(1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate | 1262487-74-0

• 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: (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate
• 英文别名: [(1R,2R)-2-hydroxy-2-[(2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl]-1-phenylethyl] (E)-3-phenylprop-2-enoate
• CAS: 1262487-74-0
• 化学式: C₂₂H₂₂O₅
• 分子量: 366.414
• InChiKey: ZKWPLIJKMRIATQ-FYGRDRRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate 、 肉桂酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以73%的产率得到(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)
  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：

  (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

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