(3R,4S)-trans-isoflavan-4-ol | 1021187-21-2

• 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: (3R,4S)-trans-isoflavan-4-ol
• 英文别名: trans-Isoflavanol-4；trans-Isoflavan-4-ol；(3R,4S)-isoflavan-4-ol；(3R,4S)-3-phenyl-3,4-dihydro-2H-chromen-4-ol
• CAS: 1021187-21-2
• 化学式: C₁₅H₁₄O₂
• 分子量: 226.275
• InChiKey: KKBIDVILXNDFLH-DZGCQCFKSA-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：

  大豆异黄酮 在 palladium on activated charcoal ammonium formate 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 (3R,4R)-cis-isoflavan-4-ol 、 trans-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol 、 (3R,4S)-trans-isoflavan-4-ol 、 cis-2,3-dihydro-3-phenyl-4H-benzopyran-4-ol
  参考文献：
  名称：

  Absolute configurations of isoflavan-4-ol stereoisomers

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2008.01.116

文献信息

• Production of isoflavone derivatives
  申请人：Heaton Andrew

  公开号：US20050143588A1

  公开（公告）日：2005-06-30

  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.

  描述了异黄酮氢化的方法，可以获得可操作数量的异黄烷-4-醇、异黄烯和异黄烷。在使用药用可接受的试剂和溶剂时，可以高纯度地获得异黄酮衍生物，并且产率接近定量。
• 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.
• US7906660B2
  申请人：——

  公开号：US7906660B2

  公开（公告）日：2011-03-15
• US8765420B2
  申请人：——

  公开号：US8765420B2

  公开（公告）日：2014-07-01
• 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.