meloscine | 24314-51-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 山橙属生物碱
• 英文名称: meloscine
• 英文别名: (1R,10S,12S,19S)-12-ethenyl-8,16-diazapentacyclo[10.6.1.01,10.02,7.016,19]nonadeca-2,4,6,13-tetraen-9-one
• CAS: 24314-51-0
• 化学式: C₁₉H₂₀N₂O
• 分子量: 292.381
• InChiKey: BEMFQIDPZLYEBJ-FCLVOEFKSA-N

物化性质

• 熔点：
  172-176 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  485.7±45.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  tert-butyl 4-(2-(2,2-divinylcyclopropanecarboxamido)phenyl)-2,3-dihydro-1H-pyrrole-1-carboxylate 在 Hoveyda-Grubbs catalyst second generation 、 偶氮二异丁腈 、 potassium tert-butylate 、 三正丁基氢锡 、 potassium carbonate 、 三氟乙酸 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 、 叔丁醇 为溶剂， 生成 meloscine
  参考文献：
  名称：

  Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids

  摘要：

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.09.016

文献信息

• Total Synthesis of Meloscine by a [2+2]-Photocycloaddition/Ring-Expansion Route
  作者：Philipp Selig、Eberhardt Herdtweck、Thorsten Bach

  DOI：10.1002/chem.200802383

  日期：2009.3.23

  The stereogenic centers at C3 and C12 of meloscine (3) can be established in the photochemical key step 1 → 2. 1,2‐retro‐Benzilic acid rearrangement to a five‐membered ring, reductive amination, Claisen rearrangement, and ring‐closing metathesis are further key steps in the transformation of cyclobutane 2 into the target molecule 3 (14 steps, 9 % overall yield). Enantioselective access to (+)‐meloscine

  可以在光化学关键步骤1 → 2中建立甲磺胺（3）的C3和C12的立体定向中心。1,2-复古-Benzilic酸重排一个五元环，还原性胺化，Claisen重排，和闭环复分解是在环丁烷的转化进一步关键步骤2到目标分子3（14个步骤，9％总产率）。当[2 + 2]-光环加成反应是在手性模板存在下进行时，对映体可以选择性地与（+）-肌氨酸结合。
• Enantioselective Total Synthesis of the<i>Melodinus</i>Alkaloid (+)-Meloscine
  作者：Philipp Selig、Thorsten Bach

  DOI：10.1002/anie.200800693

  日期：2008.6.23
• Highly functionalized donor–acceptor cyclopropanes applied toward the synthesis of the Melodinus alkaloids
  作者：Alexander F.G. Goldberg、Robert A. Craig、Nicholas R. O’Connor、Brian M. Stoltz

  DOI：10.1016/j.tetlet.2014.09.016

  日期：2015.6

  A series of highly substituted vinylcyclopropanes were prepared and examined as reaction partners in a palladium-catalyzed (3+2) cycloaddition with nitrostyrenes. Described herein are our efforts to synthesize an elusive 1,1-divinylcyclopropane by several distinct approaches, and to apply surrogates of this fragment toward the synthesis of the Melodious alkaloids. (C) 2014 Elsevier Ltd. All rights reserved.