Mono-2-O-allyl-α-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Mono-2-O-allyl-α-cyclodextrin
• 英文别名: 2-O-allyl-α-CD；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31R,32R,33R,34R,35R,36R,37R,38R,39R,40R,41S,42R)-5,10,15,20,25,30-hexakis(hydroxymethyl)-42-prop-2-enoxy-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontane-31,32,33,34,35,36,37,38,39,40,41-undecol
• 化学式: C₃₉H₆₄O₃₀
• 分子量: 1012.92
• InChiKey: AJNXSGRAKSRYDR-AYBHLYQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -11.7
• 重原子数：
  69
• 可旋转键数：
  9
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  464
• 氢给体数：
  17
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  Mono-2-O-allyl-α-cyclodextrin 在 二甲基硫 、 臭氧 作用下， 生成 2-[[(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,32R,33R,34R,35R,36R,37R,38R,39R,40R,41R,42R)-31,33,34,35,36,37,38,39,40,41,42-undecahydroxy-5,10,15,20,25,30-hexakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.23,6.28,11.213,16.218,21.223,26]dotetracontan-32-yl]oxy]acetaldehyde
  参考文献：
  名称：

  The Synthesis of Functionalized Cyclodextrins As Scaffolds and Templates for Molecular Diversity, Catalysis, and Inclusion Phenomena

  摘要：

  alpha-, beta- and gamma-cyclodextrins were chemically modified to selectively introduce functionality on the primary and secondary faces. Azido and substituted alkenyl groups were selectively introduced on the primary hydroxy groups to give monosubstituted derivatives. The secondary C-2 hydroxy group was selectively functionalized with allyl, 1-hexenyl, carboxymethyl, and omega-azidoalkyl groups (n: 3, 4, 5) as ethers. The chemically modified cyclodextrins are versatile molecules for use as scaffolds and templates in conjunction with chemical diversity, catalysis, and inclusion phenomena.

  DOI：

  10.1021/jo00120a023
• 作为产物：
  描述：

  3-溴丙烯 、 α-环糊精 在 lithium hydride 、 lithium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 26.0h， 生成 Mono-2-O-allyl-α-cyclodextrin
  参考文献：
  名称：

  全套单取代的环麦芽六糖（α-环糊精）作为进一步合成的前体

  摘要：

  将环麦芽六糖（α-环糊精，α-CD）与烯丙基或肉桂基溴化物进行烷基化，然后对剩余的羟基进行过乙酰化并分离异构体，得到一组过乙酰化的2（I）-O-，3（I）-O -和6（I）-O-烷基化的α-CD的产率高达27％。过乙酰化的烯丙基或肉桂基衍生物的臭氧分解或氧化裂解可形成一整套完整的过乙酰化的2（I）-O-，3（I）-O-和6（I）-O-甲酰基甲基或羧甲基衍生物，它们是制备有用的前体α-CD的区域选择性单取代的衍生物。此外，已经提出了一种快速的方法，仅使用它们的（1）H NMR光谱识别彼此的单个2（I）-O-，3（I）-O-和6（I）-O-单取代的过乙酰化CD。

  DOI：

  10.1016/j.carres.2011.08.011

文献信息

• The Synthesis of Functionalized Cyclodextrins As Scaffolds and Templates for Molecular Diversity, Catalysis, and Inclusion Phenomena
  作者：Stephen Hanessian、Aziza Benalil、Craig Laferriere

  DOI：10.1021/jo00120a023

  日期：1995.7

  alpha-, beta- and gamma-cyclodextrins were chemically modified to selectively introduce functionality on the primary and secondary faces. Azido and substituted alkenyl groups were selectively introduced on the primary hydroxy groups to give monosubstituted derivatives. The secondary C-2 hydroxy group was selectively functionalized with allyl, 1-hexenyl, carboxymethyl, and omega-azidoalkyl groups (n: 3, 4, 5) as ethers. The chemically modified cyclodextrins are versatile molecules for use as scaffolds and templates in conjunction with chemical diversity, catalysis, and inclusion phenomena.
• Complete sets of monosubstituted cyclomaltohexaoses (α-cyclodextrins) as precursors for further synthesis
  作者：Michal Řezanka、Jindřich Jindřich

  DOI：10.1016/j.carres.2011.08.011

  日期：2011.11

  remaining hydroxyl groups and separation of isomers, resulted in the set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-alkylated α-CDs in up to 27% yields. Ozonolysis or oxidative cleavage of peracetylated allyl or cinnamyl derivatives resulted in a complete set of peracetylated 2(I)-O-, 3(I)-O- and 6(I)-O-formylmethyl or carboxymethyl derivatives that are useful precursors for preparation of regioselectively

  将环麦芽六糖（α-环糊精，α-CD）与烯丙基或肉桂基溴化物进行烷基化，然后对剩余的羟基进行过乙酰化并分离异构体，得到一组过乙酰化的2（I）-O-，3（I）-O -和6（I）-O-烷基化的α-CD的产率高达27％。过乙酰化的烯丙基或肉桂基衍生物的臭氧分解或氧化裂解可形成一整套完整的过乙酰化的2（I）-O-，3（I）-O-和6（I）-O-甲酰基甲基或羧甲基衍生物，它们是制备有用的前体α-CD的区域选择性单取代的衍生物。此外，已经提出了一种快速的方法，仅使用它们的（1）H NMR光谱识别彼此的单个2（I）-O-，3（I）-O-和6（I）-O-单取代的过乙酰化CD。