(+)-(R)-5-hydroxy-7-methoxy-8-methylflavanone | 249931-52-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (+)-(R)-5-hydroxy-7-methoxy-8-methylflavanone
• 英文别名: (2R)-5-hydroxy-7-methoxy-8-methyl-2-phenyl-2,3-dihydrochromen-4-one
• CAS: 249931-52-0
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: SNHQMOIKQSCRFM-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (+)-(R)-5-hydroxy-7-methoxy-8-methylflavanone 在 盐酸 、 溶剂黄146 作用下， 反应 4.0h， 以71%的产率得到(+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone
  参考文献：
  名称：

  Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone

  摘要：

  The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of beta-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetrachlorocuprate was shown to be a very efficient catalyst for the conjugate addition reaction of phenyl magnesium bromide to the alpha,beta-unsaturated sulfoxide 12. The instability of the obtained adducts 10 represents a limitation in terms of yield. It was confirmed that the natural flavanone leridol does not possess the structure of title compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00266-9
• 作为产物：
  描述：

  (-)-(R_S)-1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-2-(p-tolylsulfinyl)ethanone 在 aluminum amalgam 、 三氯化铝 、 dilithium tetrachlorocuprate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.58h， 生成 (+)-(R)-5-hydroxy-7-methoxy-8-methylflavanone
  参考文献：
  名称：

  Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone

  摘要：

  The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of beta-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetrachlorocuprate was shown to be a very efficient catalyst for the conjugate addition reaction of phenyl magnesium bromide to the alpha,beta-unsaturated sulfoxide 12. The instability of the obtained adducts 10 represents a limitation in terms of yield. It was confirmed that the natural flavanone leridol does not possess the structure of title compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00266-9

文献信息

• Synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone
  作者：Guy Solladié、Nicolai Gehrold、Jean Maignan

  DOI：10.1016/s0957-4166(99)00266-9

  日期：1999.7

  The synthesis of (+)-(R)-5-hydroxy-6-hydroxymethyl-7-methoxy-8-methylflavanone is described. A new chromylation method of beta-ketosulfoxide 9 leading to the Michael acceptor 12 has been developed. Dilithium tetrachlorocuprate was shown to be a very efficient catalyst for the conjugate addition reaction of phenyl magnesium bromide to the alpha,beta-unsaturated sulfoxide 12. The instability of the obtained adducts 10 represents a limitation in terms of yield. It was confirmed that the natural flavanone leridol does not possess the structure of title compound 1. (C) 1999 Elsevier Science Ltd. All rights reserved.