6^A-deoxy-6^A-propynamido-β-cyclodextrin | 218596-55-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6^A-deoxy-6^A-propynamido-β-cyclodextrin
• 英文别名: propynamido-β-cyclodextrin；N-[[(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)-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30,35-hexakis(hydroxymethyl)-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]nonatetracontan-5-yl]methyl]prop-2-ynamide
• CAS: 218596-55-5
• 化学式: C₄₅H₇₁NO₃₅
• 分子量: 1186.04
• InChiKey: RWZVTHRXWRFMEU-MKWHQSKQSA-N

物化性质

• 密度：
  1.601±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -14.5
• 重原子数：
  81
• 可旋转键数：
  8
• 环数：
  21.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  563
• 氢给体数：
  21
• 氢受体数：
  35

反应信息

• 作为反应物：
  描述：

  6^A-deoxy-6^A-propynamido-β-cyclodextrin 、 1-ethoxycarbonylmethyl-4-(4'-pyridyl)pyridinium bromide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以35%的产率得到N-(6^A-deoxy-β-cyclodextrin-6^A-yl)-1-(aminocarbonyl)-3-(ethoxycarbonyl)-7-pyridin-4-ylindolizine
  参考文献：
  名称：

  联吡啶鎓与丙基-β-环糊精的1，3-偶极环加成反应。新型荧光β-环糊精的区域特异性合成

  摘要：

  研究了联吡啶鎓与电子缺陷的丙酰胺基-β-环糊精的1,3-偶极环加成反应。该反应导致新型荧光β-环糊精的区域特异性形成。新的荧光团系统的光谱学特征是其最大吸收和发射量以及其量子产率。

  DOI：

  10.1016/j.tet.2003.12.006
• 作为产物：
  描述：

  4-nitrophenyl propiolate 、 单-6-O-氨基-Β-环糊精 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以80%的产率得到6^A-deoxy-6^A-propynamido-β-cyclodextrin
  参考文献：
  名称：

  联吡啶鎓与丙基-β-环糊精的1，3-偶极环加成反应。新型荧光β-环糊精的区域特异性合成

  摘要：

  研究了联吡啶鎓与电子缺陷的丙酰胺基-β-环糊精的1,3-偶极环加成反应。该反应导致新型荧光β-环糊精的区域特异性形成。新的荧光团系统的光谱学特征是其最大吸收和发射量以及其量子产率。

  DOI：

  10.1016/j.tet.2003.12.006

文献信息

• Synthesis of a new fluorinated fluorescent β-cyclodextrin sensor
  作者：Neculai Catalin Lungu、Adrien Dépret、François Delattre、Georgiana G Surpateanu、Francine Cazier、Patrice Woisel、Pirouz Shirali、Gheorghe Surpateanu

  DOI：10.1016/j.jfluchem.2005.01.006

  日期：2005.3

  The synthesis of a new fluorescent sensor incorporating a fluorinated indolizine unit bound to 6-amino-β-cyclodextrin by two different synthetic ways is described. Its sensing ability toward adamantanol has been demonstrated.

  描述了一种新的荧光传感器的合成，该传感器结合了通过两种不同的合成方式与6-氨基-β-环糊精结合的氟化吲哚嗪单元。已经证明了其对金刚烷醇的感测能力。
• Reversal of Regioselectivity and Enhancement of Rates of Nitrile Oxide Cycloadditions through Transient Attachment of Dipolarophiles to Cyclodextrins
  作者：Lorna Barr、Stephen F. Lincoln、Christopher J. Easton

  DOI：10.1002/chem.200600627

  日期：2006.11.15

  4-tert-butylbenzonitrile oxide with acrylic acid, methacrylic acid, and crotonic acid is also altered by formation of the corresponding cyclodextrin esters, by factors of 500, >10, and >100, respectively. The rates of cycloaddition are also increased by up to 475 times, and in these cases the products of cycloaddition are readily released from the cyclodextrin through ester hydrolysis. Incorporating these

  腈氧化物与单取代的亲脂性物质如丙酰胺的反应通常按比例提供80％或更多的3，5-二取代的环加合物。相比之下，6（A）-脱氧-6（A）-丙酰胺基-β-环糊精与4-叔丁基苄腈氧化物和4-苯基苄腈氧化物的反应可提供> 90％的溶液和约85％的相应3,4-二取代异恶唑分别。除了逆转区域选择性外，环糊精还增加了这些环加成的速率。对于环糊精优选的环加合物的生产，加速的程度高达三个数量级以上，但是甚至给出给出较不优选的区域异构体的反应速率也增加了。使用6（A）-脱氧-6（A）-丙酰胺基-β-环糊精，由于酰胺键不容易裂解，因此不容易将环加合物与环糊精分离。相比之下，4-叔丁基苄腈氧化物与丙烯酸，甲基丙烯酸和巴豆酸的环加成反应的区域选择性也通过形成相应的环糊精酯而改变，分别为500，> 10和> 100。环加成的速率也增加了多达475倍，在这些情况下，环加成的产物很容易通过酯水解从环糊精中释放出来。将这些过程
• SYNTHESIS OF NEW FLUORESCENT β-CYCLODEXTRIN SENSOR
  作者：Mathieu Becuwe、François Delattre、Georgiana G. Surpateanu、Francine Cazier、Patrice Woisel、Guillaume Garçon、Pirouz Shirali、Gheorghe Surpateanu

  DOI：10.1515/hc.2005.11.3-4.355

  日期：2005.1

  The synthesis of a new fluorescent sensor incorporating a fluoro pyridine indolizinic unit and a ßcyclodextrin fragment by two different synthetic ways is described.

  描述了通过两种不同的合成方式合成了一种新的荧光传感器，该传感器包含一个氟吡啶 indolizinic 单元和一个 ß环糊精片段。
• β-Cyclodextrin as a Scaffold for Supramolecular Chemistry, To Reverse the Regioselectivity of Nitrile Oxide Cycloadditions
  作者：Adam G. Meyer、Christopher J. Easton、Stephen F. Lincoln、Gregory W. Simpson

  DOI：10.1021/jo9817321

  日期：1998.11.1

  beta-Cyclodextrin has been used as a molecular scaffold, whereby tethering dipolarophiles to the cyclodextrin and then allowing preassociation of the modified cyclodextrins with aromatic nitrile oxides, as host-guest complexes, controls the relative orientations of the dipoles and the dipolarophiles in their cycloadditions. In this manner it has been possible to reverse the usual regioselectivity of cycloadditions of nitrile oxides, as illustrated by reactions with a terminal alkene, a terminal alkyne, and a 1,2-disubstituted alkene. For example, iii aqueous solution, 4-tert-butylbenzonitrile oxide reacted with 6(A)-deoxy-6(A)-propynamido-beta-cyclodextrin to give the corresponding 4- and 5-substituted isoxazoles, in a 15:1 ratio. With DMF as the solvent, to reduce the extent of host-guest complexation, the product ratio was 1:1.5. The role of complexation in these reactions is also demonstrated by contrasting these results with that of the reaction of the nitrile oxide with methyl propynoate, which afforded only the 5-substituted cycloaddition product. Molecular recognition by the cyclodextrin scaffolds was demonstrated through treatment of 4-tert-butylbenzonitrile oxide with an equimolar mixture of 6(A)-deoxy-6(A)-prapynamido-beta-cyclodextrin and methyl propynoate, in aqueous solution, which gave only the cycloadducts from reaction of the cyclodextrin dipolarophile.