(+)-Mirandin A | 62163-23-9

• 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: (+)-Mirandin A
• 英文别名: Mirandin A；(2S,3R,3aS)-3a-methoxy-3-methyl-5-prop-2-enyl-2-(3,4,5-trimethoxyphenyl)-2,3-dihydro-1-benzofuran-6-one
• CAS: 62163-23-9
• 化学式: C₂₂H₂₆O₆
• 分子量: 386.445
• InChiKey: MRRHZTMSIVTFSK-XOJPMGEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (+)-Mirandin A 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 15.0h， 以76%的产率得到(1R,5R,6R,7R)-3-Allyl-5-methoxy-6-methyl-7-(3,4,5-trimethoxy-phenyl)-bicyclo[3.2.1]oct-3-ene-2,8-dione
  参考文献：
  名称：

  来自 Nectandra 物种的新木脂素

  摘要：

  摘要 Amazonian Nectandra (Lauraceae) 物种的树干木材含有一种双环[3.2.1] 辛烷和四种氢苯并呋喃新木脂素。后者包括 mirandin、重排 burchellin 和 burchellin 类型的代表。前者的特征为 (1 S , 4 R , 5 S , 6 R , 7 R )-3-烯丙基-4-羟基-1-甲氧基-(3', 4', 5'-三甲氧基苯基)-7-甲基-8-oxobicyclo[3.2.1]oct-2-ene macrophyllin-B)，一种看似罕见的macrophyllin类型的新代表。

  DOI：

  10.1016/0031-9422(80)87033-6
• 作为产物：
  描述：

  反式-3,4,5-三甲氧基肉桂醇 在 lead(IV) acetate 、 三苯基膦 、 N,N-二乙基苯胺 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.5h， 生成 (+)-Mirandin A
  参考文献：
  名称：

  Structure-activity relationships of kadsurenone analogues

  摘要：

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

  DOI：

  10.1021/jm00384a023

文献信息

• Structure-activity relationships of kadsurenone analogues
  作者：Mitree M. Ponpipom、Robert L. Bugianesi、David R. Brooker、Bao-zhen Yue、San-bao Hwang、Tsung-ying Shen

  DOI：10.1021/jm00384a023

  日期：1987.1

  Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.
• Neolignans from a Nectandra species
  作者：Raimundo Braz Filho、Roberto Figliuolo、Otto R. Gottlieb

  DOI：10.1016/0031-9422(80)87033-6

  日期：1980.1

  Abstract The trunk wood of an Amazonian Nectandra (Lauraceae) species contains one bicyclo[3.2.1]octanoid and four hydrobenzofuranoid neolignans. The latter comprise representatives of the mirandin, the rearranged burchellin and the burchellin types. The former was characterized as (1 S , 4 R , 5 S , 6 R , 7 R )-3-allyl-4-hydroxy-1-methoxy-(3′, 4′, 5′-trimethoxyphenyl)- 7-methyl-8-oxobicyclo[3.2.1]oct-2-ene

  摘要 Amazonian Nectandra (Lauraceae) 物种的树干木材含有一种双环[3.2.1] 辛烷和四种氢苯并呋喃新木脂素。后者包括 mirandin、重排 burchellin 和 burchellin 类型的代表。前者的特征为 (1 S , 4 R , 5 S , 6 R , 7 R )-3-烯丙基-4-羟基-1-甲氧基-(3', 4', 5'-三甲氧基苯基)-7-甲基-8-oxobicyclo[3.2.1]oct-2-ene macrophyllin-B)，一种看似罕见的macrophyllin类型的新代表。