2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol | 2726-11-6

• 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: 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol
• 英文别名: 2-((6-(2-hydroxybenzylamino)hexylamino)methyl)phenol；N,N-hexamethylenediaminebis(o-hydroxybenzylamine)；N,N'-Bis-(2-hydroxybenzyl)-hexamethylenediamine；2-[[6-[(2-hydroxyphenyl)methylamino]hexylamino]methyl]phenol
• CAS: 2726-11-6
• 化学式: C₂₀H₂₈N₂O₂
• 分子量: 328.455
• InChiKey: DHSAOPPPTOFPHV-UHFFFAOYSA-N

物化性质

• 沸点：
  504.3±45.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.5
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2,4,4,6,6,8,8-八氯-2,2,4,4,6,6,8,8-八氢-1,3,5,7,2,4,6,8-四氮杂四磷杂环辛烯 、 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 以4%的产率得到
  参考文献：
  名称：

  Phosphorus–Nitrogen Compounds. Part 24. Syntheses, Crystal Structures, Spectroscopic and Stereogenic Properties, Biological Activities, and DNA Interactions of Novel Spiro-ansa-spiro- and Ansa-spiro-ansa-cyclotetraphosphazenes

  摘要：

  The reactions of octachlorocyclotetraphosphazene, N4P4Cl8, with N2O2 donor-type aminopodands (1a, 1b, 1g, and 1h) afforded two kinds of derivatives, namely, spiro-ansa-spiro (sas) (2a, 2b, 2g, and 2h) and ansa-spiro-ansa (asa) (3a and 3b) phosphazenes. The partly substituted sas phosphazenes (2a and 2b) reacted with excess pyrrolidine and morpholine in tetrahydrofuran to produce the tetrapyrrolidino (2c and 2d) and morpholino (2e and 2f) derivatives. The reactions of the asa phosphazenes (3a and 3b) with excess pyrrolidine and morpholine produced gem-2-trans-6-dichloropyrrolidinophosphazenes (3c and 3d) and -morpholinophosphazenes (3e and 3f). However, the fully substituted products were not obtained in these solvents. In addition, the expected fully substituted compound was not obtained from the reaction of 3a with excess pyrrolidine by standard or microwave-assisted methods. The reaction of the long-chain starting compound (1g) with N4P4Cl8 gave sas (2g) and the interesting 2,6-ansa-spiro-bicyclo product (bicyclo-2,6-as; 4g), while the reaction of 1h with N4P4Cl8 yielded only sas (2h). The structural investigations of the compounds were verified by elemental analyses, mass spectrometry, Fourier transform infrared, and DEPT, HSQC, HMBC, H-1, C-13, and P-31 NMR techniques. The crystal structures of 2b, 3a, 3b, 3e, and 4g were determined by X-ray crystallography. Compounds 2a-2h, 3a-3f, and 4g had two stereogenic P atoms. Compound 3b had one enantiomer according to the Flack parameter, and 3f was a racemic mixture, as shown by chiral high-performance liquid chromatography and chiral-solvating-agent, (R)-(+)-2,2,2-trifluoro-1-(9'-anthryl)ethanol, experiments. Furthermore, compounds 2a, 2c, and 2d exhibited weak antibacterial activity against (G+) bacterium, and 3c and 3d displayed moderate antifungal activity against Candida tropicalis. Gel electrophoresis data demonstrated that 2e, 3c, and 3e promoted the formation of DNA cleavage. The prevention of BamHI digestion by 2a-2f and 3a-3f, except 2b and 2e, disclosed binding with GG nucleotides in DNA.

  DOI：

  10.1021/ic3017134
• 作为产物：
  描述：

  N,N’-双(亚水杨基)-1,6-己烷二胺 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol
  参考文献：
  名称：

  席夫和Y沸石中包裹的席夫碱和四氢席夫碱的二氧钒钒（V）络合物，用于苯乙烯的好氧氧化

  摘要：

  将一系列席夫碱和四氢席夫碱的二氧钒钒（V）配合物包封到Y型沸石的超笼中，并通过X射线衍射，SEM，N 2表征吸附/解吸，红外光谱，紫外可见光谱，ICPAES，对分布函数（PDF）和X射线吸收近边缘结构（XANES）测量。通过柔性配体方法实现包封，其中首先将过渡金属阳离子离子交换成Y型沸石，然后与配体络合。筛选了二氧钒交换沸石，包裹在Y型沸石中的二氧钒络合物以及未包裹的均相对应物，作为在温和条件下进行好氧氧化苯乙烯的催化剂。发现在大多数情况下，包封的复合物显示出比其各自的未包封的对应物更好的活性。所有包封的二氧钒钒四氢-席夫碱配合物在需氧氧化苯乙烯中显示出比其相应席夫碱配合物更高的活性。

  DOI：

  10.1134/s0023158417030053
• 作为试剂：
  描述：

  水杨醛 、 1,6-己二胺 在 镍 异丙醇 、 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol 作用下， 以 异丙醇 为溶剂， 25.0~75.0 ℃ 、1215.8 MPa 条件下， 生成 2,2′-[1,6-hexanediylbis(iminomethanediyl)]diphenol
  参考文献：
  名称：

  Curable epoxide resin mixtures

  摘要：

  可治疗混合物包含（a）平均每个分子具有多于一个环氧基团的多环氧化合物和（b）含有羟基的二胺，其具有Ia或Ib的一般式##STR1##其中R是具有2至16个碳原子的烷基基团，具有7至12个碳原子的芳烷基基团，具有6至16个碳原子的芳基基团，具有6至12个碳原子的环状脂肪基基团或包含至少一个N、O或S原子的链或环状基团，R.sub.1是氢原子，卤素原子或具有1至4个碳原子的烷基基团，并且在Ia公式中，两个OH基团位于相对于亚甲基基团的邻位或对位，混合物中含有0.5至1.5当量的活性氢原子，这些原子与含有羟基的二胺中的氮和氧键合，每1当量环氧基团。

  公开号：

  US04129556A1

文献信息

• Salen and tetrahydrosalen derivatives act as effective inhibitors of the tumor-associated carbonic anhydrase XII—A new scaffold for designing isoform-selective inhibitors
  作者：Simone Carradori、Celeste De Monte、Melissa D’Ascenzio、Daniela Secci、Gulsah Celik、Mariangela Ceruso、Daniela Vullo、Andrea Scozzafava、Claudiu T. Supuran

  DOI：10.1016/j.bmcl.2013.10.026

  日期：2013.12

  possess metal-chelating properties and have been used as ligands in organic synthesis and as scaffolds for developing therapeutic agents. Fourteen such compounds were synthesized in order to explore their ability to inhibit the zinc enzyme carbonic anhydrase (CA, EC 4.2.1.1). Human (h) isoforms hCA I, hCA II, hCA IX and hCA XII were included in the investigation. Several aliphatic and aromatic spacers

  Salen和四氢salen衍生物具有金属螯合性能，并已用作有机合成中的配体和用作开发治疗剂的支架。为了探索其抑制锌酶碳酸酐酶的能力（CA，EC 4.2.1.1），合成了14种这样的化合物。人（h）异构体hCA I，hCA II，hCA IX和hCA XII包括在研究中。为了探索设计CA抑制剂的多样化化学空间，在其分子中掺入酚和多胺片段，CA抑制剂的两个螯合基团之间引入了几个脂族和芳族间隔基。其中一些化合物在低微摩尔-纳摩尔范围内显示出CA抑制活性，并且对低氧性肿瘤hCA XII中过表达的同工型具有明显的选择性。
• <i>N</i> ‐alkyl imidazole‐based homonuclear coordination complex as a neutral organocatalyst for the faster and efficient construction of 3,4‐dihydro‐2 <i>H</i> ‐1,3‐oxazine scaffold
  作者：Ayhan Yıldırım、Mustafa Göker

  DOI：10.1002/aoc.6425

  日期：2021.12

  N-hexadecylimidazole ligand was used for the first time as a highly efficient homogeneous neutral organocatalyst for the synthesis of 3,4-dihydro-2H-1,3-benzoxazine monomers. Therefore, N-alkyl or N-aryl substituted, both mono-benzoxazine and bis-benzoxazine, were successfully synthesized (21 examples) via Mannich-type condensation reactions. Effortlessly obtaining the pure product with high yields

  在目前的工作中，包括 Zn (II) 和N-十六烷基咪唑配体的同核配位络合物首次用作合成 3,4-二氢-2 H -1,3-苯并恶嗪单体的高效均相中性有机催化剂. 因此，通过曼尼希型缩合反应成功合成了N-烷基或N-芳基取代的单苯并恶嗪和双苯并恶嗪（21 个实例）。毫不费力地以高收率和短反应时间获得纯产物，使该方法比现有的常见苯并恶嗪合成方法更有用和更有利。
• Design, Spectral analysis, DFT calculations, antimicrobial, anti-TB, antioxidant activity and molecular docking studies of novel bis-benzoxazines with cytochrome c peroxidase
  作者：G.Y. Nagesh、Mohammad Javeed、Jeelan N. Basha、K. Prashantha、R. Nithin、P.R. Thanushree、S. Vivekananda、Siri S. Gowda、H.B. Punarva、S.M. Basavarajaiah

  DOI：10.1016/j.molstruc.2022.132977

  日期：2022.8

  preferable 1,2-bis(6-substituted-2H-benzo[e][1,3]oxazin-3(4H)-yl)ethanes, 5a-h formed when the compounds 4a-h undergo an internal Mannich reaction with formaldehyde. Different spectroscopic methods prove the formation of all the compounds. The compounds 3g, 4g, 5c, and 5g showed excellent antibacterial activity against S. aureus, E. coli, S. Typhi, and B. subtilis, antifungal activity against A. flavus

  我们在此报告了通过取代水杨醛和烷基二胺有效合成对称双苯并恶嗪。取代的水杨醛( 1a-d )和烷基二胺 (2a-b)反应合成席夫碱 3a-h。 这些化合物在无水甲醇中用 NaBH4 还原得到 2,2'-((烷基-1,2-二基双(氮杂二基))双(亚甲基))二取代苯酚，  4a-h  ，收率良好。优选的1,2-双(6-取代-2H-苯并[ e ][1,3]oxazin - 3( 4H )-基)乙烷，5a-h 当化合物 4a-h 与甲醛发生内部曼尼希反应。不同的光谱方法证明了所有化合物的形成。化合物3g、 4g 、5c和5g对金黄色葡萄球菌、大肠杆菌、伤寒杆菌和枯草芽孢杆菌具有优异的抗菌活性，对黄曲霉、白色念珠菌、黑曲霉、和 C. oxysporum，MIC 值为 6.25 µg/ml，抗结核分枝杆菌活性与标准药物相当。此外，对化合物3b、3c、 3g 、4c、5b和5f的抗氧化活性的研究显示它们具有出色的抗氧化活性。为了理解化合物5e
• Synthesis of Large Macrocycles with Chiral Sulfur Centers via Enantiospecific SuFEx and SuPhenEx Click Reactions
  作者：Yang Chao、Muthusamy Subramaniam、Kayambu Namitharan、Yumei Zhu、Victor Koolma、Zitong Hao、Shikang Li、Yaxin Wang、Ilyos Hudoynazarov、Fedor M. Miloserdov、Han Zuilhof

  DOI：10.1021/acs.joc.3c01656

  日期：2023.11.17

  Here we report the first asymmetric synthesis of large chiral macrocycles with chiral sulfur atoms. Building on stereospecific SuFEx and SuPhenEx click chemistries, this approach utilizes disulfonimidoyl fluorides and disulfonimidoyl p-nitrophenolates─which are efficient building blocks with two chiral sulfur centers, and diphenols to efficiently form novel S–O bonds. Characteristic results include

  在这里，我们报道了具有手性硫原子的大手性大环的首次不对称合成。该方法基于立体特异性 SuFEx 和 SuPhenEx 点击化学，利用二磺酰亚胺酰氟和二磺酰亚胺对硝基酚酸盐，它们是具有两个手性硫中心的高效结构单元，而二酚可有效形成新型 S-O 键。特征结果包括由 21-58 个成员组成的对映体特异性一步合成环，以及通过 X 射线晶体学等对映异构体（R，R 和 S，S）的表征。
• Csaszar, Jozsef, Acta Chimica Hungarica, 1991, vol. 128, p. 255 - 266
  作者：Csaszar, Jozsef

  DOI：——

  日期：——