2(S*)-<α(R*)-hydroxy-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 2(S*)-<α(R*)-hydroxy-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone
• 英文别名: (2R,3S,4S)-4-[(R)-1,3-benzodioxol-5-yl(hydroxy)methyl]-2-(3,4-dimethoxyphenyl)-5-oxooxolane-3-carboxylic acid
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: CAKQBMIYYMWHPO-VJANTYMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2(S*)-<α(R*)-hydroxy-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以96%的产率得到(1S*,2R*,5S*,6R*)-2-(3,4-dimethoxyphenyl)-6-<3,4-(methylenedioxy)phenyl>-4,8-dioxo-3,7-dioxabicyclo<3.3.0>octane
  参考文献：
  名称：

  First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

  摘要：

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.

  DOI：

  10.1021/jo961733y
• 作为产物：
  描述：

  Benzo[1,3]dioxol-5-yl-(tert-butyl-dimethyl-silanyloxy)-acetonitrile 在 咪唑 、 N-甲基吡咯烷酮 、 氟化铵 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢氟酸 、 四丁基氟化铵 、 sodium hexamethyldisilazane 、 乙酸酐 、 溶剂黄146 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.83h， 生成 2(S*)-<α(R*)-hydroxy-3,4-(methylenedioxy)benzyl>-3(S*)-carboxy-4(R*)-(3,4-dimethoxyphenyl)butyrolactone
  参考文献：
  名称：

  First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol

  摘要：

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.

  DOI：

  10.1021/jo961733y

文献信息

• The first synthesis of diaxial bislactone furofuran lignan
  作者：Shin-ichi Yoshida、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1016/0040-4039(95)01599-d

  日期：1995.11
• First Stereocontrolled Syntheses of Unsymmetrically Substituted Bislactone Lignans:  Stereocontrolled Syntheses of Four Possible Isomers of Methyl 4,8-Dioxoxanthoxylol
  作者：Shin-ichi Yoshida、Tsuyoshi Ogiku、Hiroshi Ohmizu、Tameo Iwasaki

  DOI：10.1021/jo961733y

  日期：1997.3.1

  An efficient method for stereocontrolled syntheses of the unsymmetrically substituted bislactone subgroup of the furofuran lignan has been developed based on a stereoselective aldol reaction of the acid anhydride 8 or 9 and an aromatic aldehyde employing methyl 4,8-dioxoxanthoxylol (1a), 4,8-dioxofargesin (1b), methyl 4,8-dioxopiperitol (2a) and their isomer 3a as the representative examples of the axial-equatorial 1, diequatorial 2, and diaxial 3 types of this series.