Nb-acetoacetyl-5-methoxytryptamine | 112081-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: Nb-acetoacetyl-5-methoxytryptamine
• 英文别名: N-<2-(5-methoxy-1H-indol-3-yl)ethyl>-3-oxobutyramide；N-(2-(5-methoxy-1H-indol-3-yl)ethyl)-3-oxobutanamide；N-(2-(5-Methoxy-1H-indol-3-yl)ethyl)-3-oxobutanamide；N-[2-(5-methoxy-1H-indol-3-yl)ethyl]-3-oxobutanamide
• CAS: 112081-40-0
• 化学式: C₁₅H₁₈N₂O₃
• 分子量: 274.32
• InChiKey: NMQJDEDRZIUFBH-UHFFFAOYSA-N

物化性质

• 沸点：
  562.7±50.0 °C(Predicted)
• 密度：
  1.204±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  71.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Nb-acetoacetyl-5-methoxytryptamine 在 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以68%的产率得到(9bS,9cS)-8-Methoxy-5-methyl-1,2,9b,9c-tetrahydro-2a,5a-diaza-cyclopenta[jk]fluoren-3-one
  参考文献：
  名称：

  2a，5a-二氮杂双环[ jk ]芴环系统的新颖两阶段路线

  摘要：

  通过磷酰氯介导的色胺与双烯酮的缩合产物的环化反应合成了标题环系统。

  DOI：

  10.1039/c39870000653
• 作为产物：
  描述：

  1-hydroxy-Nb-methoxycarbonyltryptamine 在 吡啶 、 sodium hydroxide 、 正丁基锂 、 三氟化硼 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 10.34h， 生成 Nb-acetoacetyl-5-methoxytryptamine
  参考文献：
  名称：

  Syntheses of Melatonin and Its Derivatives

  摘要：

  Two simple synthetic methods for melatonin are newly developed from tryptamine through intermediates, which are promising lead compounds for drug developing research. Novel chemical reactivities of melatonin in its bromination, lithiation, and acylation are also reported.

  DOI：

  10.3987/com-00-8930

文献信息

• Enantioselective organocatalyzed cascade reactions to highly functionalized quinolizidines
  作者：Xiaoyang Dai、Xiaoyu Wu、Huihui Fang、Linlin Nie、Jie Chen、Hongmei Deng、Weiguo Cao、Gang Zhao

  DOI：10.1016/j.tet.2011.03.007

  日期：2011.4

  An organocatalyzed one-pot Michael addition-Pictet–Spengler sequence of β-ketoamides and α,β-unsaturated aldehydes was developed, which provided access to highly substituted indolo[2,3-α]quinolizidines and benzo[α]quinolizidines in moderate to good yields and good to excellent enantioselectivities. For aromatic α,β-unsaturated aldehydes 1a–j products 10a–r containing a stable enol configuration were

  研发了一种有机催化的一锅法的β-酮酰胺和α，β-不饱和醛的Michael加成-Pictet-Spengler序列，它提供了以中等至中等的程度取代高取代度的吲哚[2,3-α]喹啉和苯并[α]喹啉的途径。良好的产率和良好至优异的对映选择性。对于含有稳定的烯醇构型的芳族α，β-不饱和醛1a – j产物10a – r。
• Multi-target 1,4-dihydropyridines showing calcium channel blockade and antioxidant capacity for Alzheimer’s disease therapy
  作者：Rim Malek、Maciej Maj、Artur Wnorowski、Krzysztof Jóźwiak、Helene Martin、Isabel Iriepa、Ignacio Moraleda、Fakher Chabchoub、José Marco-Contelles、Lhassane Ismaili

  DOI：10.1016/j.bioorg.2019.103205

  日期：2019.10

  In this work we describe the synthesis, Ca+2 channel blockade capacity and antioxidant power of N-3, N-5-bis(2-(5-methoxy-1H-indol-3-yl) ethyl)-2,6-dimethyl-4-aryl-1,4-dihydropyridine-3,5-dicarboxamides 1-9, a number of multi-target small 1,4-dihydropyridines (DHP), designed by juxtaposition of melatonin and nimodipine. As a result, we have identified antioxidant DHP 7 (Ca2+ channel blockade: 55%, and 8.78 Trolox/Equivalents), the most balanced DHP analyzed here, for potential Alzheimer's disease therapy.
• Wilkins, David J.; Jackson, Anthony H.; Shannon, Patrick V. R., Journal of the Chemical Society. Perkin transactions I, 1994, # 3, p. 299 - 308
  作者：Wilkins, David J.、Jackson, Anthony H.、Shannon, Patrick V. R.

  DOI：——

  日期：——
• US9738605B2
  申请人：——

  公开号：US9738605B2

  公开（公告）日：2017-08-22
• Syntheses of Melatonin and Its Derivatives
  作者：Masanori Somei、Yoshikazu Fukui、Masakazu Hasegawa、Naoki Oshikiri、Toshikatsu Hayashi

  DOI：10.3987/com-00-8930

  日期：——

  Two simple synthetic methods for melatonin are newly developed from tryptamine through intermediates, which are promising lead compounds for drug developing research. Novel chemical reactivities of melatonin in its bromination, lithiation, and acylation are also reported.