（公告）日：2008-11-06

  This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.

  这项发明涉及一种用于生产多巴胺激动剂（如卡贝哌酮）及其中间体的新型高效工艺。
• Process for the Preparation of Cabergoline
  申请人：Galambos Janos

  公开号：US20070293677A1

  公开（公告）日：2007-12-20

  A process for preparing cabergoline (I) from ergoline-8β-carboxylic acid ester (XIII) comprising the following steps. (XIII), (XVI), (XVII), (XVIII), (XIX), (I). The present case also relates to the intermediates (XVI), (XVII), (XVIII) and (XIX) as well as the polymorphic amorphous form of Cabergoline (I) and the production thereof.

  一种从麦角酸8β-羧酸酯（XIII）制备卡贝肯（I）的工艺，包括以下步骤：（XIII），（XVI），（XVII），（XVIII），（XIX），（I）。本案还涉及中间体（XVI），（XVII），（XVIII）和（XIX），以及卡贝肯（I）的多晶无定形形式及其生产。
• J. Org. Chem. 2002, 67, 7147-7150
  作者：

  DOI：——

  日期：——
• US7858791B2
  申请人：——

  公开号：US7858791B2

  公开（公告）日：2010-12-28
• US7939665B2
  申请人：——

  公开号：US7939665B2

  公开（公告）日：2011-05-10