daphnicyclidin F | 385384-26-9

• 物质功能分类: 天然产物 - 生物碱
• 分子结构分类: 有机化合物 - 碳氢化合物 - 不饱和烃
• 英文名称: daphnicyclidin F
• 英文别名: methyl (2S,3R,5S,6R,10S)-5-hydroxy-2,6-dimethyl-21-oxo-14-oxa-8-azahexacyclo[11.6.1.15,19.02,10.03,8.017,20]henicosa-1(19),13(20),17-triene-18-carboxylate
• CAS: 385384-26-9
• 化学式: C₂₃H₂₇NO₅
• 分子量: 397.471
• InChiKey: CBULSUOPAXBENF-VBIFSVJFSA-N

物化性质

• 沸点：
  604.7±55.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  76.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  daphnicyclidin F 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 48.0h， 以0.6 mg的产率得到daphnicyclidin G
  参考文献：
  名称：

  Daphnicyclidins A−H, Novel Hexa- or Pentacyclic Alkaloids from Two Species of Daphniphyllum

  摘要：

  Eight highly modified Daphniphyllum alkaloids with unprecedented fused hexa- or pentacyclic skeletons, daphnicyclidins A-H (1-8), have been isolated from the stems of Daphniphyllum humile and D. teijsmanni, and their structures were elucidated on the basis of spectroscopic data and chemical means. The stereochemistry was elucidated by combination of NOESY correlations, X-ray crystallographic data, and CD analyses.

  DOI：

  10.1021/ja016955e
• 作为产物：
  描述：

  达菲环素D 在 氢氧化钾 、 碘苯二乙酸 作用下， 以 水 、 苯 为溶剂， 反应 48.0h， 以0.2 mg的产率得到daphnicyclidin F
  参考文献：
  名称：

  Daphnicyclidins A−H, Novel Hexa- or Pentacyclic Alkaloids from Two Species of Daphniphyllum

  摘要：

  Eight highly modified Daphniphyllum alkaloids with unprecedented fused hexa- or pentacyclic skeletons, daphnicyclidins A-H (1-8), have been isolated from the stems of Daphniphyllum humile and D. teijsmanni, and their structures were elucidated on the basis of spectroscopic data and chemical means. The stereochemistry was elucidated by combination of NOESY correlations, X-ray crystallographic data, and CD analyses.

  DOI：

  10.1021/ja016955e

文献信息

• Total Synthesis of Four Classes of <i>Daphniphyllum</i> Alkaloids
  作者：Wenhao Zhang、Ming Lu、Lu Ren、Xiang Zhang、Shaonan Liu、Mengyu Ba、Peng Yang、Ang Li

  DOI：10.1021/jacs.3c06088

  日期：2023.12.13

  macrodaphniphyllamine-type, calyciphylline A-type, daphnilongeranin A-type, and daphnicyclidin D-type alkaloids are four structurally related classes of Daphniphyllum alkaloids. On the basis of a systematic analysis of the biogenetic network of these classes, we developed synthetic strategies centered on the C4–N and C1–C8 bonds of calyciphylline A, which took full advantage of the suitable substrates

  大瑞香胺型、金盏花碱 A 型、瑞香 A 型和瑞环素 D 型生物碱是四类结构相关的瑞香生物碱。在对这些类别的生物遗传网络进行系统分析的基础上，我们开发了以calyciphylline A的C4-N和C1-C8键为中心的合成策略，该策略充分利用了合适的底物、反应和被改变的途径来自假定的生物遗传网络中的对应物。通过这种广义的仿生方法，我们首次合成了来自四个亚科的 14 种瑞香生物碱。
• Daphnicyclidins A−H, Novel Hexa- or Pentacyclic Alkaloids from Two Species of <i>Daphniphyllum</i>
  作者：Jun'ichi Kobayashi、Yasutada Inaba、Motoo Shiro、Naotoshi Yoshida、Hiroshi Morita

  DOI：10.1021/ja016955e

  日期：2001.11.1

  Eight highly modified Daphniphyllum alkaloids with unprecedented fused hexa- or pentacyclic skeletons, daphnicyclidins A-H (1-8), have been isolated from the stems of Daphniphyllum humile and D. teijsmanni, and their structures were elucidated on the basis of spectroscopic data and chemical means. The stereochemistry was elucidated by combination of NOESY correlations, X-ray crystallographic data, and CD analyses.