N¹,N⁴-bis(o-nitrobenzenesulfonyl)-1,4-diaminobutane | 216504-01-7

• 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: N¹,N⁴-bis(o-nitrobenzenesulfonyl)-1,4-diaminobutane
• 英文别名: bis-N¹,N⁴-o-nitrophenylsulfonyl-1,4-diaminobutane；N,N'-bis(2-nitrobenzenesulfonyl)-1,4-butanediamine；N,N'-bis(2-nitrobenzenesulfonyl)butane-1,4-diamine；N,N'-bis(o-nitrobenzenesulfonyl)-1,4-diaminobutane；N,N'-butane-1,4-diylbis(2-nitrobenzenesulfonamide)；2-nitro-N-[4-[(2-nitrophenyl)sulfonylamino]butyl]benzenesulfonamide
• CAS: 216504-01-7
• 化学式: C₁₆H₁₈N₄O₈S₂
• mdl: MFCD00823312
• 分子量: 458.473
• InChiKey: SQCARJJMBMCNKD-UHFFFAOYSA-N

物化性质

• 熔点：
  185-186 °C
• 沸点：
  688.8±65.0 °C(Predicted)
• 密度：
  1.487±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  201
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  N¹,N⁴-bis(o-nitrobenzenesulfonyl)-1,4-diaminobutane 、 N-(benzyloxycarbonyl)-3-amino-1-bromobutane 在 potassium carbonate 、 苯硫酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以70%的产率得到N²,N¹³-bis(benzyloxycarbonyl)-2,13-diamino-5,10-diazatetradecane
  参考文献：
  名称：

  α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase

  摘要：

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.

  DOI：

  10.1021/jm050872h
• 作为产物：
  描述：

  邻硝基苯磺酰氯 、 四亚甲基二胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以91%的产率得到N¹,N⁴-bis(o-nitrobenzenesulfonyl)-1,4-diaminobutane
  参考文献：
  名称：

  New syntheses of α-methyl- and α,α′-dimethylspermine

  摘要：

  为了研究体外和体内多胺生物化学，我们从 N-（苄氧羰基）-3-氨基丁醇开始，高产合成了 α-甲基精胺和 α,α′-二甲基精胺。

  DOI：

  10.1007/s11171-005-0025-5

文献信息

• Aminooxy analogues of spermine and their monoacetyl derivatives
  作者：A. R. Simonyan、J. Vepsalainen、A. R. Khomutov

  DOI：10.1134/s1068162006060112

  日期：2006.12

  Convenient methods of synthesis of 1-aminooxy-3,8-diaza-11-aminoundecane, its earlier unknown N1-and N11-acetyl derivatives, and also 1,10-bis(aminooxy)-3,8-diazadecane are suggested. It is shown that it is possible to selectively delete the acid-labile ethoxyethylidene protection of aminooxy group by hydrosulfates in the presence of N-tert-butyloxycarbonyl group.

  建议了合成 1-氨基氧基-3,8-二氮杂-11-氨基十一烷、其早期未知的 N1-和 N11-乙酰衍生物以及 1,10-双(氨基氧基)-3,8-二氮杂癸烷的便捷方法。结果表明，在 N-叔丁氧基羰基存在下，可以通过硫酸氢盐选择性地消除氨氧基的酸不稳定乙氧基亚乙基保护。
• Rotaxanes of Cyclic Peptides
  作者：Vincent Aucagne、David A. Leigh、Julia S. Lock、Andrew R. Thomson

  DOI：10.1021/ja057206q

  日期：2006.2.1

  The synthesis of rotaxanes derived from the synthetic peptide macrocycles cyclo(l-ProGly)4 and cyclo(l-ProGly)5 and diammonium threads is described. [2]Rotaxanes are formed in good yields (56-63%), despite the disruption of internal amide-amide hydrogen bonding in the macrocycles.

  描述了衍生自合成肽大环环 (l-ProGly)4 和环 (l-ProGly)5 和二铵线的轮烷的合成。[2] 尽管大环中的内部酰胺-酰胺氢键被破坏，但仍以良好的产率 (56-63%) 形成轮烷。
• Nosyl (2-Nitrobenzenesulfonyl) Annulation Strategy toward Winding Vine-Shaped Bithiophenes
  作者：Shiomi Ashida、Naoki Tanaka、Yukiko Ito、Mitsuru Matsuoka、Takayoshi Hashimoto、Kentaro Okano、Yuji Miyazaki、Tohru Kobayashi、Tsuyoshi Yaita、Atsunori Mori

  DOI：10.1021/acs.joc.8b02382

  日期：2018.12.7

  Winding vine-shaped bithiophene was synthesized through the nosyl (2-nitrobenzenesulfonyl) cyclization protocol. The reaction of bithiophene bearing bromomethyl groups at the 3,3'-positions with nosylated 1,2-ethylenediamine in the presence of potassium carbonate afforded the annulated product in excellent yield. The obtained bithiophene was found to contain a 10-membered ring, which was confirmed by X-ray analysis. The related nosyldiamine bearing a tri- or tetramethylene group also reacted in a similar manner, affording an 11- or 12-membered macrocycle, respectively.
• α-Methyl Polyamines:  Efficient Synthesis and Tolerance Studies in Vivo and in Vitro. First Evidence for Dormant Stereospecificity of Polyamine Oxidase
  作者：Aki J. Järvinen、Marc Cerrada-Gimenez、Nikolay A. Grigorenko、Alex R. Khomutov、Jouko J. Vepsäläinen、Riitta M. Sinervirta、Tuomo A. Keinänen、Leena I. Alhonen、Juhani E. Jänne

  DOI：10.1021/jm050872h

  日期：2006.1.1

  Efficient syntheses of metabolically stable a-methylspermidine 1, alpha-methylspermine 2, and bis-alpha,alpha'methylated spermine 3 starting from ethyl 3-aminobutyrate are described. The biological tolerance for these compounds was tested in wild-type mice and transgenic mice carrying the metallothionein promoter-driven spermidine/spermine N-1-acetyltransferase gene (MT-SSAT). The efficient substitution of natural polyamines by their derivatives was confirmed in vivo with the rats harboring the same MT-SSAT transgene and in vitro with the immortalized fibroblasts derived from these animals. Enantiomers of previously unknown 1-amino-8-acetamido-5-azanonane dihydrochloride 4 were synthesized starting from enantiomerically pure (R)- and (S)-alaninols. The studies with recombinant human polyamine oxidase (PAO) showed that PAO (usually splits achiral substrates) strongly favors the (R)-isomer of 4 that demonstrates for the first time that the enzyme has hidden potency for stereospecificity.
• New syntheses of α-methyl- and α,α′-dimethylspermine
  作者：N. A. Grigorenko、J. Vepsalainen、A. Jarvinen、T. A. Keinanen、L. Alhonen、J. Janne、A. R. Khomutov

  DOI：10.1007/s11171-005-0025-5

  日期：2005.3

  α-Methylspermine and α,α′-dimethylspermine were synthesized in high overall yields starting from N-(benzyloxycarbonyl)-3-aminobutanol in order to study polyamine biochemistry in vitro and in vivo.

  为了研究体外和体内多胺生物化学，我们从 N-（苄氧羰基）-3-氨基丁醇开始，高产合成了 α-甲基精胺和 α,α′-二甲基精胺。