(4S,4aS,8aR)-decahydro-isoquinoline-4-carboxylic acid ethyl ester | 362611-63-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (4S,4aS,8aR)-decahydro-isoquinoline-4-carboxylic acid ethyl ester
• 英文别名: (+/-)-(4s,4As,8ar)-decahydro-isoquinoline-4-carboxylic acid ethyl ester；ethyl (4S,4aS,8aR)-1,2,3,4,4a,5,6,7,8,8a-decahydroisoquinoline-4-carboxylate
• CAS: 362611-63-0
• 化学式: C₁₂H₂₁NO₂
• 分子量: 211.304
• InChiKey: TVVSTLWLDOBLBA-GARJFASQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4S,4aS,8aR)-decahydro-isoquinoline-4-carboxylic acid ethyl ester 在 lithium hydroxide 、 N,N'-羰基二咪唑 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 188.0h， 生成 demethylluvangetin
  参考文献：
  名称：

  The development of a practical synthesis of the potent and selective somatostatin sst3 receptor antagonist [4-(3,4-difluoro-phenyl)-piperazine-1-yl]-{(4S,4aS,8aR)-2[(S)-3-(6-methoxy-pyridin-3-yl)-2-methyl-propyl]-decahydroisoquinoline-4-yl}-methanone (NVP-ACQ090)

  摘要：

  The decahydroisoquinoline derivative NVP-ACQ090 is a potent and selective antagonist at the somatostatin sst(3) receptor. The original research synthesis of NVP-ACQ090 comprises a main chain of nine linear steps and two side chains of three and steps. respectively. This synthesis is highly convergent, but very complex and expensive, and involves several reagents that are not acceptable for a large scale synthesis. In chemical development. all the unacceptables could be replaced, and the overall efficiency of the synthesis was much improved. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.024
• 作为产物：
  描述：

  4-异喹啉羧酸乙酯 在 铑 甲基叔丁基醚 、 KHCO3 、 Brine 、 水 、 二氯甲烷 、 Sodium sulfate-III 、 acetate salt 作用下， 以 溶剂黄146 为溶剂， 60.0 ℃ 、1999.83 MPa 条件下， 反应 2.0h， 生成 (4S,4aS,8aR)-decahydro-isoquinoline-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Decahydro-isoquinolines

  摘要：

  本发明提供式(I)的化合物，其中A、B和R如本文所定义，并提供其制备方法。式(I)的化合物可用作生长抑素拮抗剂。

  公开号：

  US06635647B2

文献信息

• [EN] DECAHYDRO-ISOQUINOLINES<br/>[FR] DÉCAHYDRO-ISOQUINOLINES
  申请人：NOVARTIS AG

  公开号：WO2001070731A1

  公开（公告）日：2001-09-27

  The invention provides compounds of formula (I), wherein A, B and R are as defined in the description, and the preparation thereof. The compounds of formula (I) are useful as somatostatin receptor antagonists.

  本发明提供了式（I）的化合物，其中A、B和R如描述中所定义，并提供其制备方法。式（I）的化合物可用作生长抑素受体拮抗剂。
• Decahydroisoquinoline derivatives as novel non-peptidic, potent and subtype-selective somatostatin sst3 receptor antagonists
  作者：Thomas Troxler、Konstanze Hurth、Karl-Heinrich Schuh、Philippe Schoeffter、Daniel Langenegger、Albert Enz、Daniel Hoyer

  DOI：10.1016/j.bmcl.2010.01.063

  日期：2010.3

  Starting from non-peptidic sst(1)-selective somatostatin receptor antagonists, first compounds with mixed sst(1)/sst(3) affinity were identified by directed structural modifications. Systematic optimization of these initial leads afforded novel, enantiomerically pure, highly potent and sst(3)-subtype selective somatostatin antagonists based on a (4S,4aS,8aR)-decahydroisoquinoline-4-carboxylic acid core moiety. These compounds can efficiently be synthesized and show promising PK properties in rodents. (C) 2010 Elsevier Ltd. All rights reserved.
• DECAHYDRO-ISOQUINOLINES
  申请人：Novartis AG

  公开号：EP1268466B1

  公开（公告）日：2005-06-22
• US6635647B2
  申请人：——

  公开号：US6635647B2

  公开（公告）日：2003-10-21