6^I-O-propargyl-γ-cyclodextrin | 1416149-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^I-O-propargyl-γ-cyclodextrin
• 英文别名: (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36S,38R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R,51R,52R,53R,54R,55R,56R)-5,10,15,20,30,35,40-heptakis(hydroxymethyl)-25-(prop-2-ynoxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.23,6.28,11.213,16.218,21.223,26.228,31.233,36]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol
• CAS: 1416149-52-4
• 化学式: C₅₁H₈₂O₄₀
• 分子量: 1335.19
• InChiKey: LHSVXXAGUBPECP-UNQXDLBQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -16.5
• 重原子数：
  91
• 可旋转键数：
  10
• 环数：
  30.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  622
• 氢给体数：
  23
• 氢受体数：
  40

反应信息

• 作为反应物：
  描述：

  6^I-O-propargyl-γ-cyclodextrin 、 乙酸酐 在 三乙胺 作用下， 以95%的产率得到per-O-acetyl-6^I-O-propargyl-γ-cyclodextrin
  参考文献：
  名称：

  Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis

  摘要：

  Regioselective alkylation of gamma-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of gamma-cyclodextrin.

  DOI：

  10.1021/jo301656p
• 作为产物：
  描述：

  3-溴丙炔 、 γ-环糊精 在 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 48.0h， 以13%的产率得到6^I-O-propargyl-γ-cyclodextrin
  参考文献：
  名称：

  Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis

  摘要：

  Regioselective alkylation of gamma-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of gamma-cyclodextrin.

  DOI：

  10.1021/jo301656p

文献信息

• Complete Sets of Monosubstituted γ-Cyclodextrins as Precursors for Further Synthesis
  作者：Markéta Bláhová、Eva Bednářová、Michal Řezanka、Jindřich Jindřich

  DOI：10.1021/jo301656p

  日期：2013.1.18

  Regioselective alkylation of gamma-cyclodextrin with allyl or propargyl bromide, using optimized reaction conditions, followed by peracetylation of the remaining hydroxyl groups and separation of isomers resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated cyclodextrins in up to 19% yields. Ozonolysis or oxidative cleavage of peracetylated allyl derivatives resulted in a complete set of peracetylated 2(I)-O, 3(I)-O-, and 6(I)-O-formylmethyl or -carboxymethyl derivatives. All of these derivatives are useful precursors for further preparation of regioselectively monosubstituted derivatives of gamma-cyclodextrin.