(-)-(7'E,7R,8S)-3,4,5'-trimethoxy-4',7-epoxy-8,3'-neolign-7'-ene-9,9'-diol | 215228-51-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (-)-(7'E,7R,8S)-3,4,5'-trimethoxy-4',7-epoxy-8,3'-neolign-7'-ene-9,9'-diol
• 英文别名: (E)-3-[(2R,3S)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-ol
• CAS: 215228-51-6
• 化学式: C₂₁H₂₄O₆
• 分子量: 372.418
• InChiKey: IATWXYMZKVGQLC-CGJGEUGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-(7'E,7R,8S)-3,4,5'-trimethoxy-4',7-epoxy-8,3'-neolign-7'-ene-9,9'-diol 在 PtO₂/C 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以74%的产率得到3',4-O-dimethylcedrusin
  参考文献：
  名称：

  On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

  摘要：

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00725-x
• 作为产物：
  描述：

  (E)-3-[(2R,3S)-2,3-dihydro-3-hydroxymethyl-7-methoxy-2-(3'-methoxy-4'-methoxymethoxyphenyl)-1-benzo[b]furan-5-yl]-2-propenal 在 盐酸 、 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 5.0h， 生成 (-)-(7'E,7R,8S)-3,4,5'-trimethoxy-4',7-epoxy-8,3'-neolign-7'-ene-9,9'-diol
  参考文献：
  名称：

  On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton

  摘要：

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00725-x

文献信息

• (7R,8S) and (7S,8R) 8-5' Linked Neolignans from Egyptian Herbal Medicine Anastatica hierochuntica and Inhibitory Activities of Lignans on Nitric Oxide Production
  作者：Masayuki Yoshikawa、Toshio Morikawa、Fengming Xu、Shin Ando、Hisashi Matsuda

  DOI：10.3987/com-03-9804

  日期：——

  Three new (7R,8S) and (7S,8R) 8-5' linked neolignans named hierochins A (1), B (2), and C (3) were isolated from an Egyptian herbal medicine, the whole plants of Anastatica hierochuntica. The absolute stereostructures of new compounds were elucidated on the basis of chemical and physicochemical evidence. Both enantiomers, (7R,8S) and (7S,8R)-type neolignans, were found to coexist in a state of a little differing functional structure. The effects of isolated lignans on nitric oxide production in lipopolysaccharide-activated macrophages were examined and three known neolignan constituents were found to show inhibitory effects on nitric oxide production and induction of inducible nitric oxide synthase.
• On the absolute structure of optically active neolignans containing a dihydrobenzo[b]furan skeleton
  作者：Mabel S.M. Yuen、Feng Xue、Thomas C.W. Mak、Henry N.C. Wong

  DOI：10.1016/s0040-4020(98)00725-x

  日期：1998.10

  Several optically pure neolignans containing a dihydrobenzo[b]furan skeleton were synthesized. Based on an X-ray crystallographic study and circular dichroism results, the absolute configurations of some naturally occurring neolignans, namely balanophonin (1), PGI(2) inducer (2), dehydrodiconiferyl alcohol-4-beta-D-glucoside (3), dehydroconiferyl alcohol (4) and 3',4-di-O-methyicedrusin (5) have been unambiguously established. (C) 1998 Elsevier Science Ltd. All rights reserved.