1-C-(β-D-glucopyranosyl)-3-phenylacetone | 250590-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-C-(β-D-glucopyranosyl)-3-phenylacetone
• 英文别名: 1-phenyl-3-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]propan-2-one
• CAS: 250590-59-1
• 化学式: C₁₅H₂₀O₆
• 分子量: 296.32
• InChiKey: ONPCEOACCLEWER-XPABHHOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-C-(β-D-glucopyranosyl)-3-phenylacetone 在 hydroxylamine-O-sulfonic acid 、 potassium hydrogencarbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 以100%的产率得到1-C-β-D-glucopyranosyl-3-phenylacetone oxime O-sulfonate potassium salt
  参考文献：
  名称：

  Synthetic Approaches to C-Glucosinolates

  摘要：

  In these pages, short and efficient synthetic approaches to C-analogs of glucosinolates are described. Starting from D-glucose, C-glucotropaeolin (6) and C-glucocapparin (11) were synthesized in three steps. Preliminary enzymatic assays involving sulfatase and myrosinase have been performed. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00153-8
• 作为产物：
  描述：

  苯乙酸甲酯 在 水 、 sodium methylate 、 溶剂黄146 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 46.5h， 生成 1-C-(β-D-glucopyranosyl)-3-phenylacetone
  参考文献：
  名称：

  Synthetic Approaches to C-Glucosinolates

  摘要：

  In these pages, short and efficient synthetic approaches to C-analogs of glucosinolates are described. Starting from D-glucose, C-glucotropaeolin (6) and C-glucocapparin (11) were synthesized in three steps. Preliminary enzymatic assays involving sulfatase and myrosinase have been performed. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00153-8

文献信息

• The first synthesis of C-glucotropaeolin
  作者：V. Aucagne、D. Gueyrard、A. Tatibouët、S. Cottaz、H. Driguez、M. Lafosse、P. Rollin

  DOI：10.1016/s0040-4039(99)01416-1

  日期：1999.10

  Starting from tetra-O-benzyl-D-glucose (2), the first synthesis of a C-analogue 7 of glucotropaeolin, the major glucosinolate of the genus Nasturtium was performed. Compound 7 constitutes a potential non-hydrolyzable inhibitor of the enzyme myrosinase. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.
• Synthetic Approaches to C-Glucosinolates
  作者：Vincent Aucagne、David Gueyrard、Arnaud Tatibouët、Alain Quinsac、Patrick Rollin

  DOI：10.1016/s0040-4020(00)00153-8

  日期：2000.4

  In these pages, short and efficient synthetic approaches to C-analogs of glucosinolates are described. Starting from D-glucose, C-glucotropaeolin (6) and C-glucocapparin (11) were synthesized in three steps. Preliminary enzymatic assays involving sulfatase and myrosinase have been performed. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.