(R)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl cinnamate | 1262487-75-1

• 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)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl cinnamate
• CAS: 1262487-75-1
• 化学式: C₂₅H₂₆O₅
• 分子量: 406.478
• InChiKey: XXWQEYWKASJAKV-PLCOYHCASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  30.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (R)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-yl)(phenyl)methyl cinnamate 在 pyridinium dichromate 、 sodium acetate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以69%的产率得到(R)-((4R,4aR,8aS)-2,2-dimethyl-6-oxo-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-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
• 作为产物：
  描述：

  (1R,2R)-2-hydroxy-2-((2R,3S)-3-hydroxy-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl cinnamate 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以82%的产率得到(R)-((4R,4aR,8aS)-2,2-dimethyl-4,4a,6,8a-tetrahydropyrano[3,2-d][1,3]dioxin-4-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