flavan-4α-ol

• 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: flavan-4α-ol
• 英文别名: (±)-trans-flavan-4-ol；(2S,4R)-2-phenyl-3,4-dihydro-2H-chromen-4-ol
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: YTMFRMLVZQOBDR-HIFRSBDPSA-N

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：

  flavan-4α-ol 在 氯化亚砜 作用下， 以 吡啶 、 水 为溶剂， 反应 0.17h， 生成 2-phenylchromene
  参考文献：
  名称：

  在苄基碳上的立体选择性：类黄酮-V 1。反式4-乙酰氨基黄酮的合成

  摘要：

  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。

  DOI：

  10.1016/s0040-4020(01)87374-9
• 作为产物：
  描述：

  黄烷酮 在 吡啶 、 sodium tetrahydroborate 、 水 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 26.0h， 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

文献信息

• Approaches to 2-substituted chroman-4-ones: synthesis of (−)-pinostrobin
  作者：Kevin J Hodgetts

  DOI：10.1016/s0040-4039(01)00567-6

  日期：2001.5

  Two approaches to optically active 2-substituted chroman-4-ones are described. The first utilized the oxidation of a preformed chroman ring and the second an intramolecular Mitsunobu cyclization. The methodology was applied to the synthesis of the biologically active natural product (−)-pinostrobin (18).

  描述了两种光学活性的2-取代的苯并吡喃-4-酮的方法。第一种利用预先形成的苯并二氢吡喃环的氧化，第二种利用分子内光延环化。该方法被应用于生物活性天然产物（-）-pinostrobin（18）的合成。
• 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
• Regioselective and chemoselective biotransformation of 2′-hydroxychalcone derivatives by marine-derived fungi
  作者：Iara Lisboa de Matos、Marcia Nitschke、André Luiz Meleiro Porto

  DOI：10.1080/10242422.2021.1956909

  日期：2023.1.2

  biotransformation of the 2′-hydroxychalcone 1a. The main products obtained were from hydrogenation, hydroxylation, and cyclization reactions. Penicillium raistrickii CBMAI 931 catalyzed the chemoselective reduction of 1a to produce 2′-hydroxydihydrochalcone 2a (72%) in 7 days of incubation in phosphate buffer (pH 7). Aspergillus sydowii CBMAI 935 promoted the hydroxylation of 1a to yield 2′,4-dihydroxy-dihydrochalcone

  摘要 八种真菌菌株（Penicillium raistrickii CBMAI 931、Cladosporium sp. CBMAI 1237、Aspergillus sydowii CBMAI 935、Penicillium oxalicum CBMAI 1996、Penicillium citrinum CBMAI 1186、Mucor racemosus CBMAI 847、Westerdykella sp. CBMAI 1679 和 Asperdykella sp. CBMAI 1679 和Aspergillus biorottransformation9 BMAI） 2'-羟基查尔酮1a。获得的主要产物来自氢化、羟基化和环化反应。雷氏青霉CBMAI 931 催化1a化学选择性还原生成 2'-羟基二氢查尔酮2a (72%) 在磷酸盐缓冲液 (pH 7) 中孵育 7 天。Aspergillus
• Bateman, Graham; Brown, Ben R.; Campbell, John B., Journal of the Chemical Society. Perkin transactions I, 1983, # 12, p. 2903 - 2912
  作者：Bateman, Graham、Brown, Ben R.、Campbell, John B.、Cotton, Charles A.、Johnson, Philip、et al.

  DOI：——

  日期：——