trans-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: trans-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol
• 英文别名: trans-isoflavan-4-ol；trans(α)-4-Hydroxy-isoflavan；trans-3-t-Butyl-chroman-4-ol；trans-3-Phenyl-chroman-4-ol；trans-4-Hydroxy-isoflavan；(3S,4R)-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-HIFRSBDPSA-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：

  异黄烷酮 在 lithium tri-t-butoxyaluminum hydride 作用下， 以 四氢呋喃 为溶剂， 生成 trans-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol 、 cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol
  参考文献：
  名称：

  Experimental and DFT ¹H NMR Study of Conformational Equilibria in trans-4‘,7-Dihydroxyisoflavan-4-ol and trans-Isoflavan-4-ol

  摘要：

  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.

  DOI：

  10.1021/jo0301200

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。
• 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.
• NOVEL METHOD FOR PREPARING PTEROCARPAN
  申请人：Hur Hor-Gil

  公开号：US20130130332A1

  公开（公告）日：2013-05-23

  The present invention relates to a novel method for preparing pterocarpan from isoflavan-4-ol. With the use of the method of the present invention, the absolute configuration of C3 and C4 positions on the B-ring of isoflavan-4-ols is maintained identically also in pterocarpans, and thus, enantiopure pterocarpans can be efficiently prepared.
• US8765420B2
  申请人：——

  公开号：US8765420B2

  公开（公告）日：2014-07-01
• 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.