11-amino-23-hydroxycarbonyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene | 702699-88-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 11-amino-23-hydroxycarbonyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene
• 英文别名: 11-amino-25,27-dihydroxy-26,28-dipropoxycalix[4]arene-23-carboxylic acid；17-Amino-26,28-dihydroxy-25,27-dipropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5-carboxylic acid；17-amino-26,28-dihydroxy-25,27-dipropoxypentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9(27),10,12,15(26),16,18,21,23-dodecaene-5-carboxylic acid
• CAS: 702699-88-5
• 化学式: C₃₅H₃₇NO₆
• 分子量: 567.682
• InChiKey: XAJCTYMRGRBOML-UHFFFAOYSA-N

物化性质

• 沸点：
  800.3±65.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  11-amino-23-hydroxycarbonyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 11-(N-Cbz-L-alanyl)amino-23-(methoxy-L-alanyl)carbonyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene
  参考文献：
  名称：

  Chiral Dimeric Capsules from N,C-Linked Peptidocalix[4]arenes Self-Assembled through an Antiparallel β-Sheetlike Motif

  摘要：

  The first example of a calix[4]arene amino acid is reported. It allowed the synthesis of the novel N,C-linked peptidocalix[4]arenes which self-assemble in low-polarity media to give chiral dimeric capsules held together by an antiparallel beta-sheetlike hydrogen-bonding motif.

  DOI：

  10.1021/ja031511z
• 作为产物：
  描述：

  11-nitro-23-formyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene 在 palladium on activated charcoal sodium chlorite 、 氨基磺酸 、 一水合肼 作用下， 以 乙醇 、 氯仿 、 丙酮 为溶剂， 反应 24.0h， 生成 11-amino-23-hydroxycarbonyl-25,27-dihydroxy-26,28-dipropoxypentacyclo[19.3.1.1^3,7.1^9,13.1^15,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecene
  参考文献：
  名称：

  Chiral Dimeric Capsules from N,C-Linked Peptidocalix[4]arenes Self-Assembled through an Antiparallel β-Sheetlike Motif

  摘要：

  The first example of a calix[4]arene amino acid is reported. It allowed the synthesis of the novel N,C-linked peptidocalix[4]arenes which self-assemble in low-polarity media to give chiral dimeric capsules held together by an antiparallel beta-sheetlike hydrogen-bonding motif.

  DOI：

  10.1021/ja031511z

文献信息

• Self-Assembled Chiral Dimeric Capsules from DifunctionalizedN,C-Linked Peptidocalix[4]arenes: Scope and Limitations
  作者：Laura Baldini、Francesco Sansone、Giovanni Faimani、Chiara Massera、Alessandro Casnati、Rocco Ungaro

  DOI：10.1002/ejoc.200700943

  日期：2008.2

  condensation reaction. The tetrapropoxycalix[4]arene pseudopeptide 33 shows conformational and self-assembly properties quite different to those of the dipropoxy derivatives 12–21. The observed differences are explained on the basis of the different conformational flexibilities of the two calix[4]arene scaffolds. Calixarene 5 is more rigid than 27 thanks to the presence of two OH groups at the lower (narrow) rim

  在本文中，我们报告了上（宽）边缘杯[4]芳烃氨基酸 5 和 27 的第一个例子的合成，以及 N,C 连接肽杯的构象、自组装和分子包含特性 [4] ]芳烃。虽然二丙基衍生物 5 很容易进行肽合成，从而获得一个小的杯 [4] 芳烃假肽 12-21 库，但四丙氧基化合物 27 优先提供上缘桥接衍生物（例如，28），其通过分子内形成缩合反应。四丙氧基杯[4]芳烃假肽33显示出与二丙氧基衍生物12-21完全不同的构象和自组装特性。观察到的差异是基于两种杯[4]芳烃支架的不同构象灵活性来解释的。杯芳烃 5 比 27 更刚性，这要归功于在较低（窄）边缘存在两个 OH 基团，这些 OH 基团与强分子内氢键有关。只有肽杯[4]芳烃 12-21 而不是 33 形成氢键二聚体胶囊，其中两个大环彼此面对面靠近并相对于另一个旋转 180°，以允许之间的氢键互补相互作用的肽链，在某些情况下 (17-19)，形成一个反平行的
• Solid-phase synthesis of linear and cyclic peptides containing a calix[4]arene amino acid
  作者：Laura Baldini、Francesco Sansone、Federico Scaravelli、Chiara Massera、Alessandro Casnati、Rocco Ungaro

  DOI：10.1016/j.tetlet.2009.02.198

  日期：2009.7

  Solid-phase synthesis is used to obtain new linear and cyclic N,C-linked peptidocalixarenes. The synthetic strategy allows, for the first time, the condensation of a calix[4]arene amino acid during the stepwise elongation sequence of the peptide. An important role is played by the lower rim functionalization of the calixarene since it modulates the flexibility of the calixarene scaffold and the conformational

  固相合成用于获得新的线性和环状N，C连接的肽杯芳烃。合成策略首次允许在肽的逐步延伸序列中杯[4]芳烃氨基酸的缩合。杯芳烃的较低边缘官能化起重要作用，因为它调节了杯芳烃支架的柔韧性和所得非天然肽的构象性质。
• Chiral Dimeric Capsules from <i>N</i>,<i>C</i>-Linked Peptidocalix[4]arenes Self-Assembled through an Antiparallel β-Sheetlike Motif
  作者：Francesco Sansone、Laura Baldini、Alessandro Casnati、Elisa Chierici、Giovanni Faimani、Franco Ugozzoli、Rocco Ungaro

  DOI：10.1021/ja031511z

  日期：2004.5.1

  The first example of a calix[4]arene amino acid is reported. It allowed the synthesis of the novel N,C-linked peptidocalix[4]arenes which self-assemble in low-polarity media to give chiral dimeric capsules held together by an antiparallel beta-sheetlike hydrogen-bonding motif.