32,33-Dihydroxy-3-methylidene-15,22-diazapentacyclo[22.7.1.15,13.06,11.026,31]tritriaconta-1(32),5(33),6,8,10,12,24,26,28,30-decaene-14,23-dione | 937242-85-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酰胺类
• 英文名称: 32,33-Dihydroxy-3-methylidene-15,22-diazapentacyclo[22.7.1.15,13.06,11.026,31]tritriaconta-1(32),5(33),6,8,10,12,24,26,28,30-decaene-14,23-dione
• CAS: 937242-85-8
• 化学式: C₃₂H₃₂N₂O₄
• 分子量: 508.617
• InChiKey: POQMZCDEBHCQGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  38
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  32,33-Dihydroxy-3-methylidene-15,22-diazapentacyclo[22.7.1.15,13.06,11.026,31]tritriaconta-1(32),5(33),6,8,10,12,24,26,28,30-decaene-14,23-dione 反应 1.0h， 生成 33-Hydroxy-3-methyl-4-oxa-16,23-diazahexacyclo[23.7.1.13,6.05,14.07,12.027,32]tetratriaconta-1(33),5,7,9,11,13,25,27,29,31-decaene-15,24-dione
  参考文献：
  名称：

  Controllable synthesis, structures of amidecrownophane-type macrocycles and their binding ability toward anions

  摘要：

  Amidecrownophane-type macrocycles with different number of hydroxy groups were prepared in quantitative yields by control of the conditions of thermal reaction with the aim to examine the role of hydroxy groups in anion recognition. It was proved that the hydroxy group played a critical role in anion binding for this type of macrocycles and the anion binding affinity could be tuned by different number of hydroxy groups. Further exploration clarified the presence of intramolecular hydrogen-bonding and exhibited the major effect on their anion binding potential. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.02.019
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 二甲基亚砜 为溶剂， 生成 32,33-Dihydroxy-3-methylidene-15,22-diazapentacyclo[22.7.1.15,13.06,11.026,31]tritriaconta-1(32),5(33),6,8,10,12,24,26,28,30-decaene-14,23-dione
  参考文献：
  名称：

  环烷型大环中羟基与异丁烯链之间的新型分子内可逆反应

  摘要：

  利用异丁烯与环烷芳族羟基的分子内反应，实现了新型的Hg 2+离子诱导的可逆环收缩。过量添加NaBH 4促进了反应的可逆性，这也导致络合。通过UV-VIS吸收，荧光和1 H NMR光谱监测环的收缩和膨胀。当将环的大小从19元环调整为18元时，可以观察到可切换的荧光行为（开-关-开）。这种微调有可能被应用在新的超分子器件的构造中。

  DOI：

  10.1515/chempap-2015-0241

文献信息

• Macrocyclic bis(amidonaphthol)s for anion sensing: tunable selectivity by ring size in proton transfer process
  作者：Wei-tao Gong、Kazuhisa Hiratani、Shim Sung Lee

  DOI：10.1016/j.tet.2008.10.002

  日期：2008.12

  The investigation on anion sensing properties for a series of macrocyclic bis(amidonaphthol)s 3a–3c reveals the significant effects of macrocyclic ring size. Among them, macrocycle 3c with the largest ring size shows F− ion selectivity by causing clear red shift (24 nm) in fluorescence emission after complexation with F−, which results in significant color change of fluorescence from blue to green

  对一系列大环双（氨基酚）3a - 3c的阴离子感测性质的研究揭示了大环环尺寸的显着影响。其中，大环化合物3C具有最大环尺寸描绘了f -通过使荧光发射清晰的红移（24纳米）络合后用氟离子选择性- ，其结果在从蓝色到绿色荧光的显著颜色变化。这对优秀的选择性˚F -离子，可能是由于-OH基团的酸度和F的碱度之间的健身-离子。进一步勘探表示-OH基团的酸性可通过环的大小被调谐到给它辨别在F的亲和力的细微差别的能力-，CH 3 COO - ，和H 2 PO 4 -到-OH质子。
• A convenient and efficient route for the synthesis of amidecrownophanes via 1:1 macrocyclization of di(acid chloride) with diamine derivatives
  作者：Wei-Tao Gong、Kazuhisa Hiratani、Toru Oba、Satoshi Ito

  DOI：10.1016/j.tetlet.2007.02.097

  日期：2007.4

  Four amidecrownophanes 3a–d, including three new compounds 3a, 3c and 3d, were readily prepared through amidation of dicarbonyl dichloride with diamine derivatives without using high-dilution or template conditions and then the tandem Claisen rearrangement. At the macrocyclization step the intramolecular hydrogen bonding of the intermediate might play an important role to give high yields of 1:1 macrocycles

  通过使用二胺衍生物将二氯化二羰基二酰胺酰胺化，无需使用高稀释度或模板条件，然后串联克莱森重排，即可轻松制备出四个酰胺基乌鸦烷3a - d，包括三个新化合物3a，3c和3d。在大环化步骤中，中间体的分子内氢键可能起重要作用，以高收率为1：1的大环。