(S)-3-(6-methoxy-pyridin-3-yl)-2-methylpropionic acid methyl ester | 646518-41-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-3-(6-methoxy-pyridin-3-yl)-2-methylpropionic acid methyl ester
• CAS: 646518-41-4
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: IWLCRQRROZVXMU-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  15.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  48.42
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-3-(6-methoxy-pyridin-3-yl)-2-methylpropionic acid methyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (S)-3-(6-methoxy-pyridin-3-yl)-2-methylpropan-1-ol
  参考文献：
  名称：

  Decahydroisoquinoline derivatives as novel non-peptidic, potent and subtype-selective somatostatin sst3 receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.01.063
• 作为产物：
  描述：

  5-溴-2-甲氧基吡啶 、 (R)-(+)-3-溴异丁酸甲酯 在 manganese(II) bromide 、 diethylzinc 、 copper(l) chloride 、 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 N,N-二甲基丙烯基脲 为溶剂， 反应 4.0h， 生成 (S)-3-(6-methoxy-pyridin-3-yl)-2-methylpropionic acid methyl ester
  参考文献：
  名称：

  Decahydroisoquinoline derivatives as novel non-peptidic, potent and subtype-selective somatostatin sst3 receptor antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2010.01.063

文献信息

• 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)
  作者：Markus Bänziger、Jacques Cercus、Hans Hirt、Kurt Laumen、Christophe Malan、Felix Spindler、Fritz Struber、Thomas Troxler

  DOI：10.1016/j.tetasy.2003.07.024

  日期：2003.11

  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.
• C-14, C-13, H-2 labeling of NVP-ACQ090 – a potent and selective somastatin sst3-receptor antagonist
  作者：Thomas Moenius、Thomas Troxler、Rolf Masero

  DOI：10.1002/jlcr.1308

  日期：2007.4
• 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.