(+)-tricinnamate | 918872-27-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (+)-tricinnamate
• 英文别名: (2E,2'E)-((1R,2R)-1-((2R,3S)-3-(cinnamoyloxy)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-2-phenylethane-1,2-diyl) bis(3-phenylacrylate)；[(2R,3S)-6-oxo-2-[(1R,2R)-2-phenyl-1,2-bis[[(E)-3-phenylprop-2-enoyl]oxy]ethyl]-2,3-dihydropyran-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 918872-27-2
• 化学式: C₄₀H₃₂O₈
• 分子量: 640.689
• InChiKey: JMIJICDNFOKZPY-YRSBBBKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  48
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (2E,2'E)-((1R,2R)-1-((2R,3S)-3-(cinnamoyloxy)-3,6-dihydro-2H-pyran-2-yl)-2-phenylethane-1,2-diyl) bis(3-phenylacrylate) 在 pyridinium dichromate 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以85%的产率得到(+)-tricinnamate
  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

• Cytotoxic Styryl-Lactones from the Leaves and Twigs of <i>Polyalthia crassa</i>
  作者：Patoomratana Tuchinda、Bamroong Munyoo、Manat Pohmakotr、Pongchan Thinapong、Samaisukh Sophasan、Thawatchai Santisuk、Vichai Reutrakul

  DOI：10.1021/np060323u

  日期：2006.12.1

  (+)-howiinol A. Their structures were determined on the basis of spectroscopic methods. The absolute configuration of 1-3 was established by chemical conversions. Single-crystal X-ray analysis and the Mosher ester method were used to confirm the absolute stereochemistry of 4. Cytotoxic evaluation against several mammalian cancer cell lines was performed on all new isolates, aristolactam AII, and the modified

  从重症紫薇的叶和细枝的可溶于乙酸乙酯的细胞毒性提取物中分离出四种新的苯乙烯基内酯，crassalactones AD（1-4），以及七种已知化合物，（+）-3-乙酰基甲内酯，（+） -甲内酯，马兜铃AII，肉桂酸，（+）-角呋喃酮，（+）-角吡喃酮和（+）-异戊醇A。它们的结构是在光谱法的基础上确定的。1-3的绝对构型是通过化学转化建立的。使用单晶X射线分析和Mosher酯法确认了4的绝对立体化学。对所有新分离株马兜铃内酰胺AII和修饰的（+）-三丁氨酸衍生物11进行了针对几种哺乳动物癌细胞系的细胞毒性评估。从1获得。