| 454170-39-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• CAS: 454170-39-9
• 化学式: C₂₃H₂₈F₆N₂O₄
• 分子量: 510.477
• InChiKey: RLTDRPIXEKEUFW-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.72
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  67.87
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 盐酸 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 以86%的产率得到(3R)-3-Ethyl-2,3,4,7-tetrahydro-4-(2,2,2-trifluoroethyl)-10-(trifluoromethyl)-8H-[1,4]oxazino[2,3-f]quinolin-8-one
  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-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