cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol | 1481-96-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol
• 英文别名: cis-isoflavan-4-ol；cis(β)-4-Hydroxy-isoflavan；cis-3-Phenyl-chroman-4-ol；(3S,4S)-3-phenyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 1481-96-5；6212-70-0；20986-77-0
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: KKBIDVILXNDFLH-UKRRQHHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 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

• 作为产物：
  描述：

  3-碘代色酮,97 在 四(三苯基膦)钯 、 C₈₄H₈₀Cl₄N₂O₂P₄Ru₃ 、 氢气 、 sodium carbonate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 、 甲苯 为溶剂， 20.0~110.0 ℃ 、6.0 MPa 条件下， 反应 48.0h， 生成 cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol
  参考文献：
  名称：

  RuPHOX-Ru 催化 3-取代色酮的不对称级联氢化反应合成相应的手性色醇

  摘要：

  在温和的反应条件下实现了高效的 RuPHOX−Ru 催化 3-取代色酮的不对称级联氢化，以高产率提供相应的手性 3-取代色酮，并具有优异的对映和非对映选择性。在随后的C=O双键氢化过程中发生动态动力学拆分过程，这是不对称级联氢化的高性能的原因。

  DOI：

  10.1002/chem.202400978

文献信息

• Formation of hydridocobalt(iii) phthalocyanine by reaction of cobalt(ii) phthalocyanines with sodium borohydride and its reactions with antioxidant isoflavones
  作者：Poonam、Pratibha Kumari、Ritika Nagpal、Shive M. S. Chauhan

  DOI：10.1039/c1nj20582j

  日期：——

  The reduction of substituted isoflavones with sodium borohydride catalyzed by cobalt(II) phthalocyanines has been achieved efficiently to yield cis- and trans-isoflavan-4-ols under mild conditions via the formation of a hydridocobalt(III) phthalocyanine intermediate. The hydroxy isoflavones react with sodium borohydride to form the corresponding phenolate moiety and thereby prevent the formation of

  取代异黄酮与 硼氢化钠通过形成氢化钴（III）酞菁中间体，在温和条件下已有效地实现了钴（II）酞菁催化，可生成顺式和反式异黄烷-4-醇。羟基异黄酮与硼氢化钠形成相应的酚盐部分，从而防止形成氢化钴（III）酞菁中间体，从而抑制其还原为相应的异黄烷-4-醇。
• [EN] PRODUCTION OF ISOFLAVONE DERIVATIVES<br/>[FR] DERIVES D'ISOFLAVONE
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2000049009A1

  公开（公告）日：2000-08-24

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了一些对异黄酮进行氢化的方法，可以获得可用量的异黄酮-4-醇、异黄酮-3-烯和异黄酮。在使用药用可接受试剂和溶剂的同时，可以高纯度地获得异黄酮衍生物，并且接近定量收率。
• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20060217564A1

  公开（公告）日：2006-09-28

  Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

  本文描述了用于对异黄酮进行加氢的方法，该方法可以获得可操作量的异黄酮-4-醇，异黄酮-3-烯和异黄酮。在使用药用可接受的试剂和溶剂的情况下，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• Experimental and DFT ¹H NMR Study of Conformational Equilibria in <i>trans</i>-4‘,7-Dihydroxyisoflavan-4-ol and <i>trans</i>-Isoflavan-4-ol
  作者：Kalevi Pihlaja、Petri Tähtinen、Karel D. Klika、Tuija Jokela、Auli Salakka、Kristiina Wähälä

  DOI：10.1021/jo0301200

  日期：2003.9.1

  The solution-state conformational equilibria of trans-4',7-dihydroxyisoflavan-4-ol (1) and trans-isoflavan-4-ol (2) were assessed based on the temperature dependence of their vicinal coupling constants J(H-2alpha,H-3) and J(H-3,H-4) in comparison to values calculated with density functional theory (DFT) methods at the B3LYP/cc-pVTZ//B3LYP/6-31G(d,p) level of theory. For each half-chair conformer, several rotamers with respect to the C-4 hydroxyl and C-3 phenyl were calculated and the overall diequatorial-to-diaxial ratio at 298 K was assessed as 66:34 for 1 and 73:27 for 2. The syntheses of 1 and 2 are described.
• Absolute configurations of isoflavan-4-ol stereoisomers
  作者：Dongho Won、Bok-Kyu Shin、Suil Kang、Hor-Gil Hur、Mihyang Kim、Jaehong Han

  DOI：10.1016/j.bmcl.2008.01.116

  日期：2008.3

  Isoflavan-4-ol has been synthesized quantitatively from the reduction of isoflavone in the presence of Pd/C and ammonium formate under N(2) atmosphere. Isolation of cis- and trans-isomers was achieved by. ash column chromatography and each enantiomer was separated by Sumi-Chiral column chromatography. Absolute configurations of four stereoisomers were determined by circular dichroism spectroscopy. (C) 2008 Elsevier Ltd. All rights reserved.