N,N'-Dibenzyl-N,N'-dimethylsulfoxylsaeure-diamid | 53370-29-9

• 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: N,N'-Dibenzyl-N,N'-dimethylsulfoxylsaeure-diamid
• 英文别名: Bis(N-benzyl-N-methylamino)-sulfid；Bis-(N-benzyl-N-methylamino)-sulfid；Bis(benzylmethylamino)sulfide；N-[benzyl(methyl)amino]sulfanyl-N-methyl-1-phenylmethanamine
• CAS: 53370-29-9
• 化学式: C₁₆H₂₀N₂S
• 分子量: 272.414
• InChiKey: WNEFWIOLJTXZQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±48.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  31.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-Dibenzyl-N,N'-dimethylsulfoxylsaeure-diamid 在 二氯化硫 作用下， 以 乙醚 为溶剂， 生成 N-benzyl-N-methylaminosulfenyl chloride
  参考文献：
  名称：

  Neidlein, Richard; Lenhard, Thomas, Chemische Berichte, 1983, vol. 116, # 9, p. 3133 - 3140

  摘要：

  DOI：
• 作为产物：
  描述：

  bis(dimethylamino)sulfide 、 N-甲基苄胺 以 苯 为溶剂， 反应 24.0h， 生成 N-(dimethylaminosulfanyl)-N-methyl-1-phenylmethanamine 、 N,N'-Dibenzyl-N,N'-dimethylsulfoxylsaeure-diamid 、 二甲胺
  参考文献：
  名称：

  Synthesis of the First Poly(diaminosulfide)s and an Investigation of Their Applications as Drug Delivery Vehicles

  摘要：

  This paper reports the first examples of poly(diaminosulfide)s that were synthesized by the reaction of a sulfur transfer reagent and several secondary diamines. The diaminosulfide group has the general structure of R2N-S-NR2, and although it has been used in the synthesis of small molecules, it has never been utilized in the synthesis of macromolecules until this report. A series of poly(diaminosulfide)s were synthesized at elevated temperatures, and the molecular weights of the polymers were as high as 12 400 g mol(-1) with conversions for the polymerization reaction up to 99%. The rate constants for the transamination reactions that lead to the polymers were measured in several solvents to provide an understanding of the reaction conditions necessary to polymerize the monomers. The degradation of diaminosulfides was studied in D2O, C6D6, CD3OD, CDCl3, and DMSO-d(6)/D2O to demonstrate that they were very stable in organic solvents but degraded within hours under aqueous conditions. These results clearly demonstrated that diaminosulfides are very stable in organic solvents under ambient conditions. Poly(diaminosulfide)s have sufficient stabilities to be useful for many applications. The ability of these polymers to function as drug delivery vehicles was studied by the fabrication of nanoparticles of a water-insoluble poly(diaminosulfide) with a dye. The microparticles were readily absorbed into human embryonic 293 cells and possessed no measurable toxicity toward these same cells.

  DOI：

  10.1021/ma2023167

文献信息

• Neuartige Schwefelylide
  作者：Klaus Hartke、Elisabeth Kohrt

  DOI：10.1002/ardp.19933260503

  日期：——

  AbstractDie Kondensation der Succinimido‐sulfonium‐chloride 4 mit den Malonsäurederivaten 5 unter Triethylamin‐Katalyse liefert die Schwefelylide 6. In analoger Weise erhält man mit den Alkyliden‐malondinitrilen 7 die Schwefelylide 8, mit den Alkyliden‐cyanessigestern 9 die Schwefelylide 10, mit den Cycloalkyliden‐malonsäurederivaten 11 die Schwefelylide 12 und mit den N‐Cyaniminen 13 die Schwefelylide 14. Die gelösten Ylide 8, 10 und 14 liegen in der Regel als cis/trans‐Isomerengemische vor.
• NEIDLEIN, R.;LENHARD, T., CHEM. BER., 1983, 116, N 9, 3133-3140
  作者：NEIDLEIN, R.、LENHARD, T.

  DOI：——

  日期：——
• Neidlein, Richard; Lenhard, Thomas, Chemische Berichte, 1983, vol. 116, # 9, p. 3133 - 3140
  作者：Neidlein, Richard、Lenhard, Thomas

  DOI：——

  日期：——
• Synthesis of the First Poly(diaminosulfide)s and an Investigation of Their Applications as Drug Delivery Vehicles
  作者：Jun Yoo、Sheetal R. D’Mello、Tyler Graf、Aliasger K. Salem、Ned B. Bowden

  DOI：10.1021/ma2023167

  日期：2012.1.24

  This paper reports the first examples of poly(diaminosulfide)s that were synthesized by the reaction of a sulfur transfer reagent and several secondary diamines. The diaminosulfide group has the general structure of R2N-S-NR2, and although it has been used in the synthesis of small molecules, it has never been utilized in the synthesis of macromolecules until this report. A series of poly(diaminosulfide)s were synthesized at elevated temperatures, and the molecular weights of the polymers were as high as 12 400 g mol(-1) with conversions for the polymerization reaction up to 99%. The rate constants for the transamination reactions that lead to the polymers were measured in several solvents to provide an understanding of the reaction conditions necessary to polymerize the monomers. The degradation of diaminosulfides was studied in D2O, C6D6, CD3OD, CDCl3, and DMSO-d(6)/D2O to demonstrate that they were very stable in organic solvents but degraded within hours under aqueous conditions. These results clearly demonstrated that diaminosulfides are very stable in organic solvents under ambient conditions. Poly(diaminosulfide)s have sufficient stabilities to be useful for many applications. The ability of these polymers to function as drug delivery vehicles was studied by the fabrication of nanoparticles of a water-insoluble poly(diaminosulfide) with a dye. The microparticles were readily absorbed into human embryonic 293 cells and possessed no measurable toxicity toward these same cells.