(3S,16R)-14-(methoxycarbonyl)-15-oxoeburnane | 95464-01-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - Eburnan型生物碱
• 英文名称: (3S,16R)-14-(methoxycarbonyl)-15-oxoeburnane
• CAS: 95464-01-0
• 化学式: C₂₁H₂₄N₂O₃
• 分子量: 352.433
• InChiKey: HRLQCHUUDOXADO-WVYCPIKRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  51.54
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,16R)-14-(methoxycarbonyl)-15-oxoeburnane 在 sodium tetrahydroborate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.55h， 生成 阿扑长春胺
  参考文献：
  名称：

  Synthesis of optically pure pipecolates from L-asparagine. Application to the total synthesis of (+)-apovincamine through amino acid decarbonylation and iminium ion cyclization

  摘要：

  DOI：

  10.1021/jo00208a017
• 作为产物：
  描述：

  12-epi-1-ethyl-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizine-1-carbonitrile 在 sodium hydride 、 三氟乙酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 35.25h， 生成 (3S,16R)-14-(methoxycarbonyl)-15-oxoeburnane
  参考文献：
  名称：

  Synthesis of optically pure pipecolates from L-asparagine. Application to the total synthesis of (+)-apovincamine through amino acid decarbonylation and iminium ion cyclization

  摘要：

  DOI：

  10.1021/jo00208a017

文献信息

• Studies on the synthesis, structural characterization, Hirshfeld analysis and stability of apovincamine (API) and its co-crystal (terephthalic acid: Apovincamine=1:2)
  作者：Yu-heng Ma、Shu-wang Ge、Wei Wang、Bai-wang Sun

  DOI：10.1016/j.molstruc.2015.05.014

  日期：2015.10

  Apovincamine and the corresponding co-crystal have been synthesized and characterized by single crystal XRD, FT-IR, UV, TGA/DSG. Components of the crystalline phase have also been investigated in terms of their corresponding Hirshfeld surface. In the crystal lattice, a three-dimensional hydrogen-bonded network is observed in the co-crystal, including the formation of a two-dimensional molecular scaffold. Hirshfeld surfaces and fingerprint plots indicate that the structures are stabilized by H center dot center dot center dot H, C-H center dot center dot center dot pi, C-H center dot center dot center dot O and O-H center dot center dot center dot N intermolecular interactions. In this work, the co-crystal strategy has been applied successfully to apovincamine. One important parameter, i.e. solubility in water, has also been significantly improved, which proves to be an important factor for bioavailability. Furthermore, DSC/TGA analysis indicates that the co-crystal maintains its crystallinity up to 200 degrees C, suggesting a higher stability of the co-crystal compared to apovincamine. (C) 2015 The Authors. Published by Elsevier B.V. This is an open access article under the CC BY license (http://creativecommons.org/licenses/by/4.0/).