(2S,3S)-1-methoxyspirobrassinol (1R,2S,5R)-menthyl ether | 960207-26-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,3S)-1-methoxyspirobrassinol (1R,2S,5R)-menthyl ether
• 英文别名: (2S,3S)-1-methoxy-2-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-2'-methylsulfanylspiro[2H-indole-3,5'-4H-1,3-thiazole]
• CAS: 960207-26-5
• 化学式: C₂₂H₃₂N₂O₂S₂
• 分子量: 420.64
• InChiKey: ZGQZVSBLIFYSPN-CSRWUHQLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  84.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-1-methoxyspirobrassinol (1R,2S,5R)-menthyl ether 在 magnesium sulfate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到(S)-(-)-1-methoxyspirobrassinin
  参考文献：
  名称：

  Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues

  摘要：

  The stereoselective synthesis of the spiroindoline phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(-)-enantiomer were achieved by the bromine-induced spirocyclization of 1-methoxybrassinin using chiral auxiliaries (+)- and (-)-menthol, followed by oxidation of the obtained menthyl ethers. The TFA-catalyzed methanolysis of chiral 1-methoxyspirobrassinol menthyl ethers provided (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and its other three unnatural stereoisomers. The enantiomers of the 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether were prepared by the TFA-catalyzed replacement of the chiral alkoxy group with an amine. The synthesized compounds were tested in vitro on cancer cell lines and examined with enantiopure 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether, which showed in most cases, lower activity than the corresponding racemates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.07.006
• 作为产物：
  描述：

  L-薄荷醇 、 甲基[(1-甲氧基-1H-吲哚-3-基)甲基]二硫代氨基甲酸酯 在 溴 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以40%的产率得到(2S,3S)-1-methoxyspirobrassinol (1R,2S,5R)-menthyl ether
  参考文献：
  名称：

  Stereoselective synthesis of 1-methoxyspiroindoline phytoalexins and their amino analogues

  摘要：

  The stereoselective synthesis of the spiroindoline phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(-)-enantiomer were achieved by the bromine-induced spirocyclization of 1-methoxybrassinin using chiral auxiliaries (+)- and (-)-menthol, followed by oxidation of the obtained menthyl ethers. The TFA-catalyzed methanolysis of chiral 1-methoxyspirobrassinol menthyl ethers provided (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether and its other three unnatural stereoisomers. The enantiomers of the 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether were prepared by the TFA-catalyzed replacement of the chiral alkoxy group with an amine. The synthesized compounds were tested in vitro on cancer cell lines and examined with enantiopure 2-amino analogues of the indole phytoalexin (2R,3R)-(-)-1-methoxyspirobrassinol methyl ether, which showed in most cases, lower activity than the corresponding racemates. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.07.006

文献信息

• Stereoselective synthesis of (R)-(+)-1-methoxyspirobrassinin, (2R,3R)-(−)-1-methoxyspirobrassinol methyl ether and their enantiomers or diastereoisomers
  作者：Zuzana Čurillová、Peter Kutschy、Mariana Budovská、Atsufumi Nakahashi、Kenji Monde

  DOI：10.1016/j.tetlet.2007.09.080

  日期：2007.11

  phytoalexin (R)-(+)-1-methoxyspirobrassinin and its unnatural (S)-(−)-enantiomer was achieved by spirocyclization of 1-methoxybrassinin in the presence of (+)- and (−)-menthol and subsequent oxidation of the obtained menthyl ethers. Methanolysis of menthyl ethers in the presence of TFA afforded (2R,3R)-(−)-1-methoxyspirobrassinol methyl ether as well its unnatural (2S,3S)-, (2R,3S)-, and (2S,3R)-isomers

  （十字花科吲哚植物抗毒素的立体选择性合成- [R（+） - - ）1-methoxyspirobrassinin和其非天然（小号） - （ - ） -对映异构体通过在（+）的存在下1- methoxybrassinin的螺环化来实现-和（ - ） -薄荷醇和随后氧化得到的薄荷醚。在TFA存在下，对薄荷基醚进行甲醇分解，得到（2 R，3 R）-（-）-1-甲氧基螺spir菜油醇甲基醚及其非天然的（2 S，3 S）-，（2 R，3 S）-和（2 S，3 R）-异构体。