3-(naphthalen-2-yl)allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 869729-00-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-(naphthalen-2-yl)allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 869729-00-0
• 化学式: C₂₇H₃₀O₁₀
• 分子量: 514.529
• InChiKey: MCVWTWQCIIIHLF-BKSMTMGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  123.66
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  3-(naphthalen-2-yl)allyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.5h， 以73%的产率得到3-naphthalen-2-ylallyl 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
• 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 3-(naphthalen-2-yl)allyl 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