(4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate | 1262487-73-9

• 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: (4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate
• 英文别名: ethyl (E,4S,5R,6R,7R)-4,6-dihydroxy-7-phenyl-7-[(E)-3-phenylprop-2-enoyl]oxy-5-prop-2-enoxyhept-2-enoate
• CAS: 1262487-73-9
• 化学式: C₂₇H₃₀O₇
• 分子量: 466.531
• InChiKey: LBFUXTLSCPNKCK-VNIYMLBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以70%的产率得到(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl 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
• 作为产物：
  描述：

  (R)-((2R,3R,4R)-3-(allyloxy)-4,5-dihydroxy-tetrahydrofuran-2-yl)(phenyl)methyl cinnamate 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 反应 2.0h， 以72%的产率得到(4S,5R,6R,7R,E)-ethyl 5-(allyloxy)-7-cinnamoyloxy-4,6-dihydroxy-7-phenylhept-2-enoate
  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

• Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone
  作者：Gangavaram V.M. Sharma、Samala Mallesham

  DOI：10.1016/j.tetasy.2010.10.016

  日期：2010.11

  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