(3S,5S)-[6]-gingerdiol

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3S,5S)-[6]-gingerdiol
• 英文别名: (6S,8S)-6-gingerdiol；(3S,5S)-1-(4-hydroxy-3-methoxyphenyl)decane-3,5-diol
• 化学式: C₁₇H₂₈O₄
• 分子量: 296.407
• InChiKey: QYXKQNMJTHPKBP-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,5S)-[6]-gingerdiol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以94%的产率得到4-(2-((4S,6S)-2,2-dimethyl-6-pentyl-1,3-dioxan-4-yl)ethyl)-2-methoxyphenol
  参考文献：
  名称：

  Synthesis of gingerol and diarylheptanoids

  摘要：

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.11.010
• 作为产物：
  描述：

  6-姜酚 在 glucose dehydrogenase 、 葡萄糖 、 烟酰胺腺嘌呤双核苷酸磷酸盐 、 alcohol dehydrogenase evo-1.1.250 作用下， 以90%的产率得到(3S,5S)-[6]-gingerdiol
  参考文献：
  名称：

  立体选择性生物催化还原工业废物中回收的生姜活性成分

  摘要：

  生姜活性成分已成功从发酵生姜的工业废生物质中回收，并通过立体选择性生物催化还原转化为相应的二醇和醇。

  DOI：

  10.1002/cbic.202200105

文献信息

• A new method for the demetallation of tricarbonyliron diene complexes by total hydrogenation with Raney nickel. Application to a very short synthesis of (+)-[6]-gingerdiol
  作者：Michel Franck-Neumann、Philippe Geoffroy、Paul Bissinger、Sylvie Adelaide

  DOI：10.1016/s0040-4039(01)01263-1

  日期：2001.9

  by treatment with freshly prepared Raney nickel. The ligands which are totally hydrogenated during the decomplexation are easily isolated in high yields, without racemization, if chiral. A very short and efficient synthesis of (+)-(3R,5S)-[6]-gingerdiol, based on this novel decomplexation procedure, which also allows the synthesis of the other diastereomers/enantiomers, is described.

  通过用新鲜制备的阮内镍处理，可以快速实现三羰基铁二烯配合物的脱金属。如果手性的话，很容易以高收率分离出在解配合过程中完全氢化的配体，而没有外消旋作用。描述了基于这种新颖的分解过程的非常短而有效的合成（+）-（3 R，5 S）-[6]-姜二醇，该合成方法还允许合成其他非对映异构体/对映异构体。
• Gingerdiol related compounds from the rhizomes of Zingiber officinale
  作者：Hiroe Kikuzaki、Saiu-Mei Tsai、Nobuji Nakatani

  DOI：10.1016/0031-9422(92)83147-q

  日期：1992.5

  [6]-Gingerdiol and four analogues, (3R,5S)-5-acetoxy-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane, (3R,5S)-3-acetoxy-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane,(3R,5S)-3,5-diacetoxy-1-(4-hydroxy-3-methoxyphenyl)decane and (3R,5S)-3,5-diacetoxy-1-(3,4-dimethoxyphenyl)decane, were isolated from the rhizomes of Zingiber officinale. Their structures were established by chemical and spectroscopic evidence.
• Synthesis of gingerol and diarylheptanoids
  作者：Gowravaram Sabitha、Chitti Srinivas、Teega Rammohan Reddy、Kurra Yadagiri、Jhillu Singh Yadav

  DOI：10.1016/j.tetasy.2011.11.010

  日期：2011.12

  The synthesis of gingerol 1 and related compounds 2-5 along with diarylheptanoids 6-8 has been accomplished using a Keck allylation, Crimmins' aldol reaction, aldehyde coupling with acetylene, and chelation controlled reductions as the key reactions. The absolute configuration of these molecules was confirmed by preparing their acetonide derivatives and by comparison of the NMR data with natural compounds. (C) 2011 Elsevier Ltd. All rights reserved.
• Stereoselective Biocatalyzed Reductions of Ginger Active Components Recovered from Industrial Wastes
  作者：Rita Nasti、Ivan Bassanini、Erica Elisa Ferrandi、Federica Linguardo、Susanna Bertuletti、Marta Vanoni、Sergio Riva、Luisella Verotta、Daniela Monti

  DOI：10.1002/cbic.202200105

  日期：2022.4.20

  Ginger active constituents have been successfully recovered from industrial waste biomasses of fermented ginger and converted into the corresponding diols and alcohols by stereoselective biocatalyzed reductions.

  生姜活性成分已成功从发酵生姜的工业废生物质中回收，并通过立体选择性生物催化还原转化为相应的二醇和醇。