(2R,4S)-trans-flavan-4-ol | 27439-08-3

• 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: (2R,4S)-trans-flavan-4-ol
• 英文别名: (2R,4S)-2-phenyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 27439-08-3
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: YTMFRMLVZQOBDR-DZGCQCFKSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  383.2±42.0 °C(Predicted)
• 密度：
  1.200±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,4S)-trans-flavan-4-ol 、 重铬酸钠 以76%的产率得到
  参考文献：
  名称：

  RAKOSI M.; TOEKES A. L.; BOGNAR R., ACTA CHIM. ACAD. SCI. HUNG. , 1975, 87, NO 2, 161-164

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,4S)-(-)-4-aminoflavan hydrochloride 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 以30%的产率得到(2R,4S)-trans-flavan-4-ol
  参考文献：
  名称：

  Toekes, Adrienne L., Liebigs Annalen der Chemie, 1989, p. 89 - 90

  摘要：

  DOI：

文献信息

• Ruthenium-NHC-Catalyzed Asymmetric Hydrogenation of Flavones and Chromones: General Access to Enantiomerically Enriched Flavanones, Flavanols, Chromanones, and Chromanols
  作者：Dongbing Zhao、Bernhard Beiring、Frank Glorius

  DOI：10.1002/anie.201302573

  日期：2013.8.5

  Two to four! Readily available flavones and chromones were efficiently converted into four valuable chiral classes of O‐heterocycles—flavanones, chromanones, flavanols, and chromanols—by means of an enantioselective Ru/NHC‐catalyzed hydrogenation process (see scheme; NHC=N‐heterocyclic carbene, PCC=pyridinium chlorochromate).

  二到四！现成的黄酮和色酮通过对映选择性Ru / NHC催化的加氢过程有效地转化为四种有价值的O-杂环手性类别-黄酮，色酮，黄烷醇和色醇-参见表; NHC = N-杂环卡宾， PCC =吡啶鎓氯铬酸盐）。
• Stereoselective reduction of flavanones by marine-derived fungi
  作者：Iara L. de Matos、Willian G. Birolli、Darlisson de A. Santos、Marcia Nitschke、André Luiz M. Porto

  DOI：10.1016/j.mcat.2021.111734

  日期：2021.8

  enantiomeric excesses (ee) of both cis- and trans-diastereoisomers (up to >99% ee). Ten strains were screened for reduction of flavanone 2a in liquid medium and in phosphate buffer solution. The most selective strains Cladosporium sp. CBMAI 1237 and Acremonium sp. CBMAI1676 were employed for reduction of flavanones 2a-g. The fungus Cladosporium sp. CBMAI 1237 presented yields of 72–87% with 0–64% ee cis and

  生物转化是一种具有巨大潜力的替代方法，可以改变天然和合成类黄酮的结构。因此，描述了使用海洋来源的真菌对合成卤化黄烷酮进行生物还原，旨在合成具有高对映体过量 ( ee ) 的顺式和反式非对映异构体 (高达 >99% ee ) 的黄烷-4-醇3a-g）。在液体培养基和磷酸盐缓冲溶液中筛选了 10 株减少黄烷酮2a 的菌株。最具选择性的菌株Cladosporium sp。CBMAI 1237 和枝顶孢属。CBMAI1676 用于还原黄烷酮2a-g. 真菌Cladosporium sp。CBMAI 1237呈现的72-87％的收率与0-64％ee值顺式和0-30％的EE的反式与非对映异构比（博士从52:48至64:36（）顺式：反式）。而枝顶孢属。CBMAI 1676导致31％的产率与77-99％ee值的的顺式和95-99％ee值的的反式-非对映体3A-G与博士从54:46至96：4（顺式：反式）。据我们所知，这是溴化
• Ruthenium-Catalyzed Dynamic Kinetic Resolution Asymmetric Transfer Hydrogenation of β-Chromanones by an Elimination-Induced Racemization Mechanism
  作者：Eric R. Ashley、Edward C. Sherer、Barbara Pio、Robert K. Orr、Rebecca T. Ruck

  DOI：10.1021/acscatal.6b03191

  日期：2017.2.3

  compounds is an important goal. Ruthenium-catalyzed asymmetric transfer hydrogenation under strongly basic conditions has been found to induce dynamic kinetic resolution of β-substituted chromanones, producing valuable chromanols in high yields and with high levels of stereocontrol. The reaction proceeds by base-catalyzed racemization of the β-stereocenter through a conjugate elimination/conjugate

  手性苯并二氢吡喃衍生物是天然和合成生物活性分子中的重要药效团。发现用于合成这些化合物的催化不对称方法是重要的目标。已发现在强碱性条件下钌催化的不对称转移氢化可诱导β-取代的苯并二氢吡喃酮的动态动力学拆分，从而以高收率和高水平的立体控制产生有价值的苯并二氢吡喃醇。反应是通过共轭消除/共轭加成途径，与高度选择性的酮转移氢化步骤相结合，通过β-立体中心的碱催化外消旋而进行的。催化剂，底物的计算分析
• Enantioselective reduction of flavanone and oxidation of cis- and trans-flavan-4-ol by selected yeast cultures
  作者：Tomasz Janeczko、Monika Dymarska、Monika Siepka、Radosław Gniłka、Agnieszka Leśniak、Jarosław Popłoński、Edyta Kostrzewa-Susłow

  DOI：10.1016/j.molcatb.2014.08.006

  日期：2014.11

  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.
• TOKES, ADRIENNE L., LIEBIGS ANN. CHEM.,(1989) N, C. 89-90
  作者：TOKES, ADRIENNE L.

  DOI：——

  日期：——