(R)-((2R,3S,3aS,6aR)-3-(cinnamoyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate | 1262487-80-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (R)-((2R,3S,3aS,6aR)-3-(cinnamoyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate
• 英文别名: 3,6-anhydro-5,7-bis-(O-cinnamoyl)-2-deoxy-7-C-phenyl-D-glycero-D-gluco-heptono-1,4-lactone；(+)-dicinnamoyl goniofufurone；[(2R,3S,3aS,6aR)-5-oxo-2-[(R)-phenyl-[(E)-3-phenylprop-2-enoyl]oxymethyl]-3,3a,6,6a-tetrahydro-2H-furo[3,2-b]furan-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 1262487-80-8
• 化学式: C₃₁H₂₆O₇
• 分子量: 510.543
• InChiKey: DQJWUTFOIIPQBE-PCLLYBOASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (R)-((2R,3R,4R)-3-(cinnamoyloxy)-4,5-dihydroxy-tetrahydrofuran-2-yl)(phenyl)methyl cinnamate 在 丙二酸环(亚)异丙酯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以83%的产率得到(R)-((2R,3S,3aS,6aR)-3-(cinnamoyloxy)-5-oxo-hexahydrofuro[3,2-b]furan-2-yl)(phenyl)methyl cinnamate
  参考文献：
  名称：

  Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone

  摘要：

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2010.10.016

文献信息

• Design, synthesis and SAR analysis of antitumour styryl lactones related to (+)-crassalactones B and C
  作者：Goran Benedeković、Mirjana Popsavin、Jovana Francuz、Ivana Kovačević、Vesna Kojić、Gordana Bogdanović、Vladimir Divjaković、Velimir Popsavin

  DOI：10.1016/j.ejmech.2014.09.064

  日期：2014.11

  A series of styryl lactones containing the cinnamic acid ester groups such as (+)-crassalactones B (3a) and C (4a), 5,7-di-O-cinamoyl derivative 6, the corresponding 7-epimers and 7-deoxy derivatives have been synthesized, characterized and evaluated for their in vitro antitumour activity against a panel of several human tumour cell lines. Twelve new analogues such as 5-O- or 7-O-(4-methoxycinnamoyl)

  一系列含有肉桂酸酯基的苯乙烯基内酯，如（+）-crasSAlactones B（3a）和C（4a），5,7- di - O - cinamoyl衍生物6，相应的7-epimers和7-deoxy衍生物已经合成，表征和评估了它们对一组人肿瘤细胞系的体外抗肿瘤活性。十二个新的类似物，例如5- O-或7 - O-（4-甲氧基肉桂酰基），5- O-或7 - O-（4-硝基肉桂酰基）和5- O-或7 - O-（4-氟肉桂酰基）酯goniofufurone（ - （+）的图3b - d），7-外延在SAR研究中，已经准备好使用-（+）-goniofufurone（epi - 3b - d）以及7-脱氧衍生物5b - d来关联所有化合物。一些类似物对选定的人类肿瘤细胞系显示出强大的抗增殖作用，但没有一个对正常胎儿肺成纤维细胞（MRC-5）具有细胞毒性。因此，发现7- epi- crasSAlactone