2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline | 65623-40-7

• 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: 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline
• 英文别名: 2-(1,2,3,4-tetrahydroquinolin-2-yl)ethanol；2-(1,2,3,4-Tetrahydro-2-chinolyl)-ethanol；2-(1,2,3,4-Tetrahydroquinolin-2-yl)ethan-1-ol
• CAS: 65623-40-7
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: XYKHXADEXVAGSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline 在 氯化亚砜 、 二异丁基氢化铝 、 sodium cyanoborohydride 、 magnesium 、 溶剂黄146 、 lithium chloride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.25h， 生成 cuspareine
  参考文献：
  名称：

  Direct Aminoalkylation of Arenes, Heteroarenes, and Alkenes via Ni-Catalyzed Negishi Cross-Coupling Reactions

  摘要：

  A room-temperature Ni-catalyzed cross-coupling of aryl, heteroaryl, and alkenyl electrophiles with aminoalkylzinc bromides, readily available from the corresponding aminoalkyl chlorides via Grignard reagents, was developed. The reaction allows a convenient one-step preparation of various aminoalkyl products, including piperidine and tropane derivatives. Such functionalized amine moieties are widely present in various biologically active molecules. Aryl, heteroaryl, and alkenyl iodides, bromides, chlorides and triflates are suitable electrophiles. A short total synthesis of two natural products, (+/-)-galipinine and (+/-)-cusparine, is also reported.

  DOI：

  10.1021/jo201630e
• 作为产物：
  描述：

  2-(喹啉-2-基)乙酸乙酯 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 20.0 ℃ 、310.26 kPa 条件下， 反应 12.0h， 生成 2-(2-hydroxyethyl)-1,2,3,4-tetrahydroquinoline
  参考文献：
  名称：

  Syntheses and structure–activity relationship studies of piperidine-substituted quinolones as nonpeptide gonadotropin releasing hormone antagonists

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2003.12.101

文献信息

• Tetrahydroquinoline sulfonamides as vasopressin 1b receptor anatgonists
  作者：Jack D. Scott、Michael W. Miller、Sarah W. Li、Sue-Ing Lin、Henry A. Vaccaro、Liwu Hong、Deborra E. Mullins、Mario Guzzi、Jay Weinstein、Robert A. Hodgson、Geoffrey B. Varty、Andrew W. Stamford、Tin-Yau Chan、Brian A. McKittrick、William J. Greenlee、Tony Priestley、Eric M. Parker

  DOI：10.1016/j.bmcl.2009.09.050

  日期：2009.11

  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.
• Crabb, Trevor A.; Ingate, Simon T.; Nevell, Thomas G., Journal of Chemical Research, Miniprint, 1993, # 5, p. 1156 - 1167
  作者：Crabb, Trevor A.、Ingate, Simon T.、Nevell, Thomas G.

  DOI：——

  日期：——