N-(6-bromonaphthalen-2-yl)pent-4-ynamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(6-bromonaphthalen-2-yl)pent-4-ynamide
• 化学式: C₁₅H₁₂BrNO
• 分子量: 302.17
• InChiKey: VUCLXHLKHLFSNI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(6-bromonaphthalen-2-yl)pent-4-ynamide 、 4-戊基苯乙炔 在 silver hexafluoroantimonate 、 gold(III) bromide 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以12%的产率得到8-bromo-12a-methyl-11-(4-pentylphenyl)-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-one
  参考文献：
  名称：

  Concise synthesis of 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones as racemic 14-azaestrogen analogs

  摘要：

  A concise method for the synthesis of 14-azasteroid analogs with angular methyl group at C-13 of the steroidal nucleus has been reported in this paper. We have developed an interesting cascade reaction of arylacetylenes and N-(naphthalen-2-yl)pent-4-ynamides under gold (III)-catalysis to produce novel tetracyclic 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones which may be viewed as 14-azaestrogen analogs. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.03.010
• 作为产物：
  描述：

  6-溴-2-萘酚 在 ammonium hydroxide 、 ammonium sulfite monohydrate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 34.0h， 生成 N-(6-bromonaphthalen-2-yl)pent-4-ynamide
  参考文献：
  名称：

  Concise synthesis of 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones as racemic 14-azaestrogen analogs

  摘要：

  A concise method for the synthesis of 14-azasteroid analogs with angular methyl group at C-13 of the steroidal nucleus has been reported in this paper. We have developed an interesting cascade reaction of arylacetylenes and N-(naphthalen-2-yl)pent-4-ynamides under gold (III)-catalysis to produce novel tetracyclic 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones which may be viewed as 14-azaestrogen analogs. (C) 2015 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.steroids.2015.03.010

文献信息

• Concise synthesis of 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones as racemic 14-azaestrogen analogs
  作者：Ashraf M. Abdelkhalik、Nawal K. Paul、Amitabh Jha

  DOI：10.1016/j.steroids.2015.03.010

  日期：2015.6

  A concise method for the synthesis of 14-azasteroid analogs with angular methyl group at C-13 of the steroidal nucleus has been reported in this paper. We have developed an interesting cascade reaction of arylacetylenes and N-(naphthalen-2-yl)pent-4-ynamides under gold (III)-catalysis to produce novel tetracyclic 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones which may be viewed as 14-azaestrogen analogs. (C) 2015 Elsevier Inc. All rights reserved.