3-[(2-氨基乙基)硫代]-1-丙胺 | 56973-49-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: 3-[(2-氨基乙基)硫代]-1-丙胺
• 英文名称: 2-aminoethyl-3-aminopropylsulfide
• 英文别名: 1,6-Diamino-3-thiahexan；3-(2-aminoethylthio)propan-1-amine；Cystathionamine；3-(2-aminoethylsulfanyl)propan-1-amine
• CAS: 56973-49-0
• 化学式: C₅H₁₄N₂S
• 分子量: 134.246
• InChiKey: CFKGMBWSBBAQQO-UHFFFAOYSA-N

物化性质

• 沸点：
  248.1±25.0 °C(Predicted)
• 密度：
  1.013±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  8
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(2-氨基乙基)硫代]-1-丙胺 在 sodium hydroxide 、 氢溴酸 、 sodium hydride 、 苯酚 作用下， 以 乙醚 、 水 、 溶剂黄146 为溶剂， 反应 84.0h， 生成 1,4-diaza-7-thiacyclodecane
  参考文献：
  名称：

  Thermodynamic and Kinetic Studies of the Equilibration between the Sulfur- and Carbon-Bonded Forms of the Cobalt(III) Complex with the Ligands 1,4,7-Triazacyclononane and 1,4-Diaza-7-thiacyclodecane.

  摘要：

  The new cyclic thioether 1,4-diaza-7-thiacyclodecane, dathicd, has been synthesized and used for the preparation of the sulfur- and carbon-bonded cobalt(III) complexes: [Co(tacn)(S-dathicd)]Cl-3 . 5H(2)O and [Co(tacn)(C-dathicd)](ClO4)(2) (tacn, 1,4,7-triazacyclononane; C-dathicd, 1,4-diamino-7-thiacyclodecan-8-ide anion). A thermodynamic and kinetic study of the equilibration between these coordination compounds has been performed using W-VIS absorption spectroscopy, IE-HPLC and C-13 NMR ([OH-] = 10(-5)-1.0 M, T = 25.0 degrees C, I = 1.0 M). In basic solution Co(tacn)(S-dathicd)(3+) deprotonates at one of the coordinated amine groups and the base dissociation constant has been determined to K-b(NH) = 0.311 (32) M. The equilibrium constant for the reaction of Co(tacn)(S-dathicd)(3+) with hydroxide ions to give Co(tacn)(C-dathicd)(2+) has been determined to K-f = 1.8 x 10(5) M(-1) at 25 degrees C. The kinetic data have been interpreted in terms of the intermediate formation of a carbanion and this was strongly supported by C-13 NMR CH/CD-exchange studies. It was shown that Co(tacn)(S-dathicd)(3+) exchanges one methylene proton, and only one, prior to the formation of the alkyl complex. The subsequent reaction of the partially C-deuterated (-N-CH2-CH2-CHD-S-) cobalt-sulfur complex to form the alkyl complex gave 100% loss of deuterium. It is concluded that the labile methylene proton is bound to the carbon atom which in the alkyl complex is bound to cobalt(III). From the kinetic data it is estimated that the carbanion reacts with water 270 times faster than it is captured by cobalt(III).

  DOI：

  10.3891/acta.chem.scand.50-0853
• 作为产物：
  描述：

  半胱胺盐酸盐 、 丙烯胺 在 dipotassium peroxodisulfate 作用下， 以 水 为溶剂， 生成 3-[(2-氨基乙基)硫代]-1-丙胺
  参考文献：
  名称：

  Room temperature sonochemical initiation of thiol-ene reactions

  摘要：

  硫醇-烯烃“点击”反应已在多种原料烯烃中通过超声波在甲苯和水中进行。该方法在空气存在的水相中尤其有效。

  DOI：

  10.1039/c2cc32457a

文献信息

• Five-coordinate Copper(II) Complexes with a Thio Group as Type II Copper Models
  作者：Takeshi Sakurai、Shinnichiro Suzuki、Akitsugu Nakahara

  DOI：10.1246/bcsj.54.2313

  日期：1981.8

  Five-coordinate copper(II) complexes with a thio group were synthesized as non-blue copper(II) models by reactions of copper(II) perchlorate and condensation products of 2-pyridinecarbaldehyde or salicylaldehyde and bis(2-aminoethyl) sulfide or 2-aminoethyl 3-aminopropyl sulfide. In the complexes where thio group is coordinated to copper(II) at an equatorial position, the ESR spin Hamiltonian parameters

  通过高氯酸铜 (II) 与 2-吡啶甲醛或水杨醛与双 (2-氨基乙基) 硫化物或 2 -氨基乙基3-氨基丙基硫醚。在赤道位置硫基与铜(II)配位的配合物中，ESR自旋哈密顿参数g⁄⁄和A⁄⁄显着降低，并且由于硫到铜的电荷转移带出现在300-350nm处，偶尔出现在 400-500 纳米。另一方面，在轴向位置具有硫基的配合物在类似区域提供略小的 A⁄⁄ 值和强度较低的电荷转移带。已经讨论了向非蓝铜 (II) 捐献硫的生物学意义。
• Defining the Mechanism of Action and Enzymatic Selectivity of Psammaplin A against Its Epigenetic Targets
  作者：Matthias G. J. Baud、Thomas Leiser、Patricia Haus、Sharon Samlal、Ai Ching Wong、Robert J. Wood、Vanessa Petrucci、Mekala Gunaratnam、Siobhan M. Hughes、Lakjaya Buluwela、Fabrice Turlais、Stephen Neidle、Franz-Josef Meyer-Almes、Andrew J. P. White、Matthew J. Fuchter

  DOI：10.1021/jm2016182

  日期：2012.2.23

  Psammaplin A (11c) is a marine metabolite previously reported to be a potent inhibitor of two classes of epigenetic enzymes: histone deacetylases and DNA methyltransferases. The design and synthesis of a focused library based on the psammaplin A core has been carried out to probe the molecular features of this molecule responsible for its activity. By direct in vitro assay of the free thiol generated upon reduction of the dimeric psammaplin scaffold, we have unambiguously demonstrated that 11c functions as a natural prodrug, with the reduced form being highly potent against HDAC1 in vitro (IC50 0.9 nM). Furthermore, we have shown it to have high isoform selectivity, being 360-fold selective for HDAC1 over HDAC6 and more than 1000-fold less potent against HDAC7 and HDAC8. SAR around our focused library revealed a number of features, most notably the oxime functionality to be important to this selectivity. Many of the compounds show significant cytotoxicity in A549, MCF7, and W138 cells, with the SAR of cytotcodcity correlating to HDAC inhibition. Furthermore, compound treatment causes upregulation of histone acetylation but little effect on tubulin acetylation. Finally, we have found no evidence for 11c functioning as a DNMT inhibitor.
• Huys, C. T.; Goeminne, A. M., Zeitschrift fur Anorganische und Allgemeine Chemie
  作者：Huys, C. T.、Goeminne, A. M.

  DOI：——

  日期：——
• Biological analogs. Nature of the binding sites of copper-containing proteins
  作者：Alan R. Amundsen、John Whelan、B. Bosnich

  DOI：10.1021/ja00462a042

  日期：1977.9
• Kofod, Pauli; Larsen, Erik; Larsen, Sine, Acta Chemica Scandinavica, 1992, vol. 46, # 9, p. 841 - 853
  作者：Kofod, Pauli、Larsen, Erik、Larsen, Sine、Petersen, Carsten H.、Springborg, Johan、Wang, Dong-Ni

  DOI：——

  日期：——