3-benzyloxycarbonylamino-4-methylen-5-trifluoroacetamide-chromane | 1309370-77-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-benzyloxycarbonylamino-4-methylen-5-trifluoroacetamide-chromane
• CAS: 1309370-77-1
• 化学式: C₂₀H₁₇F₃N₂O₄
• 分子量: 406.361
• InChiKey: AECCUKFYPHQJQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 3-benzyloxycarbonylamino-4-methylen-5-trifluoroacetamide-chromane 在 羟基甲苯磺酰碘苯 作用下， 反应 4.0h， 生成 3-benzyloxycarbonylamino-4-hydroxy-4-methoxy-6-(2,2,2-trifluoroacetamido)-2,3,4,5-tetrahydrobenzo[b]oxepine 、 3-benzyloxycarbonylamino-4-hydroxy-4-methoxy-6-(2,2,2-trifluoroacetamido)-2,3,4,5-tetrahydrobenzo[b]oxepine
  参考文献：
  名称：

  An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family

  摘要：

  Derivatives from the aminobenzosuberone family have been recently synthesized and recognized as highly selective inhibitors of aminopeptidase N (APN)/CD13 (EC 3.4.11.2), an important target for cell migration processes involved in particular in tumor invasion. We present here a much more straightforward synthesis of analogues belonging to a novel isosteric oxo series which also possesses excellent inhibitory potential against APN. Their synthesis, as reported here, relied on an interesting iodine(III)-mediated rearrangement originally described by Koser and Justik as the key step. This represents the second application of this rearrangement in medicinal chemistry. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.03.043
• 作为产物：
  描述：

  3-benzyloxycarbonylamino-4-methylen-5-nitro-chromane 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 8.0h， 生成 3-benzyloxycarbonylamino-4-methylen-5-trifluoroacetamide-chromane
  参考文献：
  名称：

  An innovative strategy for the synthesis of a new series of potent aminopeptidase (APN or CD13) inhibitors derived from the oxepin-4-one family

  摘要：

  Derivatives from the aminobenzosuberone family have been recently synthesized and recognized as highly selective inhibitors of aminopeptidase N (APN)/CD13 (EC 3.4.11.2), an important target for cell migration processes involved in particular in tumor invasion. We present here a much more straightforward synthesis of analogues belonging to a novel isosteric oxo series which also possesses excellent inhibitory potential against APN. Their synthesis, as reported here, relied on an interesting iodine(III)-mediated rearrangement originally described by Koser and Justik as the key step. This represents the second application of this rearrangement in medicinal chemistry. (C) 2011 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2011.03.043