β-cyclodextrin-2,3-mannoepoxide | 84648-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-cyclodextrin-2,3-mannoepoxide
• 英文别名: 2,3-mannoepoxy-β-cyclodextrin；β-Cyclodextrin epoxide；(2AS)-2A,3A-Anhydro-|A-cyclodextrin；(1R,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,34S,36S,37R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R,50R)-5,10,15,20,25,30,37-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,35,38-pentadecaoxanonacyclo[31.3.2.23,6.28,11.213,16.218,21.223,26.228,31.034,36]pentacontane-39,40,41,42,43,44,45,46,47,48,49,50-dodecol
• CAS: 84648-78-2
• 化学式: C₄₂H₆₈O₃₄
• 分子量: 1116.98
• InChiKey: LTVJQXPMFBBVKC-GPJUQIEOSA-N

物化性质

• 熔点：
  260-263 °C
• 密度：
  1.608±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14
• 重原子数：
  76
• 可旋转键数：
  7
• 环数：
  21.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  526
• 氢给体数：
  19
• 氢受体数：
  34

反应信息

• 作为反应物：
  描述：

  β-cyclodextrin-2,3-mannoepoxide 在 羟胺 作用下， 反应 24.0h， 生成 3-deoxy-3-(N-hydroxylamino)-β-cyclodextrin
  参考文献：
  名称：

  Preassociating .alpha.-Nucleophiles Based on .beta.-Cyclodextrin. Their Synthesis and Reactivity

  摘要：

  Methods are reported for the attachment of alpha-nucleophiles to the primary and secondary sides of the cyclodextrin cavity. Six new materials have been prepared in which beta CD has been modified by hydrazine, hydroxylamine, oxime, and hydroperoxide functionalities. Transacylating studies with p-NPA have demonstrated that the primary-side hydroxylamine shows the highest reactivity with a 1900-fold increase in rate over beta CD at pH 6.5. Other alpha-nucleophiles show less remarkable rate increases in this system but, in some cases, demonstrate hydrogen-bonding to the cyclodextrin rim and inhibition kinetics.

  DOI：

  10.1021/ja00147a005
• 作为产物：
  描述：

  在 potassium carbonate 作用下， 生成 β-cyclodextrin-2,3-mannoepoxide
  参考文献：
  名称：

  The first successful investigation into a cyclodextrin-based enzyme model as an efficient catalyst for luminol chemiluminescent reaction

  摘要：

  首次发现环糊精二聚体的 Ce（IV）络合物能显著增强发光酚-H2O2 系统的化学发光。

  DOI：

  10.1039/b111018g

文献信息

• General method for preparing altrosides from 2,3-manno-epoxides and its application to synthesis of alternative β-cyclodextrin with an altroside as the constituent of macrocyclic structure
  作者：Kahee Fujita、Kazuko Ohta、Yoshihiro Ikegami、Hideaki Shimada、Tsutomu Tahara、Yasuyoshi Nogami、Toshitaka Koga、Kazuki Saito、Terumi Nakajima

  DOI：10.1016/0040-4039(94)88515-x

  日期：1994.12

  A general and convenient method for preparing altrosides from 2,3-manno-epoxides is described and as the application, 2A(S),3A(R)-β-Cyclodextrin which has an altroside as the constituent was prepared and assigned;the altroside part has 1C4 conformation predominantly.

  描述了一种由2，3-甘露聚糖环氧化物制备皂苷的通用且方便的方法，并且作为申请，制备并指定了以皂苷为成分的2 A（S），3 A（R）-β-环糊精。皂苷部分主要具有1 C 4构象。
• Cyclodextrin-accelerated cleavage of phenyl esters: is it the 2-hydroxy or the 3-hydroxy that promotes the acyl transfer?
  作者：Makoto Fukudome、Yuji Okabe、De-Qi Yuan、Kahee Fujita

  DOI：10.1039/a902123j

  日期：——

  Both 2- and 3-monothiocyclodextrins have been synthesized and used in probing the mechanism of cyclodextrin-mediated cleavage of phenyl esters, showing that the 3-thiols are much more effective than the 2-thiols in promoting the acyl transfer.

  已经合成了2-和3-单硫环糊精，并用于探讨环糊精介导的苯基酯裂解机制，结果表明，3-硫醇在促进酰基转移方面远比2-硫醇更有效。
• Preparation and self-inclusion properties of p-xylylenediamine-modified β-cyclodextrins: dependence on the side of modification
  作者：Kwanghee Koh Park、Young Sin Kim、Soo Yeon Lee、Hee Eun Song、Joon Woo Park

  DOI：10.1039/b105388b

  日期：2001.11.1

  β-Cyclodextrin (β-CDx) derivatives modified with p-xylylenediamine at the 3-position, mono-3-deoxy-3-[4-(aminomethyl)benzylamino]-β-CDx (1; β-CDx-3-p-xylylenediamine) was prepared by the reaction of β-CDx-2,3-manno-epoxide with p-xylylenediamine. The circular dichroism properties of 1 are compared with those of the corresponding β-CDx derivative modified at the primary side (2; β-CDx-6-p-xylylenediamine), in the presence and in the absence of 1-adamantanamine·HCl. The results indicate that the xylylenediamine group of 2 is self-included in the β-CDx cavity, whereas that of 1 stays outside the cavity. The energy obtained by molecular modeling showed the same trend. The dependence of self-inclusion behavior of a pendant group in modified cyclodextrins on the position of modification could be a useful guide for designing cyclodextrin derivatives for various applications.

  δ-环糊精（δ-CDx）衍生物在 3 位被对羟基二胺修饰，单-3-脱氧-3-[4-（氨基甲基）苄基氨基]-δ-CDx（1；δ-CDx-3-对羟基二胺）是由δ-CDx-2,3-甲酰环氧化物与对羟基二胺反应制备的。在 1-金刚烷胺-HCl存在和不存在的情况下，将 1 的圆二色性与相应的δ-CDx 衍生物（2；δ-CDx-6-p-xylylenediamine）的主侧修饰的圆二色性进行了比较。结果表明，2 的二氨基己二胺基团自包含在 δ-CDx 的空腔中，而 1 的二氨基己二胺基团则停留在空腔之外。通过分子建模获得的能量也显示出同样的趋势。改性环糊精中悬垂基团的自包容行为与改性位置的关系可为设计各种用途的环糊精衍生物提供有用的指导。
• Supramolecular dioxygen receptors composed of an anionic water-soluble porphinatoiron(<scp>ii</scp>) and cyclodextrin dimers
  作者：Koji Kano、Syoichi Chimoto、Mariko Tamaki、Yoshiki Itoh、Hiroaki Kitagishi

  DOI：10.1039/c1dt11596k

  日期：——

  it is concluded that the imidazole axial ligand at the linker attached at the 3- and 3′-positions of the cyclodextrin units causes higher O2 affinity as compared with the imidazole ligand at the 2- and 2′-positions and the pyridine ligand at the 2,2′- or 3,3′-positions. The electron donating ability and orientation of the axial ligand may control the O2 affinity of a supramolecular receptor.

  三种类型的per- Ø甲基化的β环糊精二聚体，Im2CD，Im3NHCD和Py3NHCD，制备成珠模型。Im2CD是通过单（2 A-氨基）-过-O-甲基化的β-环糊精与3-（1 H-咪唑-1-基）戊二酸的缩合反应合成的。Im3NHCD和Py3NHCD是通过单（2 A，3 A-环氧）-过-O-甲基化的β-环糊精与3-（1 H-咪唑-1-基）戊烷-1,5-的S N 2反应获得的二胺和3,5-双（氨基甲基）吡啶。这些环糊精二聚体形成四（4-磺酰基苯基）卟啉铁的II超分子包合物（II）（Fe II TPPS）在水溶液中。超分子复合物结合了双氧（O 2），Fe II TPPS / Im3NHCD复合物（P 1/2 O2 = 1.5±0.1 Torr）的O 2亲和力远高于Fe II TPPS / Im2CD（36± 2 Torr）和Fe II TPPS / Py3NHCD配合物（70±5 Torr）。
• Dansyl-<i>β</i>-cyclodextrins as Fluorescent Sensors Responsive to Organic Compounds
  作者：Yong Wang、Tsukasa Ikeda、Hiroshi Ikeda、Akihiko Ueno、Fujio Toda

  DOI：10.1246/bcsj.67.1598

  日期：1994.6

  6-O-, 2-O-, and 3-O-Dansyl-β-cyclodextrins (1, 2, and 3) were synthesized and characterized. Compounds 1 and 2 decrease their fluorescence intensities upon intermolecular complex formation. This property enables 1 and 2 to act as fluorescent sensors, converting binding of organic compounds into fluorescence variations.

  合成并鉴定了 6-O-、2-O-和 3-O-丹酰-β-环糊精（1、2 和 3）。化合物 1 和 2 在分子间形成复合物时会降低其荧光强度。这一特性使 1 和 2 能够充当荧光传感器，将有机化合物的结合转化为荧光变化。