6^A-(4-methylamino-3-nitrobenzyl)-β-cyclodextrin

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A-(4-methylamino-3-nitrobenzyl)-β-cyclodextrin
• 英文别名: 6-O-(4-methylamino-3-nitrobenzyl)-β-cyclodextrin；(1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-5,10,15,20,30,35-hexakis(hydroxymethyl)-25-[[4-(methylamino)-3-nitrophenyl]methoxymethyl]-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecol
• 化学式: C₅₀H₇₈N₂O₃₇
• 分子量: 1299.16
• InChiKey: DRDYRVUOVIDXGG-SPNHVSLSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.6
• 重原子数：
  89
• 可旋转键数：
  11
• 环数：
  22.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  601
• 氢给体数：
  21
• 氢受体数：
  38

反应信息

• 作为产物：
  描述：

  4-(chloromethyl)-N-methyl-2-nitrobenzenamine 、 β-环糊精 生成 6^A-(4-methylamino-3-nitrobenzyl)-β-cyclodextrin
  参考文献：
  名称：

  β-环糊精次级侧的选择性保护

  摘要：

  据报道，在干燥的DMF中，在NaH存在下，通过与叔丁基二甲基甲硅烷基氯反应，对β-环糊精的次级侧进行了选择性保护。尽管所有羟基均未在该反应中被甲硅烷基化，但这些基团可提供空间保护，并将进入的亲电子体引导至分子的初级侧。

  DOI：

  10.1016/s0040-4039(00)78537-6

文献信息

• Selective protection of the secondary side of β-cyclodextrin
  作者：Shengping Tian、Valerian T. D'Souza

  DOI：10.1016/s0040-4039(00)78537-6

  日期：1994.12

  Selective protection of the secondary side of β-cyclodextrin by reaction with t-butyldimethylsilyl chloride in the presence of NaH in dry DMF, is reported. Although, all the hydroxyl groups are not silylated in this reaction, these groups offer steric protection and direct the incoming electrophile to the primary side of the molecule.

  据报道，在干燥的DMF中，在NaH存在下，通过与叔丁基二甲基甲硅烷基氯反应，对β-环糊精的次级侧进行了选择性保护。尽管所有羟基均未在该反应中被甲硅烷基化，但这些基团可提供空间保护，并将进入的亲电子体引导至分子的初级侧。
• Selectively Monomodified Cyclodextrins. Synthetic Strategies
  作者：Shengping Tian、Henghu Zhu、Peter Forgo、Valerian T. D'Souza

  DOI：10.1021/jo991347r

  日期：2000.5.1

  ;Monomodifications of cyclodextrins to give selectively 2-, 3-, or 6-substituted product is a challenging task because of the number of hydroxyl groups that can potentially react with the incoming reagent. The principles and the methods involved in manipulations of the differences in the chemistry of these hydroxyl groups to control the outcome of an electrophilic reaction with them to produce monoalkylated (ether-linkaged) cyclodextrin derivatives are discussed and illustrated.