1,1-dimethylethyl (3S)-3-(2-hydroxymethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate | 691857-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: 1,1-dimethylethyl (3S)-3-(2-hydroxymethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
• 英文别名: tert-butyl (3S)-3-(2-hydroxyethyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate；tert-butyl (3S)-3-(2-hydroxyethyl)-3,4-dihydro-1H-isoquinoline-2-carboxylate
• CAS: 691857-77-9
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: HNQRKOSPIWUPBG-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,1-dimethylethyl (3S)-3-(2-hydroxymethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以67%的产率得到1,1-dimethylethyl (3S)-3-(2-bromoethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
  参考文献：
  名称：

  WO2006/113837

  摘要：

  公开号：
• 作为产物：
  描述：

  N-叔丁氧羰基-(S)-1,2,3,4-四氢异喹啉-3-羧酸 在 lithium aluminium tetrahydride 、 TEA 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 9.0h， 生成 1,1-dimethylethyl (3S)-3-(2-hydroxymethyl)-3,4-dihydro-2(1H)-isoquinolinecarboxylate
  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

• WO2006/113837
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.