Tert-butyl 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate | 691857-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Tert-butyl 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate
• 英文别名: tert-butyl 2-(2-hydroxyethyl)-3,4-dihydro-2H-quinoline-1-carboxylate
• CAS: 691857-79-1
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: QDIUXQWGCAEYHC-UHFFFAOYSA-N

物化性质

• 沸点：
  398.9±21.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.77
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Tert-butyl 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists

  摘要：

  Vasopressin 1b (V1b) antagonists have been postulated as possible treatments for depression and anxiety. A novel series of potent and selective V1b antagonists has been identified starting from an in-house screen hit. The incorporation of a sulfonamide linker between a tetrahydroisoquinoline core and amino piperidine lead to the identification of a V1b antagonist with similar affinity for human and rat receptors. Further optimization of the right hand portion afforded potent V1b antagonists that possessed moderate to high selectivity over other receptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.050
• 作为产物：
  描述：

  在 锂硼氢 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 Tert-butyl 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline-1-carboxylate
  参考文献：
  名称：

  Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists

  摘要：

  Vasopressin 1b (V1b) antagonists have been postulated as possible treatments for depression and anxiety. A novel series of potent and selective V1b antagonists has been identified starting from an in-house screen hit. The incorporation of a sulfonamide linker between a tetrahydroisoquinoline core and amino piperidine lead to the identification of a V1b antagonist with similar affinity for human and rat receptors. Further optimization of the right hand portion afforded potent V1b antagonists that possessed moderate to high selectivity over other receptors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.050

文献信息

• Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists
  作者：Jinlong Jiang、Robert J. DeVita、Mark T. Goulet、Matthew J. Wyvratt、Jane-L. Lo、Ning Ren、Joel B. Yudkovitz、Jisong Cui、Yi T. Yang、Kang Cheng、Susan P. Rohrer

  DOI：10.1016/j.bmcl.2003.12.101

  日期：2004.4

  Syntheses and structure-activity relationships of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists are described. Some of substituents on the piperidine ring that were investigated included a fused phenyl group, a (6R)-trifluoromethyl group, (6S) and (6R)-methyl group. This study showed that GnRH binding potency was tolerated by a small group at the 6-position of the piperidine, and blocking the 6-position by a trifluoromethyl group reduced clearance rate and increased oral bioavailability. (C) 2004 Elsevier Ltd. All rights reserved.