Methyl 4-[1-({[(tert-butoxy)carbonyl]amino}imino)ethyl]benzoate | 349111-15-5

• 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: Methyl 4-[1-({[(tert-butoxy)carbonyl]amino}imino)ethyl]benzoate
• 英文别名: methyl 4-[C-methyl-N-[(2-methylpropan-2-yl)oxycarbonylamino]carbonimidoyl]benzoate
• CAS: 349111-15-5
• 化学式: C₁₅H₂₀N₂O₄
• 分子量: 292.335
• InChiKey: DQYIKEHENIUSRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  77
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 4-[1-({[(tert-butoxy)carbonyl]amino}imino)ethyl]benzoate 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以76%的产率得到4-[1-(tert-butoxycarbonyl-hydrazino)-ethyl]-benzoic acid methyl ester
  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：

  肼基甲酸叔丁酯 、 4-乙酰基苯甲酸甲酯 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到Methyl 4-[1-({[(tert-butoxy)carbonyl]amino}imino)ethyl]benzoate
  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

• A C–H Activation-Based Strategy for <i>N</i>-Amino Azaheterocycle Synthesis
  作者：Pengfei Shi、Lili Wang、Shan Guo、Kehao Chen、Jie Wang、Jin Zhu

  DOI：10.1021/acs.orglett.7b02066

  日期：2017.8.18

  A C–H activation-based strategy has been developed for the synthesis of N-amino azaheterocycles. Rh(III)-catalyzed coupling of N-Boc hydrazones/N-Boc hydrazines with diazodiesters/diazoketoesters provides convenient access to synthetically and medicinally important compounds, N-amino isoquinolin-3-ones and N-amino indoles, by harnessing N-tert-butyloxycarbonyl (N-Boc) cleavage as an adaptable reactivity

  已经开发出基于AC–H活化的策略来合成N-氨基氮杂杂环。铑（III）催化的的耦合Ñ -Boc腙/ Ñ -Boc肼与diazodiesters / diazoketoesters提供了合成和医药上重要的化合物，方便地访问ñ -氨基异喹啉-3-酮和Ñ -氨基吲哚，通过利用Ñ -叔丁氧羰基（N -Boc）裂解作为一种适应性反应模式在不同的合成方案中。
• Synthesis of 2,3-Benzodiazepines via Rh(III)-Catalyzed C–H Functionalization of <i>N</i>-Boc Hydrazones with Diazoketoesters
  作者：Jie Wang、Lili Wang、Shan Guo、Shanke Zha、Jin Zhu

  DOI：10.1021/acs.orglett.7b01642

  日期：2017.7.7

  An efficient Rh(III)-catalyzed C–H activation protocol has been developed for the synthesis of 2,3-benzodiazepines with use of N-Boc hydrazones and diazoketoesters as substrates. The reaction features retention of the C═N and N–N bonds and selective cleavage of the N-Boc moiety.

  已经开发了一种有效的Rh（III）催化的C–H活化方案，以N- Boc azo和重氮酮酸酯为底物，用于合成2,3-苯并二氮杂s。该反应具有保留C═N和N–N键以及选择性切割N -Boc部分的特征。
• Pyridazinoquinolinetriones as NMDA Glycine-Site Antagonists with Oral Antinociceptive Activity in a Model of Neuropathic Pain
  作者：Thomas M. Bare、Dean G. Brown、Carey L. Horchler、Megan Murphy、Rebecca A. Urbanek、Vernon Alford、Christine Barlaam、Martin C. Dyroff、James B. Empfield、Janet M. Forst、Keith J. Herzog、Richard A. Keith、Alan S. Kirschner、Chi-Ming C. Lee、Joseph Lewis、Frances M. McLaren、Kathy L. Neilson、Gary B. Steelman、Shephali Trivedi、Edward P. Vacek、Wenhua Xiao

  DOI：10.1021/jm060212s

  日期：2007.6.1

  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.