per(2,3-di-O-methyl)-α-cyclodextrin | 118663-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: per(2,3-di-O-methyl)-α-cyclodextrin
• 英文别名: 2A,2B,2C,2D,2E,2F,3A,3B,3C,3D,3E,3F-Dodeca-O-methyl-|A-cyclodextrin；[(1R,3R,5R,6R,8R,10R,11R,13R,15R,16R,18R,20R,21R,23R,25R,26R,28R,30R,31S,32R,33S,34R,35S,36R,37S,38R,39S,40R,41S,42R)-10,15,20,25,30-pentakis(hydroxymethyl)-31,32,33,34,35,36,37,38,39,40,41,42-dodecamethoxy-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-5-yl]methanol
• CAS: 118663-68-6
• 化学式: C₄₈H₈₄O₃₀
• 分子量: 1141.18
• InChiKey: OZAPVJXZLWCMMI-LZJZZLLASA-N

物化性质

• 沸点：
  1053.1±65.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -6.4
• 重原子数：
  78
• 可旋转键数：
  18
• 环数：
  22.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  343
• 氢给体数：
  6
• 氢受体数：
  30

反应信息

• 作为反应物：
  描述：

  per(2,3-di-O-methyl)-α-cyclodextrin 在 碘 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 以32%的产率得到hexakis(2,3-di-O-methyl-6-deoxy-6-iodo)-α-cyclodextrin
  参考文献：
  名称：

  Synthesis and characterisation of O-6-alkylthio- and perfluoroalkylpropanethio-α-cyclodextrins and their O-2-, O-3-methylated analogues

  摘要：

  描述了十二种烷硫基-或全氟烷基丙硫基-α-环糊精衍生物及其O-2-、O-3-甲基化类似物的合成。偶联反应首先涉及烷基全氟丙烷异硫脲碘化物或烷基异硫脲溴化物的碱性原位水解，然后与C-6位被碘或甲基磺酰基修饰的α-环糊精反应。这些新化合物的界面性质已通过对其空气-水界面处的单分子层的研究来确定。

  DOI：

  10.1039/b703894a
• 作为产物：
  描述：

  per(2,3-di-O-methyl-6-O-triphenylmethyl)-α-cyclodextrin 在 tetrafluoroboric acid 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 3.0h， 以96%的产率得到per(2,3-di-O-methyl)-α-cyclodextrin
  参考文献：
  名称：

  First Per-6-O-tritylation of Cyclodextrins

  摘要：

  Because of the large dimension of the trityl group and the truncated conical geometry of cyclodextrin (CD) molecules, it is unclear if there is enough space at the narrower end of CDs to permit a per-6-O-tritylation. This work demonstrates that it is indeed possible to simultaneously install a trityl group at the O6-position of every glucopyranosyl unit in a CD. A novel per-6-substitution method has been developed for CD chemistry.

  DOI：

  10.1021/ol300358u

文献信息

• A Complex Comprising a Cyanine Dye Rotaxane and a Porphyrin Nanoring as a Model Light‐Harvesting System
  作者：Jiratheep Pruchyathamkorn、William J. Kendrick、Andrew T. Frawley、Andrea Mattioni、Felipe Caycedo‐Soler、Susana F. Huelga、Martin B. Plenio、Harry L. Anderson

  DOI：10.1002/anie.202006644

  日期：2020.9.14

  A nanoring‐rotaxane supramolecular assembly with a Cy7 cyanine dye (hexamethylindotricarbocyanine) threaded along the axis of the nanoring was synthesized as a model for the energy transfer between the light‐harvesting complex LH1 and the reaction center in purple bacteria photosynthesis. The complex displays efficient energy transfer from the central cyanine dye to the surrounding zinc porphyrin nanoring

  合成了具有沿纳米环轴延伸的 Cy7 花青染料（六甲基吲哚三碳花青）的纳米环-轮烷超分子组装体，作为光捕获复合物 LH1 与紫色细菌光合作用反应中心之间能量转移的模型。该复合物表现出从中心花青染料到周围锌卟啉纳米环的有效能量转移。我们提出了一个理论模型，可以重现纳米环的吸收光谱并量化纳米环和中心染料之间的激子耦合，从而解释有效的能量转移并证明与结构相关的自然光捕获系统的相似性。
• The influence of selected O-alkyl derivatives of cyclodextrins on the enzymatic decomposition of l-tryptophan by l-tryptophan indole-lyase
  作者：Tomasz Gubica、Elżbieta Winnicka、Andrzej Temeriusz、Marianna Kańska

  DOI：10.1016/j.carres.2008.11.004

  日期：2009.2

  process, both competitive and non-competitive. The competitive inhibition is connected with the formation of inclusion complexes between cyclodextrins and L-tryptophan, related to the geometry of these complexes. The mechanism of the non-competitive inhibition is not so evident; it could be related to the formation of the cyclodextrin complexes on the surface of the enzyme, leading to the change in the

  环糊精的一系列O-烷基衍生物：heksakis [2,3,6-tri-O-（2'-甲氧基乙基）]-α-环糊精；heksakis（2,3-di-O-methyl）-alpha-cyclodextrin; 七（2,3-二-O-甲基）-β-环糊精; heksakis [2，3-二-O-甲基-6-O-（2'-甲氧基乙基）]-α-环糊精；七[2,3-二-O-甲基-6-O-（2'-甲氧基乙基）]-β-环糊精; 合成了heksakis [2,3-二-O-（2'-甲氧基乙基）]-α-环糊精和庚基[2,3-di-O-（2'-甲氧基乙基）]-β-环糊精。检查所得物质的纯度和组成。在L-色氨酸的酶促分解过程中，已经研究了上面列出的环糊精衍生物以及（2-羟丙基）-α-环糊精和（2-羟丙基）-β-环糊精，这两种市售衍生物。通过L-色氨酸吲哚裂解酶。已经发现，每种环糊精衍生物均引起竞争性和非竞争性酶过程的抑制。竞争抑
• A built-in route leading to a self-inclusion complex of 6^A,6^B-(bis-<i>O-p</i>-allyloxyphenyl)hexakis(2,3-di-<i>O</i>-methyl)-α-cyclodextrin
  作者：Zhen Chen、Jerald S. Bradshaw、Yoichi Habata、Milton L. Lee

  DOI：10.1002/jhet.5570340342

  日期：1997.5

  Hexakis(2,3-di-O-methyl)-α-cyclodextrin was treated with 2,4-dimethoxybenzene-1,5-disulfonyl chloride to give 6A,6B-di-O-sulfonated product 5 in only a 3.0% yield. When treated with sodium p-allyloxyphenoxide, 5 gave 6A,6B-(bis-O-p-allyloxyphenyl)hexakis(2,3-di-O-methyl)-α-cyclodextrin (6) in a 57% yield. A careful 1H nmr analysis of 6 shows that one of the allyloxphenyl groups is in the α-cyclodextrin

  用2,4-二甲氧基苯-1,5-二磺酰氯处理六（2,3-二-O-甲基）-α-环糊精，仅以3.0就得到6 A，6 B-二-O-磺化产物5 ％ 屈服。当与钠处理p -allyloxyphenoxide，5得到6-甲，6乙- （双- ø - p -allyloxyphenyl）六（2,3-二- ø -甲基），产率为57％-α环糊精（6）。小心1对6的H nmr分析表明，烯丙基氧苯基之一在α-环糊精腔中。这是由修饰的α-环糊精形成的第一个分子内复合物。分子模型被用来解释实验事实。提出了一种新颖的内在途径，该途径可导致自包涵体的α-环糊精复合物。
• Cyanoethylation of cyclodextrin derivatives
  作者：Ramprasad Ghosh、Moulimala Bhowmick、Ping Zhang、Chang-Chun Ling

  DOI：10.1139/cjc-2015-0379

  日期：2016.4

  The synthesis of novel cyanoethylated cyclodextrin derivatives from previously prepared intermediates is described. It was found the alcohols at the primary face of cyclodextrins readily react to add to acrylonitrile, but similar additions from hydroxyl groups of the secondary face appear to be more difficult. The obtained cyanides could be reduced to form the corresponding amines.

  描述了从先前制备的中间体合成新型氰乙基化环糊精衍生物。发现在环糊精的主面上的醇很容易反应添加到丙烯腈中，但从第二面上的羟基进行类似的添加似乎更困难。得到的氰化物可以还原形成相应的胺。
• Synthetic K ⁺ Channels Constructed by Rebuilding the Core Modules of Natural K ⁺ Channels in an Artificial System
  作者：Pengyang Xin、Linqi Xu、Wenpei Dong、Linlin Mao、Jingjing Guo、Jingjing Bi、Shouwei Zhang、Yan Pei、Chang‐Po Chen

  DOI：10.1002/anie.202217859

  日期：2023.2.13

  Rebuilding the core modules of natural K+ channels in an artificial system has led to a biomimetic K+ channel. This channel possesses similar structural features as the natural version, which enables it to replicate the transport behavior and biological function of natural K+ channels.

  在人工系统中重建天然 K +通道的核心模块导致了仿生 K +通道。该通道具有与天然版本相似的结构特征，使其能够复制天然 K +通道的传输行为和生物学功能。