(1S,3R,4R,6R,8R,9R,11R,13S,14S,15R,16S,18R,19R,21R,23R,24R,26R,28S,29S,30R,32S,37S,39R,40S,41R,42S,43R,44S,45R,46S)-14,15,29,30,39,40,41,42,43,44,45,46-dodecamethoxy-4,9,19,24-tetrakis(methoxymethyl)-2,5,7,10,12,17,20,22,25,27,31,38-dodecaoxa-34,35-dithiaoctacyclo[14.14.8.23,6.28,11.218,21.223,26.013,37.028,32]hexatetracontane | 1256487-32-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,4R,6R,8R,9R,11R,13S,14S,15R,16S,18R,19R,21R,23R,24R,26R,28S,29S,30R,32S,37S,39R,40S,41R,42S,43R,44S,45R,46S)-14,15,29,30,39,40,41,42,43,44,45,46-dodecamethoxy-4,9,19,24-tetrakis(methoxymethyl)-2,5,7,10,12,17,20,22,25,27,31,38-dodecaoxa-34,35-dithiaoctacyclo[14.14.8.23,6.28,11.218,21.223,26.013,37.028,32]hexatetracontane
• CAS: 1256487-32-7
• 化学式: C₅₂H₉₀O₂₈S₂
• 分子量: 1227.4
• InChiKey: FKGSFNJXZOXANQ-OQWQTNIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  82
• 可旋转键数：
  20
• 环数：
  13.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  309
• 氢给体数：
  0
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6R,8R,9R,11R,13S,14S,15R,16S,18R,19R,21R,23R,24R,26R,28S,29S,30R,32S,37S,39R,40S,41R,42S,43R,44S,45R,46S)-14,15,29,30,39,40,41,42,43,44,45,46-dodecamethoxy-4,9,19,24-tetrakis(methoxymethyl)-2,5,7,10,12,17,20,22,25,27,31,38-dodecaoxa-34,35-dithiaoctacyclo[14.14.8.23,6.28,11.218,21.223,26.013,37.028,32]hexatetracontane 在 Cleland's reagent 作用下， 反应 4.0h， 生成
  参考文献：
  名称：

  α-Cyclodextrins reversibly capped with disulfide bonds

  摘要：

  Per-O-methyl-6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin 在 pH 9 下经历空气氧化，专门形成具有分子内二硫键覆盖 C6I 和 C6IV 位置的单体。相反，其非甲基化类似物6I,6IV-二硫基-6I,6IV-二脱氧-α-环糊精在相同条件下给出单体和二聚体的混合物。分子模型表明，在两种单体情况下，二硫键有效地封闭了环糊精空腔的初级边缘。封端环糊精的二硫键可以通过用二硫苏糖醇还原来裂解。因此，大循环系统可以通过施加外部刺激来互换开放式和杯状形式。

  DOI：

  10.1039/c0nj00126k
• 作为产物：
  描述：

  在 air 作用下， 反应 48.0h， 生成 (1S,3R,4R,6R,8R,9R,11R,13S,14S,15R,16S,18R,19R,21R,23R,24R,26R,28S,29S,30R,32S,37S,39R,40S,41R,42S,43R,44S,45R,46S)-14,15,29,30,39,40,41,42,43,44,45,46-dodecamethoxy-4,9,19,24-tetrakis(methoxymethyl)-2,5,7,10,12,17,20,22,25,27,31,38-dodecaoxa-34,35-dithiaoctacyclo[14.14.8.23,6.28,11.218,21.223,26.013,37.028,32]hexatetracontane
  参考文献：
  名称：

  α-Cyclodextrins reversibly capped with disulfide bonds

  摘要：

  Per-O-methyl-6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin 在 pH 9 下经历空气氧化，专门形成具有分子内二硫键覆盖 C6I 和 C6IV 位置的单体。相反，其非甲基化类似物6I,6IV-二硫基-6I,6IV-二脱氧-α-环糊精在相同条件下给出单体和二聚体的混合物。分子模型表明，在两种单体情况下，二硫键有效地封闭了环糊精空腔的初级边缘。封端环糊精的二硫键可以通过用二硫苏糖醇还原来裂解。因此，大循环系统可以通过施加外部刺激来互换开放式和杯状形式。

  DOI：

  10.1039/c0nj00126k

文献信息

• α-Cyclodextrins reversibly capped with disulfide bonds
  作者：Lukáš Kumprecht、Miloš Buděšínský、Petr Bouř、Tomáš Kraus

  DOI：10.1039/c0nj00126k

  日期：——

  Per-O-methyl-6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin undergoes air oxidation at pH 9 to exclusively form a monomeric species having an intramolecular disulfide linkage capping the C6I and C6IV positions. In contrast, its non-methylated analogue, 6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin, gives a mixture of monomeric and dimeric species under the same conditions. Molecular models show that in both cases of the monomeric species, the disulfide bonds effectively close the primary rims of the cyclodextrin cavities. The disulfide bonds of the capped cyclodextrins could be cleaved by reduction with dithiothreitol. Thus, the macrocyclic system can interchange the open-ended and cup-like forms by the application of external stimuli.

  Per-O-methyl-6I,6IV-disulfanyl-6I,6IV-dideoxy-α-cyclodextrin 在 pH 9 下经历空气氧化，专门形成具有分子内二硫键覆盖 C6I 和 C6IV 位置的单体。相反，其非甲基化类似物6I,6IV-二硫基-6I,6IV-二脱氧-α-环糊精在相同条件下给出单体和二聚体的混合物。分子模型表明，在两种单体情况下，二硫键有效地封闭了环糊精空腔的初级边缘。封端环糊精的二硫键可以通过用二硫苏糖醇还原来裂解。因此，大循环系统可以通过施加外部刺激来互换开放式和杯状形式。