O1,O3-bis(3-phthalimidopropyl)-p-tert-butylcalix[4]arene | 757236-49-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: O1,O3-bis(3-phthalimidopropyl)-p-tert-butylcalix[4]arene
• 英文别名: bis(3-phthalimidopropoxy)calix[4]arene；2,2'-(((15,35,55,75-tetra-tert-butyl-32,72-dihydroxy-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-12,52-diyl)bis(oxy))bis(propane-3,1-diyl))bis(isoindoline-1,3-dione)；bis(3-N-phthalimidopropyl)-p-terf-butylcalix[4]arene；5,11,17,23-tetra-tert-butyl-25,27-bis(phthalimidopropoxy)calix[4]arene-26,28-diol；2-[3-[[5,11,17,23-Tetratert-butyl-27-[3-(1,3-dioxoisoindol-2-yl)propoxy]-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]isoindole-1,3-dione
• CAS: 757236-49-0
• 化学式: C₆₆H₇₄N₂O₈
• 分子量: 1023.32
• InChiKey: FBKJDDKARUBVBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  76
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  O1,O3-bis(3-phthalimidopropyl)-p-tert-butylcalix[4]arene 在 肼 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 1-[3,5-Bis(trifluoromethyl)phenyl]-3-[3-[[27-[3-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]propoxy]-5,11,17,23-tetratert-butyl-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl]thiourea
  参考文献：
  名称：

  Proline–calixarene thiourea host–guest complex catalyzed enantioselective aldol reactions: from nonpolar solvents to the presence of water

  摘要：

  A proline-calix[4]arene thiourea host-guest complex catalyzed intermolecular aldol reaction of aromatic aldehydes with cyclohexanone has been developed. The anti-configured products were obtained in good yields and with high enantioselectivities. The reaction is proposed to work via a modified Houk-List model, where the carboxylate part of the praline constitutes as a supramolecular system with the thiourea. The outcome of the study indicates the influence of the calix[4]arene thiourea on both the reactivity and selectivity in a non-polar reaction medium, even in the presence of water at moderate temperatures. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.01.015
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 77.5h， 生成 O1,O3-bis(3-phthalimidopropyl)-p-tert-butylcalix[4]arene
  参考文献：
  名称：

  新型6-哌啶-1-基嘧啶-2,4-二胺3-氧化物取代的杯[4]芳烃作为水性样品中Cu 2+的高选择性和灵敏荧光传感器

  摘要：

  在这项研究中，我们通过形成两个脲键，将两个米诺地尔分子连接在杯[4]芳烃环的下边缘，从而设计并合成了一种新颖的Cu 2+阳离子灵敏荧光传感器。该化学传感器可以通过荧光发射的显着下降来选择性地识别含有5％H 2 O的EtOH中的Cu 2+。通过HRMS，1 H NMR，13 C NMR和FT-IR确定靶分子的结构。

  DOI：

  10.1016/j.tetlet.2020.151658

文献信息

• Cavity-containing supramolecular gels as a crystallization tool for hydrophobic pharmaceuticals
  作者：Lena Kaufmann、Stuart R. Kennedy、Christopher D. Jones、Jonathan W. Steed

  DOI：10.1039/c6cc04037c

  日期：——

  We present two approaches to low-molecular-weight supramolecular gels bearing hydrophobic cavities based on calixarene-containing building blocks. Gels are formed by a calixarene based tetrahydrazide gelator or a co-gel of a...

  我们提出了两种方法，以低分子量超分子凝胶为基础，这些凝胶具有基于含杯芳烃的结构单元的疏水腔。凝胶是由基于杯芳烃的四酰肼胶凝剂或硅藻土的共凝胶形成的。
• Synthesis of new chiral calix[4]arene thiourea derivatives for enantiomeric recognition of carboxylate anions
  作者：Selahattin Bozkurt、Mustafa Burak Turkmen、Cengiz Soykan

  DOI：10.1007/s10847-015-0579-7

  日期：2016.2

  thiourea derivatives has been reported. The enantioselectivity of chiral receptors was investigated by using UV–Vis spectroscopy. All the chiral calix[4]arene derivatives exhibited certain chiral recognition towards the enantiomers of α-hydroxy isovaleric acid (HIVA), mandelic acid (MA), 2-chloromandelic acid (2-ClMA) and N-Boc-alanine (N-BocAl). The receptors with hydrogen bonding sites and aromatic groups

  摘要 氨基酸和羧酸化合物的对映体识别研究具有重要意义，因为这些化合物是生物分子的基本组成部分。这些化合物的对映体识别和分离是超分子化学的主要课题之一，因为它们是生物分子的基本组成部分，并且其中一些已知具有有效的生物活性。本研究报道了新型手性杯[4]芳烃硫脲衍生物的合成。通过使用紫外-可见光谱研究了手性受体的对映选择性。所有手性杯[4]芳烃衍生物对α-羟基异戊酸(HIVA)、扁桃酸(MA)、2-氯扁桃酸(2-ClMA)和N-Boc-丙氨酸(N-觯）。具有氢键位点和芳族基团的受体显示出相当高的立体选择性。作为手性受体，杯[4]芳烃2-羟基-1,2二苯醚硫脲衍生物在25°C下对2-氯扁桃酸（高达KR/KS = 2.80）具有对映体区分能力。还从热力学的角度讨论了对客体的对映体识别能力。
• 1,3-Alternate calix[4]arenes, selectively functionalized by amino groups
  作者：Crenguta Danila、Michael Bolte、Volker Böhmer

  DOI：10.1039/b414173c

  日期：——

  synthesize calix[4]arenes which are fixed in the 1,3-alternate conformation and substituted selectively by amino groups. These derivatives are useful starting materials for the attachment of various groups via amide bonds, as demonstrated by several examples, but may be converted also to ureas, imides or azomethines. Four amino groups may be attached to the narrow rim via(several) methylene groups as spacer

  描述了合成杯盖[4]芳烃的一般策略，这些芳烃固定在1,3-交替构象中并被氨基选择性取代。这些衍生物是有用的起始原料，用于通过酰胺键连接各种基团，如几个实例所示，但也可以转化为脲，酰亚胺或偶氮甲碱。四个氨基可以通过（几个）亚甲基作为间隔基通过ω-溴邻苯二甲酰亚胺或ω-溴腈的O-烷基化连接到狭窄的边缘。从所得的四醚中，通过用肼裂解或通过水解获得氨基官能团，从而允许分子两侧的选择性官能化（酚单元A，C相对于B，D）。通过各自的叔丁基杯[4]芳烃衍生物的ipso-硝化和随后的还原反应，在宽边缘引入氨基官能团。1,3-二醚的选择性ipis硝化，然后用烯丙基溴进行O-烷基化，得到1,3-交替构象的四醚，烯丙基和硝基的氢化（一步），氨基的保护作用如下：邻苯二甲酰亚胺，然后剩余的叔丁基苯酚环进行异丙基硝化，可以再次区分分子的两面（A，C与B，D单元）。Boc-酸酐使宽边四胺以1,3-交替构型与Boc-酸酐
• Impact of Tetracationic Calix[4]arene Conformation—from Conic Structure to Expanded Bolaform—on Their Antibacterial and Antimycobacterial Activities
  作者：Maxime Mourer、Raphaël E. Duval、Patricia Constant、Mamadou Daffé、Jean‐Bernard Regnouf‐de‐Vains

  DOI：10.1002/cbic.201800609

  日期：2019.4

  The four possible conformers of a new tetrakisguanidino calix[4]arene thought to interact deleteriously with bacterial membranes have been synthesized, characterized, and evaluated for their in vitro cytotoxicity and antibacterial activity against various reference Gram-negative and Gram-positive bacteria, as well as Mycobacterium tuberculosis. It appears that reversal of at least one phenolic unit

  合成，表征并评估了新的四kisguanidino calix [4]芳烃与细菌膜有害相互作用的四种可能的构象异构体，并对它们对各种参考革兰氏阴性和革兰氏阳性细菌的体外细胞毒性和抗菌活性进行了评估。如结核分枝杆菌。似乎至少一个酚醛单元的逆转导致它们活性的明显增加。这可以归因于向着弓形结构的进化，该结构能够与细菌膜更深层地相互作用。实际上，1，3-交替构象异构体16表现出最佳的抗菌活性（对金黄色葡萄球菌的MIC ＜1.0μgmL-1）。此外，有16种药物对结核分枝杆菌的耐异烟肼菌株（MIC = 1.2μgmL-1）具有很好的抗菌活性，与最低的细胞毒性相关，因此使其成为该系列中最有效的化合物；这可能会为抗感染药物开发领域开辟新的研究方法，以满足当前的巨大需求。
• Synthesis of new calix[4]arene derivatives and evaluation of their cytotoxic activity
  作者：Mehmet Oguz、Ayse Yildirim、Irem Mukaddes Durmus、Serdar Karakurt、Mustafa Yilmaz

  DOI：10.1007/s00044-021-02813-7

  日期：2022.1

  the dihydrazide (3a and 3b) and diamino propyl (6a and 6b) derivatives of p-tert-butylcalix[4]arene and calix[4]arene were synthesized. Then the L-proline methyl ester substituted chlorocyclopropenium was reacted with the calix[4]arene derivatives (3a, 3b, 6a, and 6b) at room temperature in CH2Cl2 to obtain calix[4]arene superbase derivatives (4a, 4b, 7a, and 7b) in 75%, 60%, 70%, and 55% yield, respectively

  Since calixarenes are more easily synthesized and functionalized than other supramolecules, they are compounds of interest in organic chemistry. In this study, the dihydrazide (3a and 3b) and diamino propyl (6a and 6b) derivatives of p-tert-butylcalix[4]arene and calix[4]arene were synthesized. Then the L-proline methyl ester substituted chlorocyclopropenium was reacted with the calix[4]arene derivatives