3-(N-ferrocenylmethylamino)-1-propanol | 326477-84-3

• 英文名称: 3-(N-ferrocenylmethylamino)-1-propanol
• CAS: 326477-84-3
• 化学式: C₁₄H₁₉FeNO
• 分子量: 273.158
• InChiKey: WODWHUJLLVPKQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  3-(N-ferrocenylmethylamino)-1-propanol 在 sodium hydride 作用下， 生成 sodium 3-(N-ferrocenylmethylamino)-1-propanoxide
  参考文献：
  名称：

  磷-氮化合物。第 65 部分。新型 diansa-spiro-cyclotetraphosphazenes：合成、表征、生物活性和电化学特性，以及染料敏化太阳能电池制造研究

  摘要：

  在本研究中，发现八氯环四磷腈 N 4 P 4 Cl 8（四聚体，OCCP，1）与 3-（N-二茂铁基甲基氨基）-1-丙氧基钠 ( L1 ) 的取代反应生成化合物2,4 -ansa -( 2 ) 和螺-( 2 ) 环四磷腈衍生物。起始的六氯-2-顺式-4-二氯-单二茂铁基-ansa-(N/O)环四磷腈( 2 )分别与N 2 O 2供体型氨基足的二钾盐(KOPhCH 2NH) 2 R [R = (CH 2 ) n , n = 2 ( L2 ) 和n = 3 ( L3 )]，生产单二茂铁基- 2,4-ansa -6,8-ansa-spirocyclotetraphosphazenes ( dias ; 3和4 )。两种产物均通过柱色谱纯化，并使用 ESI-MS、FTIR、1 H、13 C 和31 P NMR 光谱数据确认其结构。此外，通过单晶X射线衍射阐明了4的分子和晶体结构。化合物4有四个不同的手性

  DOI：

  10.1039/d2nj03001b
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3-(N-ferrocenylmethylamino)-1-propanol
  参考文献：
  名称：

  通过金属自由基 C-H 烷基化构建五元环结构的对映选择性自由基环化

  摘要：

  自由基环化代表了构建环状结构的强大策略。传统的自由基环化以自由基加成为关键步骤，需要使用不饱和底物。在金属自由基催化概念的指导下，通过开发基于Co(II)的系统，展示了一种可以使用饱和CH底物的不同自由基环化模式，该系统用于催化活化脂肪族重氮化合物，以实现各种C(sp3)的对映选择性自由基烷基化)-H键。它可以有效构建手性吡咯烷和其他有价值的五元环状化合物。这种自由基环化的替代策略提供了一种新的逆合成范例，通过 CH 和 C=O 元素的结合形成 CC 键，从容易获得的开链醛制备五元环状分子。

  DOI：

  10.1021/jacs.8b01662

文献信息

• Phosphorus-nitrogen compounds. Part 56. Comparative syntheses and spectral properties of multiheterocyclic 2-<i>cis</i>-4-ansa and spiro-ferrocenyl (N/O)cyclotetraphosphazenes: Antituberculosis and antimicrobial activity and DNA interaction studies
  作者：Arzu Binici、Aytuğ Okumuş、Mehtap Yakut、Gamze Elmas、Zeynel Kılıç、Dila Koyunoğlu、Leyla Açık、Hülya Şimşek

  DOI：10.1080/10426507.2021.1986502

  日期：2022.1.2

  Abstract In the present study, two types of starting compounds; hexachloro(N/O)-cyclotetraphosphazenes containing mono-ferrocenyl-pendant arm, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa-(2,4-ansa; 2) and mono-ferrocenyl-spiro-(spiro; 3) were prepared by the reaction of N4P4Cl8 (1) with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide (L). Reactions of 2,4-ansa (2) with excess benzylamine and n-hexylamine

  摘要 在本研究中，两种类型的起始化合物；六氯(N/O)-环四磷腈含有单二茂铁基-侧臂，即单二茂铁基-2-顺-4-二氯-安萨-(2,4-安萨；2 )和单二茂铁-螺-(螺; 3 ) 由N 4 P 4 Cl 8 ( 1 ) 与3-( N-二茂铁甲基氨基)-1-丙氧化钠( L )反应制备。2,4-ansa ( 2 ) 与过量苄胺和正己胺的反应导致形成部分取代的 2 - cis -4-dichloro-ansa-cyclotetraphosphazenes ( 2a和2b )。相反，螺 ( 3 )用过量的苄胺和正己胺得到完全取代的单二茂铁-螺-环四磷腈 ( 3a和3b )。正如预期的那样，2,4-ansa 环四磷腈（2、2a和2b ）具有两个不同的立体 P 中心。通过元素分析、ESI-MS、FTIR、1 H、13 C 和31 P-NMR 技术评估环四磷腈的结构。对某些特定细菌和酵母菌株的抗菌和抗真菌
• Phosphorus–nitrogen compounds. Part 42. The comparative syntheses of 2-<i>cis</i>-4-ansa(N/O) and spiro(N/O) cyclotetraphosphazene derivatives: spectroscopic and crystallographic characterization, antituberculosis and cytotoxic activity studies
  作者：Arzu Binici、Aytuğ Okumuş、Gamze Elmas、Zeynel Kılıç、Nagehan Ramazanoğlu、Leyla Açık、Hülya Şimşek、Beste Çağdaş Tunalı、Mustafa Türk、Remziye Güzel、Tuncer Hökelek

  DOI：10.1039/c9nj00577c

  日期：——

  The reaction of N4P4Cl8 (1) with one equimolar amount of the sodium salt of an N/O donor-type bidentate ligand (2) afforded two kinds of derivatives, namely, mono-ferrocenyl-2-cis-4-dichloro-ansa- (2,4-ansa; 3) and mono-ferrocenyl-spiro- (spiro; 4) hexachlorocyclotetraphosphazenes. The reaction yield (35%) of 4 was significantly larger than that of 3 (14%). The 2,4-ansa compound (3) was reacted with

  N 4 P 4 Cl 8（1）与一摩尔当量的N / O供体型双齿配体（2）的钠盐反应，得到两种衍生物，即单二茂铁基-2-顺-4 -二氯-ansa-（2,4-ansa; 3）和单二茂铁基-spiro-（spiro; 4）六氯环四磷腈。的反应产率（35％）4比的显著更大3（14％）。使2,4-氨基苯甲酸酯化合物（3）与过量的仲胺反应，生成2-顺式-4-二氯-氨基苯甲酸酯-环四磷腈（3a–3d）。另一方面，螺环化合物（4）也可以用过量的单胺得到完全取代的单二茂铁基-螺环-环四磷腈（4a-4d）。通过ESI-MS和/或HRMS，FTIR，HSQC，HMBC，1 H，13 C和31 P NMR光谱和X射线晶体学（针对4）对四聚磷腈衍生物进行了表征。观察到2，4-氨基和螺环四磷腈具有不同的热稳定性。另外，新的单二茂铁基侧链的环四磷腈的CVs显示了Fe-redox中心的电化学可逆单电子氧化。2,4-an
• Phosphorus-nitrogen compounds. Part 52. The reactions of octachlorocyclotetraphosphazene with sodium 3-(N-ferrocenylmethylamino)-1-propanoxide: Investigations of spectroscopic, crystallographic and stereogenic properties
  作者：Gamze Elmas、Aytuğ Okumuş、Tuncer Hökelek、Zeynel Kılıç

  DOI：10.1016/j.ica.2019.119106

  日期：2019.11

  products were not observed by TLC and 31P NMR spectrum of the reaction mixture. The structures of cyclotetraphosphazene derivatives were verified by ESI-MS, FTIR, 1H, 13C and 31P NMR spectral data. The molecular and solid state structures of 3, 5 and 6 were established by X-ray diffraction method. The X-Ray crystallographic data indicate that compounds 3 and 6 have three-different and two equivalent chiral

  摘要八氯环四磷腈（四聚物，N4P4Cl8，1）与两摩尔当量的3-（N-二茂铁基甲基氨基）-1-丙醇钠（2）反应生成了新型ansa-spiro（3），2-trans-6-dispiro（ 4），2-顺-6-二螺（5），2-反-4-二螺（6）和2-顺-4-二螺（7）环四磷腈。然而，当用1和3摩尔当量的2进行反应时，相对于反应混合物的31P NMR谱观察到七个产物。这些产品中有五个被确定为3、4、5、6和7，其他两个产品预计是衍生自4和/或6和2的2-trans-4-trans-6-trispiro（8）。衍生自5和/或7的-trans-4-cis-6-trispiro（9）（未使用柱色谱法分离出两种trispiro产物（8和9））。此外，当反应以1和过量2进行时 通过反应混合物的TLC和31P NMR谱未观察到四螺产物。环四磷腈衍生物的结构通过ESI-MS，FTIR，1H，13C和31P NM
• Phosphorus–nitrogen compounds: Part 19. Syntheses, structural and electrochemical investigations, biological activities, and DNA interactions of new spirocyclic monoferrocenylcyclotriphosphazenes
  作者：Elif Ece İlter、Nuran Asmafiliz、Zeynel Kılıç、Leyla Açık、Makbule Yavuz、E. Burcu Bali、Ali Osman Solak、Fevziye Büyükkaya、Hakan Dal、Tuncer Hökelek

  DOI：10.1016/j.poly.2010.07.017

  日期：2010.10

  The reactions of hexachlorocyclotriphosphazatriene, N3P3Cl6, with N-alkyl-N-ferrocenylmethylethylene diamines, FcCH(2)NH(CH2)(2)NHR1 [R-1 = Me (1) and Et (2)], and sodium [3-(N-ferrocenylmethylamino)-1-propanoxide] (3) produce spirocyclic monoferrocenyl tetrachlorophosphazenes (1a-3a). The tetrapyrroli-dinophosphazenes (1b-3b) are prepared from the reactions of corresponding phosphazenes (1a-3a) with excess pyrrolidine. The reaction of 1a with excess morpholine affords geminal-morpholino phosphazene (1c), whilst the reactions of 2a and 3a give diethylaminotrimorpholino (2c) and fully substituted morpholino products (3c), respectively. The structural investigations of the compounds are examined by Fourier transform IR, MS, H-1, C-13, P-31 NMR, DEPT, HETCOR, and HMBC techniques. The crystal structures of 3b and 3c are determined using X-ray crystallography. Cyclic voltammetric and chronoamperometric data show that compounds 1a-3a, 1b-3b, and 1c-3c exhibit electrochemically reversible one-electron oxidation of Fc redox centers which are hardly affected by the substituents on the phosphazene ring. The compounds 1b, 2b, 3b, and 3c are screened for antibacterial activities against Gram-positive and Gram-negative bacteria and for antifungal activities against yeast strains. In addition, the antituberculosis activities (in vitro) of these compounds are evaluated against INH-susceptible reference strain M. tuberculosis H37Rv, and six multi-drug resistant clinical M. tuberculosis isolates. Compound 2b is found to be the most active against the susceptible the reference strain. In addition, 1b, 2b, and 3c are active against all the multidrug-resistant clinical isolates at the highest concentrations. Gel electrophoresis data indicate that the compounds promote the formation of strand breaks in plasmid DNA. Almost all the concentrations lost of supercoiled DNA suggests that the compound 3b is very efficient plasmid-modifier. The compounds inhibit BamHI cleavage of pUC18 DNA while restricting HindIII. (C) 2010 Elsevier Ltd. All rights reserved.