13-Methyl-18-prop-2-enyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol | 1592683-24-3

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 阿朴菲
• 英文名称: 13-Methyl-18-prop-2-enyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol
• 英文别名: 13-methyl-18-prop-2-enyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol
• CAS: 1592683-24-3
• 化学式: C₂₁H₂₁NO₃
• 分子量: 335.403
• InChiKey: QRFXBFJZNPSLQZ-UHFFFAOYSA-N

物化性质

• 沸点：
  509.0±50.0 °C(predicted)
• 密度：
  1.276±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  41.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 1-[(6-bromo-1,3-benzodioxol-5-yl)methyl]-7-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate 在 lithium aluminium tetrahydride 、 di-tert-butyl(methyl)phosphonium tetrafluoroborate salt 、 palladium 10% on activated carbon 、 氢气 、 palladium diacetate 、 potassium carbonate 、 N,N-二乙基苯胺 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 乙腈 为溶剂， 反应 17.78h， 生成 13-Methyl-18-prop-2-enyl-5,7-dioxa-13-azapentacyclo[10.7.1.02,10.04,8.016,20]icosa-1(20),2,4(8),9,16,18-hexaen-19-ol
  参考文献：
  名称：

  Evaluation of structural effects on 5-HT2A receptor antagonism by aporphines: Identification of a new aporphine with 5-HT2A antagonist activity

  摘要：

  A set of aporphine analogs related to nantenine was evaluated for antagonist activity at 5-HT2A and alpha(1A) adrenergic receptors.With regards to 5-HT2A receptor antagonism, a C2 allyl group is detrimental to activity. The chiral center of nantenine is not important for 5-HT2A antagonist activity, however the N6 nitrogen atom is a critical feature for 5-HT2A antagonism.Compound 12b was the most potent 5-HT2A aporphine antagonist identified in this study and has similar potency to previously identified aporphine antagonists 2 and 3. The ring A and N6 modifications examined were detrimental to alpha(1A) antagonism. A slight eutomeric preference for the R enantiomer of nantenine was observed in relation to alpha(1A) antagonism. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.066