cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-3-oxatricyclo[3.2.0.0^2,6]decane | 370888-70-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-3-oxatricyclo[3.2.0.0^2,6]decane
• 英文别名: (1R,2R,6R,8R,9R,12R)-4,4-dimethyl-1-phenylmethoxy-3,5,7-trioxatetracyclo[6.5.0.02,6.09,12]tridecane
• CAS: 370888-70-3
• 化学式: C₁₉H₂₄O₄
• 分子量: 316.397
• InChiKey: HNXIMMXOYVDINR-FEFVAOQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-3-oxatricyclo[3.2.0.0^2,6]decane 在 palladium on activated charcoal 高氯酸 、 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 cis-syn-cis-4α,5α-O-isopropylidene-6α-hydroxy-3-oxatricyclo[3.2.0.0^2,6]decane
  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
• 作为产物：
  描述：

  (3aR,5R,6R,6aR)-6-Allyl-6-benzyloxy-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxole 在 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 作用下， 以 乙醚 为溶剂， 反应 3.5h， 以73%的产率得到cis-syn-cis-4α,5α-O-isopropylidene-6α-benzyloxy-3-oxatricyclo[3.2.0.0^2,6]decane
  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

文献信息

• Intramolecular [2 + 2] Photocycloaddition of Alkenes Incorporated in a Carbohydrate Template. Synthesis of Enantiopure Bicyclo[3.2.0]heptanes and -[6.3.0]undecanes
  作者：Shyamapada Banerjee、Subrata Ghosh

  DOI：10.1021/jo026920c

  日期：2003.5.1

  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.