trans-flavan-4-ol tosylate | 104819-73-0

• 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: trans-flavan-4-ol tosylate
• CAS: 104819-73-0
• 化学式: C₂₂H₂₀O₄S
• 分子量: 380.464
• InChiKey: PKOYXLJSJWMIQQ-YADHBBJMSA-N

物化性质

• 沸点：
  542.9±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.97
• 重原子数：
  27.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  trans-flavan-4-ol tosylate 在 葡萄糖 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 73.0h， 生成 flavan-4α-ol
  参考文献：
  名称：

  Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures

  摘要：

  This research investigated stereochemistry of reduction of racemic flavanone and a concurrent competitive process of oxidation, taking place in cultures of live yeast strains. The results obtained gave us information about capability of tested biocatalysts for enantioselective (with respect to both substrate and product) reduction of flavanone and for enantioselective oxidation of the resulting cis- and trans-flavan-4-ols. As a result of our experiments we obtained (2S,4S)-cis-flavan-4-ol with 43% of conversion and 96% of enantiomeric excess, and (2R,4S)-trans-flavan-4-ol with 41% of conversion and ee > 99% in the culture of Rhodotorula rubra; (2S,4S)-cis-flavan-4-ol (43%, ee = 96%) along with (2R,4R)-cis-flavan-4-ol (44%, ee = 61%) in the culture of Zygosaccharomyces bailii KCh 907. Additionally, some of the tested strains demonstrated an excellent capability for enantioselective oxidation of (+/-)-cis-flavan-4-ol and (+/-)-trans-flavan-4-ol, obtained by chemical synthesis. A one-day biotransformation in the culture of Candida parapsilosis KCh 909 afforded (S)-flavanone (ee = 93%) as 49% of the reaction mixture and 49% of unreacted (2R,4R)-cis-flavan-4-ol with ee = 97%. Racemic trans-flavan-4-ol was effectively oxidized in the culture of Yarrowia lipolytica KCh 71 - after a three-day biotransformation the reaction mixture contained 52% of (R)-flavanone (ee = 85%) and 48% of (2R,45)-trans-flavan-4-ol with a high enantiomeric excess (ee = 93%). (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.006
• 作为产物：
  描述：

  黄烷酮 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 trans-flavan-4-ol tosylate
  参考文献：
  名称：

  Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures

  摘要：

  This research investigated stereochemistry of reduction of racemic flavanone and a concurrent competitive process of oxidation, taking place in cultures of live yeast strains. The results obtained gave us information about capability of tested biocatalysts for enantioselective (with respect to both substrate and product) reduction of flavanone and for enantioselective oxidation of the resulting cis- and trans-flavan-4-ols. As a result of our experiments we obtained (2S,4S)-cis-flavan-4-ol with 43% of conversion and 96% of enantiomeric excess, and (2R,4S)-trans-flavan-4-ol with 41% of conversion and ee > 99% in the culture of Rhodotorula rubra; (2S,4S)-cis-flavan-4-ol (43%, ee = 96%) along with (2R,4R)-cis-flavan-4-ol (44%, ee = 61%) in the culture of Zygosaccharomyces bailii KCh 907. Additionally, some of the tested strains demonstrated an excellent capability for enantioselective oxidation of (+/-)-cis-flavan-4-ol and (+/-)-trans-flavan-4-ol, obtained by chemical synthesis. A one-day biotransformation in the culture of Candida parapsilosis KCh 909 afforded (S)-flavanone (ee = 93%) as 49% of the reaction mixture and 49% of unreacted (2R,4R)-cis-flavan-4-ol with ee = 97%. Racemic trans-flavan-4-ol was effectively oxidized in the culture of Yarrowia lipolytica KCh 71 - after a three-day biotransformation the reaction mixture contained 52% of (R)-flavanone (ee = 85%) and 48% of (2R,45)-trans-flavan-4-ol with a high enantiomeric excess (ee = 93%). (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.08.006

文献信息

• Stereoselectivity at benzylic carbon
  作者：A. Hirwe、K.G. Marathe、S.S. Mohorkar、K. Ramdas、C.B. Singh

  DOI：10.1016/s0040-4020(01)87374-9

  日期：1986.1

  Some reactions of 4-substituted flavans have been studied. 4-Chloro/bromo derivatives react under neutral conditions with phthalimide and acetonitrile leading to displacement or axial halogen by nitrogen with inversion. In contrast, irrespective of the stereochemistry, 4-hydroxy-derivatives react under acidic or basic conditions leading to axial attack by the nudeophiles SOCl2, PCl3, PCl5, SOBr2, PBr3

  已经研究了4-取代的黄烷的一些反应。4-氯/溴衍生物在中性条件下与邻苯二甲酰亚胺和乙腈反应，导致氮转化而取代或轴向被卤素取代。相反，无论立体化学如何，4-羟基衍生物在酸性或碱性条件下反应都会导致亲核体SOCl 2，PCl 3，PCl 5，SOBr 2，PBr 3，PBr 5，乙腈和水引起轴向攻击。苄基碳正离子的中间形成。