4-cyanocinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 857500-54-0

• 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: 4-cyanocinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(E)-3-(4-cyanophenyl)prop-2-enoxy]oxan-2-yl]methyl acetate
• CAS: 857500-54-0
• 化学式: C₂₄H₂₇NO₁₀
• 分子量: 489.479
• InChiKey: LRHYZPXUMRREHX-PURUWYKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  35
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 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：

  4-cyanocinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以99%的产率得到4-cyanocinnamyl β-D-glucopyranoside
  参考文献：
  名称：

  Simple synthesis of phenylpropenoid β-d-glucopyranoside congeners based on Mizoroki–Heck type reaction of organoboron reagents

  摘要：

  Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (3) and phenylboronic acid congeners gave the phenylpropenoid 2,3,4,6-tetra-O-acetyl-beta-D-glueopyranoside (4a-f) in good.yield. Among them, compounds 4a-c were converted to the naturally occurring phenylpropenoid beta-D-glucopyranoside analogues (1a-c). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.023
• 作为产物：
  描述：

  allyl β-D-glucopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 lithium acetate 、 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 4-cyanocinnamyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Simple preparation of phenylpropenoid β-d-glucopyranoside congeners by Mizoroki–Heck type reaction using organoboron reagents

  摘要：

  Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-beta-(D)-glucopyranoside (3) and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- beta-(D)-glucopyranosides (4a-m) in good yield. Among them, coupling products 4a-m were converted to not only the naturally occurring phenylpropenoid beta-(D)-glucopyranoside analogues (la-e) but also the unnaturally ones (If-m). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.08.043