1,5-bis(methylsulfonyloxy)-3-aza-3-(p-toluenesulfonylamido)pentane | 52601-81-7

• 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: 1,5-bis(methylsulfonyloxy)-3-aza-3-(p-toluenesulfonylamido)pentane
• 英文别名: 4-methyl-N,N-bis(2-methylsulfonyloxyethyl)benzenesulfonamide；2-[(4-methylphenyl)sulfonyl-(2-methylsulfonyloxyethyl)amino]ethyl methanesulfonate
• CAS: 52601-81-7
• 化学式: C₁₃H₂₁NO₈S₃
• 分子量: 415.51
• InChiKey: KDRHRBJZVCMOOL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,5-bis(methylsulfonyloxy)-3-aza-3-(p-toluenesulfonylamido)pentane 在 disodium hydrogenphosphate 、 sodium amalgam 、 sodium 、 汞 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 48.0h， 以95%的产率得到5,6,14,15-二苯并-4,7,13,16-四氧杂-1,10-二氮杂环十八碳-5,14-二烯
  参考文献：
  名称：

  Chromogenic and Fluorogenic Crown Ether Compounds for the Selective Extraction and Determination of Hg(II)

  摘要：

  Two novel crown ether compounds, N,N'-bis(2-hydroxy-5-nitrobenzyl)-4,13-diazadibenzo-18-crown-6 (CCE) and N,N'-bis(7-hydroxy-4-methylcoumarin-8-methylene)-4,13-diazadibenzo-18-crown-6 (FCE), have been synthesized as potential reagents for the selective extraction and determination of heavy metal ions, Characterizations of the acid-base reactivity and the heavy metal ion extraction capabilities are reported, Both CCE and FCE undergo four-step ionization processes with associated tautomeric transformations and form stable complexes with divalent metal cations that can be extracted into 1,2-dichloroethane, Extraction constants for Ba(II), Ca(II), Cd(II), Cu(II), Hg(II), Pb(II), and Sr(II) have been determined for both reagents, For CCE, the extraction order is Hg(II) much greater than Pb(II) > Cu(II) > Cd(II) > Ca(II) > Sr(II) > Ba(II), whereas the order for FCE is Hg(II) much greater than Cu(II) > Pb(II) > Cd(II) > Ca(II) > Sr(II) > Ba(II), The selectivity of CCE for Hg(II) over the next-best-extracted cation, Pb(II), is similar to 2 x 10(7) and that of FCE for Hg(II) over next-best-extracted cation, Cu(II), is similar to 5 x 10(6), Potential applications to chemical analysis, based on the unprecedented selectivity of both reagents for Hg(II), are briefly examined.

  DOI：

  10.1021/ac00118a012
• 作为产物：
  描述：

  N,N-双-(2-羟乙基)-对甲苯磺酰胺 、 甲基磺酰氯 在 吡啶 作用下， 生成 1,5-bis(methylsulfonyloxy)-3-aza-3-(p-toluenesulfonylamido)pentane
  参考文献：
  名称：

  抗肿瘤剂：X. N-双（2-氟乙基）胺

  摘要：

  发现将 N-双(2-羟乙基)-对甲苯磺酰胺 (Ib) 连续转化为相应的二甲磺酸盐和二氟衍生物 (IIa、IIIa 和 IIIc) 为制备 N-双 (2-氟乙基) 胺提供了便利的途径。N-双(2-甲磺酰基-氧乙基)-对甲苯磺酰胺 (IIIa) 与有限量的氟化钾在几种质子溶剂中的反应显示生成 N-(对甲苯磺酰基) 吗啉 (IV)。通过合成两种 N-双（2-氟乙基）苄胺（IXb 和 Xa）来说明 N-双（2-氟乙基）胺作为氟氮芥的前体的用途。还建议使用氯化铝-氢化铝锂试剂进行碳-氟键的氢解。

  DOI：

  10.1139/v64-084

文献信息

• New Synthetic Routes for 1-Benzyl-1,4,7,10-tetraazacyclododecane and 1,4,7,10-Tetraazacyclododecane-1-acetic Acid Ethyl Ester, Important Starting Materials for Metal-coded DOTA-Based Affinity Tags
  作者：Stephan W. Kohl、Katharina Kuse、Markus Hummert、Herbert Schumann、Clemens Mügge、Katharina Janek、Hardy Weißhoff

  DOI：10.1515/znb-2007-0313

  日期：2007.3.1

  Two improved routes to synthesize 1-benzyl-1,4,7,10-tetraazacyclododecane (6) and 1,4,7,10- tetraazacyclododecane-1-acetic acid ethyl ester (11) are described as well as the synthesis of 1-2-[4-(maleimido-N-propylacetamidobutyl)amino]-2-oxoethyl}-1,4,7,10-tetraazacyclododecane- 4,7,10-triacetic acid (17) and its Y, Ho, Tm, and Lu complexes. The 1H and 13C NMR spectra of the new compounds as well as

  描述了合成 1-苄基-1,4,7,10-四氮杂环十二烷 (6) 和 1,4,7,10- 四氮杂环十二烷-1-乙酸乙酯 (11) 的两种改进路线以及 1 -2-[4-(马来酰亚胺-N-丙基乙酰胺丁基)氨基]-2-氧乙基}-1,4,7,10-四氮杂环十二烷-4,7,10-三乙酸(17)及其Y、Ho、Tm , 和 Lu 络合物。新化合物的 1H 和 13C NMR 谱以及中间体 4-苄基-1,7-双(对甲苯磺酰基)二亚乙基三胺 (3) 和 1,4,7-tris 的单晶 X 射线结构分析(对甲苯磺酰基)二亚乙基三胺(7)进行了报道和讨论。17 的稀土配合物已通过 1 H NMR 光谱和 MALDI-TOF 质谱进行表征。
• Synthesis, Structure−Activity Relationships, and Biological Properties of 1-Heteroaryl-4-[ω-(1<i>H</i>-indol-3-yl)alkyl]piperazines, Novel Potential Antipsychotics Combining Potent Dopamine D₂ Receptor Antagonism with Potent Serotonin Reuptake Inhibition
  作者：Pieter Smid、Hein K. A. C. Coolen、Hiskias G. Keizer、Rolf van Hes、Jan-Peter de Moes、Arnold P. den Hartog、Bob Stork、Rob H. Plekkenpol、Leonarda C. Niemann、Cees N. J. Stroomer、Martin Th. M. Tulp、Herman H. van Stuivenberg、Andrew C. McCreary、Mayke B. Hesselink、Arnoud H. J. Herremans、Chris G. Kruse

  DOI：10.1021/jm050148z

  日期：2005.11.1

  A series of novel bicyclic 1-heteroaryl-4-[omega-(1H-indol-3-yl)alkyl]piperazines was synthesized and evaluated on binding to dopamine D(2) receptors and serotonin reuptake sites. This class of compounds proved to be potent in vitro dopamine D(2) receptor antagonists and in addition were highly active as serotonin reuptake inhibitors. Some key representatives showed potent pharmacological in vivo activities

  合成了一系列新颖的双环1-杂芳基-4- [ω-（1H-吲哚-3-基）烷基]哌嗪，并评估了与多巴胺D（2）受体和5-羟色胺再摄取位点的结合。这类化合物被证明是有效的体外多巴胺D（2）受体拮抗剂，此外还具有作为5-羟色胺再摄取抑制剂的高活性。一些主要代表在口服阿扑吗啡诱导的爬升的拮抗作用和5-HTP诱导的小鼠行为的拮抗作用中均显示出口服给药后体内的有效药理活性。根据临床前数据，8- 4- [3-（5-氟-1H-吲哚-3-基）丙基]哌嗪-1-基} -4H-苯并[1,4]恶嗪-（R选择）-2-甲基-3-酮（45c，SLV314）进行临床开发。体外和体内研究表明45c具有良好的药代动力学特性和较高的CNS血浆比例。
• Dual NK1 antagonists—serotonin reuptake inhibitors as potential antidepressants. Part 2: SAR and activity of benzyloxyphenethyl piperazine derivatives
  作者：Thomas Ryckmans、Olivier Berton、Renée Grimée、Thierry Kogej、Yves Lamberty、Patrick Pasau、Patrice Talaga、Christophe Genicot

  DOI：10.1016/s0960-894x(02)00563-2

  日期：2002.11

  piperazine derivatives combining NK(1) antagonism and serotonin reuptake inhibition is described. Compound 7u was shown to be active in animal models of 5-HT reuptake inhibition and central NK(1) receptor blockade, and was demonstrated to be orally active in an integrated model sensitive to both mechanisms. This class of compounds potentially represents a new generation of antidepressants.

  描述了结合NK（1）拮抗作用和5-羟色胺再摄取抑制作用的苄氧基苯乙基哌嗪衍生物的合成，结构亲和关系和活性。化合物7u在抑制5-HT再摄取和中枢NK（1）受体的动物模型中显示出活性，并在对两种机制均敏感的综合模型中显示出口服活性。这类化合物可能代表了新一代的抗抑郁药。
• ANTINEOPLASTIC AGENTS: X. N-BIS(2-FLUOROETHYL)AMINES
  作者：George R. Pettit、Robert L. Smith

  DOI：10.1139/v64-084

  日期：1964.3.1

  Successive conversion of N-bis(2-hydroxyethyl)-p-toluenesulphonamide (Ib) to respective dimethanesulphonate and difluoro derivatives (IIa, IIIa, and IIIc) was found to provide a convenient route to N-bis(2-fluoroethyl)amine. Reaction of N-bis(2-methanesulphonyl-oxyethyl)-p-toluenesulphonamide (IIIa) with limited quantities of potassium fluoride, in several pro tic solvents, was shown to yield N-(p

  发现将 N-双(2-羟乙基)-对甲苯磺酰胺 (Ib) 连续转化为相应的二甲磺酸盐和二氟衍生物 (IIa、IIIa 和 IIIc) 为制备 N-双 (2-氟乙基) 胺提供了便利的途径。N-双(2-甲磺酰基-氧乙基)-对甲苯磺酰胺 (IIIa) 与有限量的氟化钾在几种质子溶剂中的反应显示生成 N-(对甲苯磺酰基) 吗啉 (IV)。通过合成两种 N-双（2-氟乙基）苄胺（IXb 和 Xa）来说明 N-双（2-氟乙基）胺作为氟氮芥的前体的用途。还建议使用氯化铝-氢化铝锂试剂进行碳-氟键的氢解。
• Sodium Amalgam: A Highly Efficient Reagent for the Detosylation of Azathiacrown Ethers
  作者：John W. Sibert、Philip B. Forshee

  DOI：10.1055/s-2006-926338

  日期：——

  A simple, nearly quantitative method is demonstrated for the deprotection of tosylated mixed azathiacrown ethers using sodium amalgam. Four macrocycles, containing differing numbers of amino groups and ring sizes, were prepared using traditional cyclization procedures and the described deprotection technique. Three of the macrocycles, [12]aneNS3, [14]aneNS3, and [15]aneN2S3, were reported previously, though either in low yields, only in protected form, or using hazardous precursors, while the fourth, [18]aneN3S3, is a new ionophore.

  本研究展示了一种使用汞齐钠对甲苯磺酰化混合氮杂冠醚进行脱保护的简单、近乎定量的方法。利用传统的环化程序和所述的脱保护技术制备了含有不同数量氨基和环尺寸的四个大环。其中三个大环，即 [12]aneNS3、[14]aneNS3 和 [15]aneN2S3 以前已有报道，但要么产率低，要么只是受保护的形式，要么使用了危险的前体。