(6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan | 108335-31-5

• 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: (6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan
• 英文别名: (6aR,11aR)-6a,11a-Dihydro-3,9-dimethoxy-6H-benzofuro[3,2-c][1]benzopyran-8-ol；(6aR,11aR)-3,9-dimethoxy-6a,11a-dihydro-6H-[1]benzofuro[3,2-c]chromen-8-ol
• CAS: 108335-31-5
• 化学式: C₁₇H₁₆O₅
• 分子量: 300.311
• InChiKey: KIKDCPYSYOMXEJ-SJCJKPOMSA-N

物化性质

• 沸点：
  439.8±45.0 °C(Predicted)
• 密度：
  1.312±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (6aR,11aR)-8-hydroxy-3,9-dimethoxypterocarpan 生成 (6aR,11aR)-8-acetoxy-3,9-dimethoxypterocarpan
  参考文献：
  名称：

  来自紫檀属的类黄酮类似物

  摘要：

  摘要 从P. soyauxii 的心材中分离到了两种新型翼果木，8-羟基-3,9-二甲氧基-和3,8-二羟基-9-甲氧基翼果木以及一种新的檀香类似物。这些伴随着几种已知的紫檀、异黄烷、异黄酮和反式紫檀芪。从 P. marsupium 的心材中获得了 8-C-β-d-吡喃葡萄糖基-3,7,4'-三羟基-和 -3,7,3',4'-四羟基黄酮，代表第一个 5-脱氧 CC -偶联的黄酮醇糖苷，和罕见的 3'-C-β-d-吡喃葡萄糖基-α-羟基二氢查尔酮，它们的结构是通过高分辨率 NMR 技术确定的。

  DOI：

  10.1016/s0031-9422(00)81448-x
• 作为产物：
  描述：

  (1R,10S,11R,16S)-5,14-dimethoxy-8-oxatetracyclo[8.6.0.02,7.011,16]hexadeca-2(7),3,5,13-tetraene-12,15-dione 、 对甲苯磺酸 以80%的产率得到
  参考文献：
  名称：

  ENGLER, THOMAS A.;REDDY, JAYACHANDRA P.;COMBRINK, KEITH D.;VANDER, VELDE +, J. ORG. CHEM., 55,(1990) N, C. 1248-1254

  摘要：

  DOI：

文献信息

• Engler, Thomas A.; Letavic, Michael A.; Reddy, Jayachandra P., Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5068 - 5070
  作者：Engler, Thomas A.、Letavic, Michael A.、Reddy, Jayachandra P.

  DOI：——

  日期：——
• Asymmetric Reactions of 2-Methoxy-1,4-benzoquinones with Styrenyl Systems:  Enantioselective Syntheses of 8-Aryl-3-methoxybicyclo[4.2.0]oct-3-en-2,5-diones, 7-Aryl-3-hydroxybicyclo[3.2.1]oct-3-en-2,8-diones, 2-Aryl-6-methoxy-2,3-dihydrobenzofuran-5-ols, and Pterocarpans
  作者：Thomas A. Engler、Michael A. Letavic、Rajesh Iyengar、Kenneth O. LaTessa、Jayachandra P. Reddy

  DOI：10.1021/jo982164s

  日期：1999.4.1

  Reactions of 2-methoxy-1,4-benzoquinones 2 and 3 with (E)-propenylbenzenes 1 promoted at -78 degrees C by Ti(IV)-TADDOLates prepared from diol-(+)- 4 afford (1R,6R,7R,8R)-8-aryl-3-methoxy-7methylbicyclo[4.2.0]oct-3-en-2,5-diones 5/8 or (1R,5R,6R,7R)-7-aryl-3-hydroxy-6-methylbicyclo-3-en-2,8-diones 7/10 in good yield and high ee. (2S,3S)-2-Aryl-6-methoxy-3-methyl-2,3-dihydrobenzofuran-5-ols 6/9 are also found, but in slightly lower ee. Cyclobutanes 5/8 cleanly and efficiently rearrange to the dihydrobenzofurans 6/9 without loss of enantiomeric purity upon treatment with the Ti-TADDOLates at higher temperatures. Reactions of (Z)-propenylbenzene 17 and of indene with 2 and 3 give products in moderate enantiomeric purity. Products obtained from reactions of 1-anisylcycloalkenes with 2 differ significantly in yield and enantiomeric purity. In the latter reactions, the ee's of the cyclobutane products are consistently much higher than those of the dihydrobenzofuran products. More significantly, products of different absolute configuration result from different cycloalkenes. With 1-anisylcyclopentene or 1-anisylcyclohexene, all of the products are of similar configuration and are obtained in comparable yields and ee's. However, 1-anisylcycloheptene affords products that are diastereomeric with those of the 1-anisylcyclopentene, and in lower ee's. A mechanistic model is proposed. Application of these reactions to the enantioselective synthesis of the pterocarpan class of isoflavonoid natural products is also reported.
• ENGLER, THOMAS A.;REDDY, JAYACHANDRA P.;COMBRINK, KEITH D.;VANDER, VELDE +, J. ORG. CHEM., 55,(1990) N, C. 1248-1254
  作者：ENGLER, THOMAS A.、REDDY, JAYACHANDRA P.、COMBRINK, KEITH D.、VANDER, VELDE +

  DOI：——

  日期：——
• Flavonoid analogues from Pterocarpus species
  作者：Barend C.B. Bezuidenhoudt、E.Vincent Brandt、Daneel Ferreira

  DOI：10.1016/s0031-9422(00)81448-x

  日期：1987.1.28

  erocarpan and a new santal analogue were isolated from the heartwood of P. soyauxii. These are accompanied by several known pterocarpans, isoflavans, isoflavones and trans-pterostilbene. From the heartwood of P. marsupium were obtained 8-C-β- d -glucopyranosyl-3,7,4′-trihydroxy- and -3,7,3′,4′-tetrahydroxyflavone, representative of the first 5-deoxy C-C-coupled flavonol glucosides, and the rare 3′-C-β-

  摘要 从P. soyauxii 的心材中分离到了两种新型翼果木，8-羟基-3,9-二甲氧基-和3,8-二羟基-9-甲氧基翼果木以及一种新的檀香类似物。这些伴随着几种已知的紫檀、异黄烷、异黄酮和反式紫檀芪。从 P. marsupium 的心材中获得了 8-C-β-d-吡喃葡萄糖基-3,7,4'-三羟基-和 -3,7,3',4'-四羟基黄酮，代表第一个 5-脱氧 CC -偶联的黄酮醇糖苷，和罕见的 3'-C-β-d-吡喃葡萄糖基-α-羟基二氢查尔酮，它们的结构是通过高分辨率 NMR 技术确定的。