(E)-1-[2′,4′-dihydroxy-(3″R)-(3″-hydroxy-3″,7″-dimethyloct-6″-enyl)phenyl]-3-(4-hydroxyphenyl)propenone | 1529791-38-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (E)-1-[2′,4′-dihydroxy-(3″R)-(3″-hydroxy-3″,7″-dimethyloct-6″-enyl)phenyl]-3-(4-hydroxyphenyl)propenone
• 英文别名: (R)-(-)-xanthoangelol J；(E)-1-[2,4-dihydroxy-3-[(3R)-3-hydroxy-3,7-dimethyloct-6-enyl]phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 1529791-38-5
• 化学式: C₂₅H₃₀O₅
• 分子量: 410.51
• InChiKey: BQRLJINJRBLFJV-CUVMYHFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,7-二甲基-2,6-辛二烯-1-醇 在 2,6-二甲基吡啶 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 L-(+)-酒石酸二乙酯 、 四溴化碳 、 四丁基氟化铵 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， -40.0~80.0 ℃ 、540.01 kPa 条件下， 反应 43.75h， 生成 (E)-1-[2′,4′-dihydroxy-(3″R)-(3″-hydroxy-3″,7″-dimethyloct-6″-enyl)phenyl]-3-(4-hydroxyphenyl)propenone
  参考文献：
  名称：

  Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation

  摘要：

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.11.106

文献信息

• Total synthesis and assignment of the absolute stereochemistry of xanthoangelol J: development of a highly efficient method for Claisen–Schmidt condensation
  作者：Dwipen Kakati、Nabin C. Barua

  DOI：10.1016/j.tet.2013.11.106

  日期：2014.1

  The first total synthesis of cancer chemopreventive terpenyl hydroxychalcone xanthoangelol J isolated from Angelica keiskei was accomplished with asymmetric epoxidation, aromatic C-alkylation and Claisen-Schmidt condensation via enol mode as key steps. The crucial Claisen-Schmidt condensation has been accomplished by a novel green method using KHSO4-SiO2 as a recyclable catalyst under microwave activation. The absolute configuration of the molecule was also determined. (C) 2013 Elsevier Ltd. All rights reserved.