1,3,4,6,7,12b-hexahydro-2H-benzofuro<2,3-a>quinolizin-2-one | 98678-87-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1,3,4,6,7,12b-hexahydro-2H-benzofuro<2,3-a>quinolizin-2-one
• 英文别名: 3,4,5,6,7,12b-hexahydro-1H-benzofurano[3,2-h]quinolizin-2-one；1,3,4,6,7,12b-hexahydro-[1]benzofuro[2,3-a]quinolizin-2-one
• CAS: 98678-87-6
• 化学式: C₁₅H₁₅NO₂
• 分子量: 241.29
• InChiKey: ZRDWYECCNDBGMN-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  412.0±45.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  33.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3,4,6,7,12b-hexahydro-2H-benzofuro<2,3-a>quinolizin-2-one 在 sodium tetrahydroborate 、 四氯化钛 作用下， 以 乙醇 为溶剂， 生成 (2R,11bS)-1,3,4,5,6,11b-Hexahydro-2H-11-oxa-4a-aza-benzo[a]fluoren-2-yl-methyl-amine
  参考文献：
  名称：

  N-（1,3,4,6,7,12b-六氢-2H-苯并[b]呋喃[2,3-a]喹诺嗪-2-基）-N-甲基-2-羟基乙烷-磺酰胺和选择性α2肾上腺素受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00150a002
• 作为产物：
  描述：

  苯并呋喃-3-乙胺 在 三氟化硼乙醚 、 potassium carbonate 作用下， 生成 1,3,4,6,7,12b-hexahydro-2H-benzofuro<2,3-a>quinolizin-2-one
  参考文献：
  名称：

  N-（1,3,4,6,7,12b-六氢-2H-苯并[b]呋喃[2,3-a]喹诺嗪-2-基）-N-甲基-2-羟基乙烷-磺酰胺和选择性α2肾上腺素受体拮抗剂。

  摘要：

  DOI：

  10.1021/jm00150a002

文献信息

• A general synthesis of aryl[2,3-a]quinolizin-2-ones
  作者：J.P. Vacca

  DOI：10.1016/s0040-4039(00)94869-x

  日期：1985.1

  A convenient and general synthesis of arylquinolizines utilizing a hetero Diels-Alder reaction is described.

  描述了利用杂Diels-Alder反应方便且通用的芳基喹唑啉合成。
• Structure-affinity relationships of arylquinolizines at .alpha.-adrenoceptors
  作者：Joel R. Huff、John J. Baldwin、S. Jane DeSolms、James P. Guare、Cecilia A. Hunt、William C. Randall、William S. Sanders、Steven J. Smith、Joseph P. Vacca、Matthew M. Zrada

  DOI：10.1021/jm00398a025

  日期：1988.3

  Hexahydroaryl[a]quinolizines comprise a prominent structural element in several alpha 2-adrenoceptor antagonists. Eight hexahydroheteroarylquinolizines were prepared as minimal ligands to investigate the relationship between the nature of the aromatic ring and affinity of these molecules for alpha-adrenoceptors. Affinity for alpha 1-and alpha 2-adrenoceptors was assessed by displacement of [3H]prasozin and [3H]clonidine, respectively. Lipophilicity of the aryl portion of the molecules, reflected by their partition coefficient between octanol and pH 7.4 buffer, correlated well with affinity at both receptor subtypes. Although some compounds showed nanomolar affinity for alpha-adrenoceptors, no subtype selectivity was observed. These results suggest that the aromatic ring enhances binding at both receptors chiefly through hydrophobic interactions and contributes little to subtype selectivity.
• Synthesis of benzofuroquinolizine for α-2 adrenoceptor antagonist MK-912: an O-analogue of the Pictet-Spengler reaction
  作者：J Albaneze-Walker、K Rossen、R.A Reamer、R.P Volante、P.J Reider

  DOI：10.1016/s0040-4039(99)00840-0

  日期：1999.7

  Efficient synthesis of benzofuroquinolizine ketone 1 was accomplished in four steps from ethyl 3-benzofuranacetate. The O-analogue of the Pictet-Spengler cyclization was used to form the benzofuroquinolizine ring structure as a key step. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Enhanced reactivity of iminium ions as heterodienophiles in Lewis acid mediated 4+2 cycloaddition reactions
  作者：K.M Ryan、R.A Reamer、R.P Volante、I Shinkai

  DOI：10.1016/s0040-4039(00)96054-4

  日期：1987.1
• BALDWIN, JOHN J.;HUFF, JOEL R.;VACCA, JOSEPH P.;YOUNG, STEVEN D.;DE, SOLM+
  作者：BALDWIN, JOHN J.、HUFF, JOEL R.、VACCA, JOSEPH P.、YOUNG, STEVEN D.、DE, SOLM+

  DOI：——

  日期：——