tert-butyl 2-(thiophen-3-ylmethyl)hydrazinecarboxylate | 1026335-48-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl 2-(thiophen-3-ylmethyl)hydrazinecarboxylate
• 英文别名: tert-butyl N-(thiophen-3-ylmethylamino)carbamate
• CAS: 1026335-48-7
• 化学式: C₁₀H₁₆N₂O₂S
• 分子量: 228.315
• InChiKey: GXQVEQNKJFOSRN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-(thiophen-3-ylmethyl)hydrazinecarboxylate 在 甲烷磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 7-chloro-4-hydroxy-2-(thien-3-ylmethyl)-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s
• 作为产物：
  描述：

  tert-butyl N-(thiophen-3-ylmethylideneamino)carbamate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 tert-butyl 2-(thiophen-3-ylmethyl)hydrazinecarboxylate
  参考文献：
  名称：

  Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain

  摘要：

  A series of 7-chloro-2,3-dihydro-2-[1-(pyridinyl)alkyl]-pyridazino[4,5-b]quinoline-1,4,10(5H)-triones were synthesized and found to have potent activity at the glycine site of the NMDA receptor. In some cases, these compounds possessed poor aqueous solubility that may have contributed to poor rat oral bioavailability. Subsequently, compounds have been identified with improved aqueous solubility and oral bioavailability. Several of these compounds were examined in a rat chronic constrictive injury (CCI) model of neuropathic pain and found to have potent activity when dosed orally.

  DOI：

  10.1021/jm060212s

文献信息

• N-Boc-O-Tosyl Hydroxylamine as a Safe and Efficient Nitrogen Source for the N-Amination of Aryl and Alkyl Amines: Electrophylic Amination
  作者：Sivalingam Thambidurai、Thankappan Baburaj

  DOI：10.1055/s-0030-1261170

  日期：2011.9

  In our published paper, we have reported the formation of hydrazine derivatives by electrophilic amination using N-Boc-Otosylhydroxylamine. From the available literature (J. Vidal et al. Chem. Eur. J. 1997, 3, 1691; J. G. Krause et al. Tetrahedron Lett. 2010, 51, 3568; W. Hartmann Synthesis 1988, 807; A. Armstrong et al. Org Lett. 2005, 7, 713), we conclude that the structures assigned are erroneous

  在我们发表的论文中，我们报道了使用 N-Boc-Otosyl 羟胺通过亲电胺化形成肼衍生物。来自现有文献（J. Vidal 等人 Chem. Eur. J. 1997, 3, 1691; JG Krause 等人 Tetrahedron Lett. 2010, 51, 3568; W. Hartmann Synthesis 1988, 807; A. Armstrong 等人. Org Lett. 2005, 7, 713)，我们得出结论，指定的结构是错误的，实际产物是异构脲衍生物，由 Lossen 重排形成，如下所示。