6-cyano-5-methoxyacetamidoindan-1-one | 928208-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 6-cyano-5-methoxyacetamidoindan-1-one
• 英文别名: N-(6-cyano-1-oxo-2,3-dihydroinden-5-yl)-2-methoxyacetamide
• CAS: 928208-08-6
• 化学式: C₁₃H₁₂N₂O₃
• 分子量: 244.25
• InChiKey: QWABDKXCZGKSAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-cyano-5-methoxyacetamidoindan-1-one 在 sodium hydroxide 、 双氧水 作用下， 以 乙醇 、 水 为溶剂， 以96%的产率得到2-methoxymethyl-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazoline-4,6-dione
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092
• 作为产物：
  描述：

  5-methoxyacetamidoindane 在 tris(dibenzylideneacetone)dipalladium (0) chromium(VI) oxide 、 1,1'-双(二苯基膦)二茂铁 、 溴 、 2,4-滴二甲胺盐 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 3.75h， 生成 6-cyano-5-methoxyacetamidoindan-1-one
  参考文献：
  名称：

  Cyclopenta[g]quinazolinone-based inhibitors of thymidylate synthase targeting α-folate receptor overexpressing tumours: synthetic approaches to 4-{N-[(6RS)-2-hydroxymethyl-4-oxo-3,4,7,8-tetrahydro-6H-cyclopenta[g]quinazolin-6-yl]-N-(prop-2-ynyl)amino}benzoic acid

  摘要：

  An advanced intermediate for the synthesis of cyclopenta[g]quinazolinone-based antifolates such as (6RS)-CB300945 was prepared by a convergent methodology. The oxo-functionality required for the formation of the C-6-N-10 bond in 4 was introduced in the initial steps of the synthesis, then the tricyclic ring was constructed and finally the propargyl group was introduced using the (propargyl)CO2(CO)(6)(+) complex without the need to protect the N-3-H or 2-hydroxymethyl functionalities. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.11.092