N-Acetyl polyveoline | 1239178-41-6

• 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: N-Acetyl polyveoline
• 英文别名: 1-[(1R,2S,10S,12S,13R,16R,18R)-16-hydroxy-1,13,17,17-tetramethyl-9-azapentacyclo[10.8.0.02,10.03,8.013,18]icosa-3,5,7-trien-9-yl]ethanone
• CAS: 1239178-41-6
• 化学式: C₂₅H₃₅NO₂
• 分子量: 381.558
• InChiKey: OGSHVAKUSGJWTH-FQBMDWTRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  28
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-Acetyl polyveoline 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以98.2%的产率得到O,N-diacetylpolyveoline
  参考文献：
  名称：

  Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae)

  摘要：

  The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.

  DOI：

  10.1016/j.phytochem.2014.06.015
• 作为产物：
  描述：

  (-)-episclareolide 在 正丁基锂 、 palladium 10% on activated carbon 、 montmorillonite K₁₀ Clay 、 sodium dibasic hypophosphite pentahydrate 、 C₂₁H₂₅N₇O₁₇P₃^(3-)*2H⁽¹⁺⁾*Na⁽¹⁺⁾ 、 氢气 、 乙酸酐 、 potassium tri-sec-butyl-borohydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 43.84h， 生成 N-Acetyl polyveoline 、 1-[(1R,2S,10S,12S,13R,16S,18R)-16-hydroxy-1,13,17,17-tetramethyl-9-azapentacyclo[10.8.0.02,10.03,8.013,18]icosa-3,5,7-trien-9-yl]ethanone
  参考文献：
  名称：

  一种基于手性池的策略来获取反式-syn-融合的 Drimane 类萜类化合物：多聚素、N-乙酰基-聚乙烯醇和 Chrodrimanins 的化学酶促全合成

  摘要：

  trans-syn -Fused drimane meroterpenoids 是独特的天然产物，其产生于它们的多烯前体的逆热力学多环化。在这里，我们报告了四种trans-syn融合的drimane meroterpenoids的首次总合成，即 polysin、 N-乙酰-polyveoline、chrodrimanin C 和 verruculide A，从 sclareolide 的 7-18 个步骤。反式-syn 融合的drimane 单元通过有效的酸介导的紫苏内酯 C9 差向异构化获得。酶促 C-H 氧化和现代环化方法的后续应用安装了必要的 C3 羟基，并能够快速生成结构复杂性，以提供对这些天然产物的简洁访问。

  DOI：

  10.1021/jacs.1c08696

文献信息

• A Chiral-Pool-Based Strategy to Access <i>trans-syn</i>-Fused Drimane Meroterpenoids: Chemoenzymatic Total Syntheses of Polysin, <i>N</i>-Acetyl-polyveoline and the Chrodrimanins
  作者：Fuzhuo Li、Hans Renata

  DOI：10.1021/jacs.1c08696

  日期：2021.11.3

  trans-syn-Fused drimane meroterpenoids are unique natural products that arise from contra-thermodynamic polycyclizations of their polyene precursors. Herein we report the first total syntheses of four trans-syn-fused drimane meroterpenoids, namely polysin, N-acetyl-polyveoline, chrodrimanin C, and verruculide A, in 7–18 steps from sclareolide. The trans-syn-fused drimane unit is accessed through an

  trans-syn -Fused drimane meroterpenoids 是独特的天然产物，其产生于它们的多烯前体的逆热力学多环化。在这里，我们报告了四种trans-syn融合的drimane meroterpenoids的首次总合成，即 polysin、 N-乙酰-polyveoline、chrodrimanin C 和 verruculide A，从 sclareolide 的 7-18 个步骤。反式-syn 融合的drimane 单元通过有效的酸介导的紫苏内酯 C9 差向异构化获得。酶促 C-H 氧化和现代环化方法的后续应用安装了必要的 C3 羟基，并能够快速生成结构复杂性，以提供对这些天然产物的简洁访问。
• Indolosesquiterpene alkaloids from the Cameroonian medicinal plant Polyalthia oliveri (Annonaceae)
  作者：Simeon Fogue Kouam、Alain Wembe Ngouonpe、Marc Lamshöft、Ferdinand Mouafo Talontsi、Jonathan O. Bauer、Carsten Strohmann、Bonaventure Tchaleu Ngadjui、Hartmut Laatsch、Michael Spiteller

  DOI：10.1016/j.phytochem.2014.06.015

  日期：2014.9

  The stem bark of Polyalthia oliveri was screened for its chemical constituents using liquid chromatography high resolution mass spectrometry resulting in the isolation of three indolosesquiterpene alkaloids named 8α-polyveolinone (1), N-acetyl-8α-polyveolinone (2) and N-acetyl-polyveoline (3), together with three known compounds, dehydro-O-methylisopiline (4), N-methylurabaine (5) and polycarpol (6). The structures of the compounds were elucidated by means of high resolution mass spectrometry and different NMR techniques and chemical transformations. Their absolute configurations were assigned by ab-initio calculation of CD and ORD data (for 2 and 3) and X-ray diffraction analysis (for 2). Compounds 2 and 3 exhibited moderate antiplasmodial activity against erythrocytic stages of chloroquine-sensitive Plasmodium falciparum NF54 strain and low cytotoxicity on rat skeletal myoblast (L6) cell line.