2-(tert-butyl) 4-ethyl (4S,4aS,8aR)-octahydroisoquinoline-2,4(1H)-dicarboxylate | 646518-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(tert-butyl) 4-ethyl (4S,4aS,8aR)-octahydroisoquinoline-2,4(1H)-dicarboxylate
• 英文别名: (4S,4aS,8aR)-Octahydro-isoquinoline-2,4-dicarboxylic acid 2-tert-butyl ester 4-ethyl ester
• CAS: 646518-37-8
• 化学式: C₁₇H₂₉NO₄
• 分子量: 311.422
• InChiKey: DPBXZJZWBOPABK-MELADBBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.22
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-(tert-butyl) 4-ethyl (4S,4aS,8aR)-octahydroisoquinoline-2,4(1H)-dicarboxylate 在 lithium hydroxide 、 potassium carbonate 、 N,N'-羰基二咪唑 、 三氟乙酸 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 213.0h， 生成 [4-(3,4-difluorophenyl)-piperazin-1-yl]-{(4s,4aS,8aR)-2-[(S)-3-(6-methoxy-pyridin-3-yl)-2-methyl-propyl]-decahydro-isoquinolin-4-yl}-methanone
  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：

  二碳酸二叔丁酯 、 (4S,4aS,8aR)-decahydro-isoquinoline-4-carboxylic acid ethyl ester 以 乙醇 为溶剂， 反应 2.0h， 生成 2-(tert-butyl) 4-ethyl (4S,4aS,8aR)-octahydroisoquinoline-2,4(1H)-dicarboxylate
  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

文献信息

• 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.