(3R)-(-)-3-ethyl-3,4-dihydro-8-(trifluoroacetyl)-4-(2,2,2-trifluoroethyl)-7-(trimethylacetamido)-2H-1,4-benzoxazine | 454170-38-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (3R)-(-)-3-ethyl-3,4-dihydro-8-(trifluoroacetyl)-4-(2,2,2-trifluoroethyl)-7-(trimethylacetamido)-2H-1,4-benzoxazine
• 英文别名: (3R)-3beta-Ethyl-4-(2,2,2-trifluoroethyl)-7-(pivaloylamino)-8-(trifluoroacetyl)-3,4-dihydro-2H-1,4-benzooxazine；N-[(3R)-3-ethyl-8-(2,2,2-trifluoroacetyl)-4-(2,2,2-trifluoroethyl)-2,3-dihydro-1,4-benzoxazin-7-yl]-2,2-dimethylpropanamide
• CAS: 454170-38-8
• 化学式: C₁₉H₂₂F₆N₂O₃
• 分子量: 440.386
• InChiKey: OHXYFPIMKZTNNT-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (3R)-(-)-3-ethyl-3,4-dihydro-8-(trifluoroacetyl)-4-(2,2,2-trifluoroethyl)-7-(trimethylacetamido)-2H-1,4-benzoxazine 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 反应 4.0h， 以93%的产率得到
  参考文献：
  名称：

  Efficient synthesis of an androgen receptor modulator

  摘要：

  An efficient synthesis of the androgen receptor modulator (R)-4a having an 8H-[1,4]oxazino[2,3-f]quinolin-8-one skeleton is described. Synthesis of this ring system, not readily accessible by classical Knorr cyclization methodology, was accomplished by an ortho-metallation strategy. Thus, lithiation of a pivaloyl-protected 7-amino-3,4-dihydro-1,4-benzoxazine using n-butyllithium allowed the introduction of a trifluoroacetyl group regioselectively at the 8-position. Subsequent Wittig reaction and acid catalyzed cyclization afforded the desired 8H-[1,4]oxazino[2,3-f]quinolin-8-one (R)-4a in very good overall yield from the corresponding benzoxazine. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.114
• 作为产物：
  描述：

  (3R)-3-Ethyl-3,4-dihydro-4-(2,2,2-trifluoroethyl)-7-(trimethylacetamido)-2H-1,4 benzoxazine 、 三氟乙酸乙酯 在 正丁基锂 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以56%的产率得到(3R)-(-)-3-ethyl-3,4-dihydro-8-(trifluoroacetyl)-4-(2,2,2-trifluoroethyl)-7-(trimethylacetamido)-2H-1,4-benzoxazine
  参考文献：
  名称：

  Efficient synthesis of an androgen receptor modulator

  摘要：

  An efficient synthesis of the androgen receptor modulator (R)-4a having an 8H-[1,4]oxazino[2,3-f]quinolin-8-one skeleton is described. Synthesis of this ring system, not readily accessible by classical Knorr cyclization methodology, was accomplished by an ortho-metallation strategy. Thus, lithiation of a pivaloyl-protected 7-amino-3,4-dihydro-1,4-benzoxazine using n-butyllithium allowed the introduction of a trifluoroacetyl group regioselectively at the 8-position. Subsequent Wittig reaction and acid catalyzed cyclization afforded the desired 8H-[1,4]oxazino[2,3-f]quinolin-8-one (R)-4a in very good overall yield from the corresponding benzoxazine. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.01.114

文献信息

• Tricyclic quinolinone and tricyclic quinoline androgen receptor modulator compounds and methods
  申请人：Ligand Pharmaceuticals Incorporated

  公开号：US20020183314A1

  公开（公告）日：2002-12-05

  Novel non-steroidal tricyclic quinolinone and tricyclic quinoline compounds and compositions that are agonists, partial agonists and/or antagonists for androgen receptors (AR), their preparation and their uses are described.

  描述了一种新型的非甾体三环喹诺酮和三环喹啉化合物以及对雄激素受体（AR）具有激动剂、部分激动剂和/或拮抗剂作用的组合物，以及它们的制备和用途。
• TRICYCLIC QUINOLINONE AND TRICYCLIC QUINOLINE AS ANDROGEN RECEPTOR MODULATOR COMPOUNDS
  申请人：LIGAND PHARMACEUTICALS INCORPORATED

  公开号：EP1368357A1

  公开（公告）日：2003-12-10
• US7214690B2
  申请人：——

  公开号：US7214690B2

  公开（公告）日：2007-05-08
• [EN] TRICYCLIC QUINOLINONE AND TRICYCLIC QUINOLINE AS ANDROGEN RECEPTOR MODULATOR COMPOUNDS<br/>[FR] QUINOLINONE TRICYCLIQUE ET QUINOLEINE TRICYCLIQUE UTILISEES COMME COMPOSES MODULATEURS DES RECEPTEURS ANDROGENIQUES
  申请人：LIGAND PHARM INC

  公开号：WO2002068427A1

  公开（公告）日：2002-09-06

  Novel non-steroidal tricyclic quinolinone and tricyclic quinoline compounds and compositions that are agonists, partial agonists and/or antagonists for androgen receptors (AR), their preparation and their uses are described.