gelsedine | 7096-96-0

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 钩吻生物碱
• 英文名称: gelsedine
• 英文别名: (Spiro(3H-indole-3,7'(6'H)-(3,) (6)methano(1H)oxepino(4,3-b)pyrrol)-2(1H)-one,) 2'-ethyl-2',3',3'a, 4',8',8'a-hexahydro-1-methoxy-；(1R,2S,4S,6R,7R,8S)-6-ethyl-1'-methoxyspiro[10-oxa-5-azatricyclo[5.3.1.04,8]undecane-2,3'-indole]-2'-one
• CAS: 7096-96-0
• 化学式: C₁₉H₂₄N₂O₃
• 分子量: 328.411
• InChiKey: LDBVYQSHIPCQPT-CTSQFDBHSA-N

物化性质

• 沸点：
  462.2±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  50.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  gelsenicine 在 platinum(IV) oxide 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 7.0h， 以95%的产率得到gelsedine
  参考文献：
  名称：

  统一的五种胶凝剂型生物碱的全合成：（-）-油菜青素，（-）-油菜素，（-）-油菜籽素，（-）-14-羟基胶体素和（-）-14,15-二羟基胶体素

  摘要：

  在非天然合成中间体的通用烯丙基部分上的两个碳原子单元，一个氢原子和一个氧原子的系统排列成功地导致了对凝胶状生物碱的统一访问。这种新的合成中枢的开发和使用以及一系列位点选择性转化导致（-）-gelsenicine，（-）-gelsedine，（-）-gelsedilam，（-）-14-hydroxygelsenicine和（-）-14，15-二羟基gelsenicine。

  DOI：

  10.1021/acs.orglett.6b02263

文献信息

• Unified Total Synthesis of Five Gelsedine-Type Alkaloids: (−)-Gelsenicine, (−)-Gelsedine, (−)-Gelsedilam, (−)-14-Hydroxygelsenicine, and (−)-14,15-Dihydroxygelsenicine
  作者：Takaaki Harada、Jun Shimokawa、Tohru Fukuyama

  DOI：10.1021/acs.orglett.6b02263

  日期：2016.9.16

  The systematic arrangement of a two-carbon unit, hydrogen atom, and oxygen atom on the versatile enal moiety of a non-natural synthetic intermediate successfully led to the unified access to the gelsedine-type alkaloids. The development and use of this new synthetic hub and an array of site-selective transformations resulted in the asymmetric synthesis of (−)-gelsenicine, (−)-gelsedine, (−)-gelsedilam

  在非天然合成中间体的通用烯丙基部分上的两个碳原子单元，一个氢原子和一个氧原子的系统排列成功地导致了对凝胶状生物碱的统一访问。这种新的合成中枢的开发和使用以及一系列位点选择性转化导致（-）-gelsenicine，（-）-gelsedine，（-）-gelsedilam，（-）-14-hydroxygelsenicine和（-）-14，15-二羟基gelsenicine。
• Anti-Inflammatory and Anti-Allergy Extracts from Nettle
  申请人：Alberte Randall S.

  公开号：US20100009927A1

  公开（公告）日：2010-01-14

  The present invention relates in part to nettle extracts that are useful for treating or preventing seasonal allergies, allergic rhinitis, and other inflammatory conditions.
• Extracts of Curcuma and Methods of Use Thereof
  申请人：Alberte Randall S.

  公开号：US20100098788A1

  公开（公告）日：2010-04-22

  The present invention relates in part to turmeric extracts that are useful for treating or preventing neurodegenerative disorders. Another aspect of the invention relates in part to turmeric extracts that are useful for treating or preventing inflammatory disorders. In some embodiments, the extracts comprise at least one compound selected from the group consisting of 25 to 500 μg bamosamine, 25 to 750 μg echinaxanthol, 100 to 3,000 μg bisdemethoxycurcumin, 50 to 500 μg daphniyunnine E and 500 to 75,000 μg curcumin per 100 mg of extract. Another aspect of the invention relates to pharmaceutical compositions comprising the aforementioned extracts. Another aspect of the invention relates to methods of treating or preventing neurodegenerative disorders comprising administering to a subject in need thereof an effective amount of the aforementioned extracts or compositions. Another aspect of the invention relates to methods of making the aforementioned extracts.
• [EN] ANTI-INFLAMMATORY AND ANTI-ALLERGY EXTRACTS FROM NETTLE<br/>[FR] EXTRAITS D'ORTIE ANTI-INFLAMMATOIRES ET ANTIALLERGIQUES
  申请人：HERBALSCIENCE GROUP LLC

  公开号：WO2010009091A2

  公开（公告）日：2010-01-21

  The present invention relates in part to nettle extracts that are useful for treating or preventing seasonal allergies, allergic rhinitis, and other inflammatory conditions.
• Divergent Entry to Gelsedine-Type Alkaloids: Total Syntheses of (−)-Gelsedilam, (−)-Gelsenicine, (−)-Gelsedine, and (−)-Gelsemoxonine
  作者：Pingluan Wang、Yang Gao、Dawei Ma

  DOI：10.1021/jacs.8b08127

  日期：2018.9.19

  possess a common oxabicyclo[3.2.2]nonane core and spiro- N-methoxyindolinone moiety along with a diversely functionalized heterocycle embedded in the compact framework. Herein we disclose a divergent entry to gelsedine-type alkaloids that hinges on rapid assembly of the common core by the orchestrated application of an asymmetric Michael addition, a tandem oxidation/aldol cyclization, and a pinacol rearrangement

  格尔西丁型生物碱具有共同的氧杂双环 [3.2.2] 壬烷核心和螺-N-甲氧基吲哚酮部分，以及嵌入紧凑框架中的多种功能化杂环。在本文中，我们公开了一种不同的进入gelsedine 型生物碱的方法，该方法取决于通过协调应用不对称迈克尔加成、串联氧化/羟醛环化和频哪醇重排以及通过后期的结构多样性的生成来快速组装共同核心。 -阶段杂环化。四种gelsedine 型生物碱的非常短的全合成证明了该策略的威力：gelsedilam、gelsenicine、gelsedine 和gelsemoxonine。