(E)-4-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-but-2-enoic acid ethyl ester | 370888-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-4-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-but-2-enoic acid ethyl ester
• 英文别名: ethyl (E)-4-[(3aR,5R,6R,6aR)-5-ethenyl-2,2-dimethyl-6-phenylmethoxy-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]but-2-enoate
• CAS: 370888-76-9
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: AWZNKFXUSAHSMC-MJTQEFRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-4-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-but-2-enoic acid ethyl ester 在 palladium on activated charcoal 高氯酸 、 二苯甲酮 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 5.0h， 生成 cis-syn-cis-4α,5α-O-isopropylidene-6α-hydroxy-9-carbethoxy-3-oxatricyclo[3.2.0.0^2,6]decane
  参考文献：
  名称：

  Intramolecular [2 + 2] Photocycloaddition of Alkenes Incorporated in a Carbohydrate Template. Synthesis of Enantiopure Bicyclo[3.2.0]heptanes and -[6.3.0]undecanes

  摘要：

  Intramolecular [2 + 2] photocycloaddition of alkenes with a furano sugar placed between them have been investigated under both copper(l)-catalyzed and sensitized conditions. The copper(l)catalyzed photocycloaddition of the dienes 4a, 4b, and 4c led to unexpected formation of the thermodynamically less stable cis-syn-cis 4-5-5 tricyclic adducts 5a, 5b, and 5c, respectively. The sensitized photocycloaddition of the diene 14 also gave the cis-syn-cis adduct 15 showing that the copper(I) catalyst does not have any influence on the stereochemical course through coordination with the anomeric ring oxygen of the furano sugar. The identical stereochemical course observed under both catalyzed and sensitized photoaddition reactions have been attributed to be of steric origin. Bis(dienes) 25a and 25b, which gave an intractable mixture on copper(l)-catalyzed irradiation, underwent smooth photocycloaddition in the presence of benzophenone, and the resulting 1,2-divinyl cyclobutanes underwent spontaneous [3.3]-rearrangement at room temperature to produce bicyclo[6.3.0]undecanes 30a and 30b, respectively. This investigation provides an approach for the construction of enantiopure bicyclo[3.2.0]heptanes and -[6.3.0]undecanes.

  DOI：

  10.1021/jo026920c
• 作为产物：
  描述：

  (E)-4-[(3aR,5R,6R,6aR)-6-Benzyloxy-5-(1,2-dihydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-but-2-enoic acid ethyl ester 在 咪唑 、 碘 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 (E)-4-((3aR,5R,6R,6aR)-6-Benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-but-2-enoic acid ethyl ester
  参考文献：
  名称：

  Intramolecular [2+2] photocycloaddition of 1,6-dienes incorporated in a furanose ring. Unusual formation of cis-syn-cis 6-oxatricyclo[6.2.0.03,7]decanes

  摘要：

  Intramolecular [2+2] photocycloaddition of 1,6-dienes incorporated in a furanose ring either in the presence of a copper(I) catalyst or with a sensitiser led to the unusual formation of cis-syn-cis adducts. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01167-4