tert-butyl N-[4-(cyclohexylamino)-4-oxobutyl]carbamate | 144403-11-2

• 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 N-[4-(cyclohexylamino)-4-oxobutyl]carbamate
• CAS: 144403-11-2
• 化学式: C₁₅H₂₈N₂O₃
• 分子量: 284.399
• InChiKey: HCERYFVYTBCLRR-UHFFFAOYSA-N

物化性质

• 沸点：
  473.4±24.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[4-(cyclohexylamino)-4-oxobutyl]carbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 生成 H-γ-Abu-NH-cyclohexyl*HCl
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of novel clarithromycin derivatives with C-4″ elongated arylalkyl groups against macrolide-resistant strains

  摘要：

  Novel clarithromycin derivatives with C-4 '' elongated arylalkyl groups were designed, synthesized and evaluated to probe the effect of different lengths of their C-4 '' side chains on the activity against resistant bacterial strains. These derivatives had excellent activity against erythromycin-susceptible Streptococcus pneumoniae, Streptococcus aureus or Streptococcus pyogenes and some of them exhibited greatly improved activity against erythromycin-resistant strains. Compounds 18 and 16, which had the C-4 '' elongated arylalkyl groups with eight atoms from the 4 ''-oxygen atom to the terminal benzene ring, were the most effective against S. pneumoniae expressing the erm gene and the erm and me! genes. In contrast, the most potent compounds 3, 5, 9,17 and 18 against S. pneumoniae expressing the mef gene had C-4 '' elongated arylalkyl groups with three to eight atoms between the 4 ''-oxygen atom and the terminal aromatic ring. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.11.035
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 1-丙基磷酸酐 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 tert-butyl N-[4-(cyclohexylamino)-4-oxobutyl]carbamate
  参考文献：
  名称：

  Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory

  摘要：

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijms.2012.06.023

文献信息

• A new powerful method for the transformation of lactams into ω-amino-carboxamides under high pressure conditions
  作者：Hiyoshizo Kotsuki、Mitsuhiro Iwasaki、Hitoshi Nishizawa

  DOI：10.1016/s0040-4039(00)61241-8

  日期：1992.8

  High-pressure reaction of N-Boc-lactams with amines provides an efficient entry to ω-N-Boc-amino-carboxamide derivatives.

  的高压反应Ñ与胺-Boc内酰胺提供了一种有效条目ω- Ñ -Boc氨基羧酰胺衍生物。
• PROTEIN RECOGNIZING DRUG MOIETY OF ANTIBODY-DRUG CONJUGATE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP3831853A1

  公开（公告）日：2021-06-09

  A protein that recognizes a drug moiety of an antibody-drug conjugate in which a drug represented by the following formula is conjugated to an antibody via a linker, and a method for quantifying the concentration in plasma of an antibody-drug conjugate in a mammal to which the antibody-drug conjugate has been administered, by using the protein, and a method for identifying a tissue distribution of an antibody-drug conjugate.

  一种能识别抗体-药物共轭物中药物分子的蛋白质，在抗体-药物共轭物中，由下式表示的药物通过连接体与抗体共轭；一种利用该蛋白质定量检测注射了抗体-药物共轭物的哺乳动物血浆中抗体-药物共轭物浓度的方法；以及一种确定抗体-药物共轭物组织分布的方法。
• [EN] PROTEIN RECOGNIZING DRUG MOIETY OF ANTIBODY-DRUG CONJUGATE<br/>[FR] PROTÉINE RECONNAISSANT LA FRACTION MÉDICAMENTEUSE D'UN CONJUGUÉ ANTICORPS-MÉDICAMENT<br/>[JA] 抗体－薬物コンジュゲートの薬物部位を認識する蛋白質
  申请人：DAIICHI SANKYO CO LTD

  公开号：WO2020022475A1

  公开（公告）日：2020-01-30

  下式で示される薬物と、抗体とが、リンカーを介して結合した抗体－薬物コンジュゲートの、薬物部位を認識する蛋白質、及び該蛋白質を用いて、上記の抗体－薬物コンジュゲートを投与された哺乳動物における、該抗体－薬物コンジュゲートの血漿中濃度を定量する方法及び組織分布を確認する方法。
• Synthesis and antibacterial evaluation of novel clarithromycin derivatives with C-4″ elongated arylalkyl groups against macrolide-resistant strains
  作者：Shutao Ma、Bo Jiao、Yongjing Ju、Manjie Zheng、Ruixin Ma、Lin Liu、Ling Zhang、Xuecui Shen、Chenchen Ma、Ya Meng、Hui Wang、Yunkun Qi、Xiaodong Ma、Wenping Cui

  DOI：10.1016/j.ejmech.2010.11.035

  日期：2011.2

  Novel clarithromycin derivatives with C-4 '' elongated arylalkyl groups were designed, synthesized and evaluated to probe the effect of different lengths of their C-4 '' side chains on the activity against resistant bacterial strains. These derivatives had excellent activity against erythromycin-susceptible Streptococcus pneumoniae, Streptococcus aureus or Streptococcus pyogenes and some of them exhibited greatly improved activity against erythromycin-resistant strains. Compounds 18 and 16, which had the C-4 '' elongated arylalkyl groups with eight atoms from the 4 ''-oxygen atom to the terminal benzene ring, were the most effective against S. pneumoniae expressing the erm gene and the erm and me! genes. In contrast, the most potent compounds 3, 5, 9,17 and 18 against S. pneumoniae expressing the mef gene had C-4 '' elongated arylalkyl groups with three to eight atoms between the 4 ''-oxygen atom and the terminal aromatic ring. (C) 2010 Elsevier Masson SAS. All rights reserved.
• Fragmentation reactions of thiourea- and urea-compounds examined by tandem MS-, energy-resolved CID experiments, and theory
  作者：Francesco Falvo、Lukas Fiebig、Frank Dreiocker、Ran Wang、P.B. Armentrout、Mathias Schäfer

  DOI：10.1016/j.ijms.2012.06.023

  日期：2012.12

  Fragmentation reactions of thiourea- and urea-compounds, which are promising reagents for chemical crosslinking (XL), are investigated in detail by collision-induced dissociation (CID) experiments in a quadrupole ion trap (QIT), energy-resolved CID experiments, and computational modeling. For this study, an array of six labeled and unsymmetrical substituted thiourea- and urea-derivatives were synthesized, which allow unambiguous characterization of competing fragmentation pathways. The results of the QIT-CID-experiments are explored in detail for two compounds and confirmed by results for the other four. These results document the subtle competition of characteristic fragmentation pathways of this class of compounds. The multi dimensional investigations of the characteristic fragmentation reactions allow reliable structure proposals of prominent productions. Energy-dependent CID experiments on two of the six compounds lead to breakdown curves that show similar relative threshold energies for the formation of the product ions on which the functioning of the XL application relies. The experimental results are in full consistency with the results from in-depth computations. For the dominant fragmentations observed, the transition states for moving the proton from the most basic site of the precursor ion (the thiourea-sulfur or the urea carbonyl oxygen) to less basic heteroatoms in the protonated molecular ion is the necessary and decisive step that determines the extent of the charge-driven fragmentation processes that follow. (C) 2012 Elsevier B.V. All rights reserved.