(E)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile | 333748-92-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile
• 英文别名: trans-2,3,4,6-Tetra-O-acetylalliarinoside；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E)-3-cyanoprop-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 333748-92-8
• 化学式: C₁₈H₂₃NO₁₀
• 分子量: 413.381
• InChiKey: IZTCRAZMRMVXSX-ZDDPQDGSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  147
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (E)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile 在 甲醇 、 potassium carbonate 作用下， 反应 4.0h， 生成 (2E)-4-(β-D-Glucopyranosyloxy)-2-butenenitrile
  参考文献：
  名称：

  A Cyanoallyl Glucoside from Alliaria petiolata, as a Feeding Deterrent for Larvae of Pieris napi oleracea

  摘要：

  Alliarinoside, a feeding inhibitor against early instar larvae of Pieris napi oleracea, was isolated from the foliage of Alliaria petiolata and characterized as (2Z)-4-(beta -D-glucopyranosyloxy)-2-butenenitrile (1) by spectroscopic methods. The structural assignment was confirmed by synthesis of peracetylated alliarinoside (2) and its 2E isomer (3). A sample of synthetic 1 was isolated by preparative HPLC from the hydrolysis of the 2Z acetate. Feeding inhibition assays showed comparable activity for the synthetic and natural glycosides.

  DOI：

  10.1021/np000534d
• 作为产物：
  描述：

  2,3-epoxypropyl tetra-O-acetyl-β-D-glucopyranoside 在 吡啶 、 lithium perchlorate trihydrate 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 1.0h， 生成 (E)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)but-2-enenitrile
  参考文献：
  名称：

  Synthesis of the allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America

  摘要：

  The allelochemical alliarinoside present in garlic mustard (Alliaria petiolata), an invasive plant species in North America, was chemically synthesized using an efficient and practical synthetic strategy based on a simple reaction sequence. Commercially available 1,2,3,4,6-penta-O-acetyl-beta-D-glucopyranose was converted into prop-2-enyl 2',3',4',6'-tetra-O-acetyl-beta-D-glucopyranoside and subjected to epoxidation. In a one-pot reaction, ring-opening of the epoxide using TMSCN under solvent free conditions followed by treatment of the formed trimethylsilyloxy nitrile with pyridine and phosphoryl chloride, afforded the acetylated beta-unsaturated nitriles (Z)-4-(2',3',4',6'-tetra-O-beta-D-glucopyranosyloxy)but-2-enenitrile and its isomer (E)-4-(2',3',4',6'-tetra-O-beta-D-glucopyranosyloxy)but-2-enenitrile. Deacetylation of Z-and/or E-isomers afforded the target molecules alliarinoside and its isomer. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.006