ethyl 2-[(4-chlorobenzylidene)amino]butanoate | 126385-72-6

• 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: ethyl 2-[(4-chlorobenzylidene)amino]butanoate
• 英文别名: Ethyl 2-((4-chlorobenzylidene)amino)butanoate；ethyl 2-[(4-chlorophenyl)methylideneamino]butanoate
• CAS: 126385-72-6
• 化学式: C₁₃H₁₆ClNO₂
• 分子量: 253.729
• InChiKey: STDHSFDIEBEECQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 2-[(4-chlorobenzylidene)amino]butanoate 在 盐酸 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 0.33h， 生成 ethyl 2-amino-2-[(2-chloroethoxy)methyl]butanoate
  参考文献：
  名称：

  A facile synthesis of multigram quantity of ethyl 3-ethylmorpholine-3-carboxylate

  摘要：

  A five-step synthesis of ethyl 3-ethylmorpholine-3-carboxylate proceeding from readily available 2-aminobutyric acid is detailed herein. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.003
• 作为产物：
  描述：

  4-氯苯甲醛 、 2-氨基丁酸乙酯盐酸盐 在 magnesium sulfate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 以98%的产率得到ethyl 2-[(4-chlorobenzylidene)amino]butanoate
  参考文献：
  名称：

  A facile synthesis of multigram quantity of ethyl 3-ethylmorpholine-3-carboxylate

  摘要：

  A five-step synthesis of ethyl 3-ethylmorpholine-3-carboxylate proceeding from readily available 2-aminobutyric acid is detailed herein. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.03.003

文献信息

• Site-Selective γ-C(sp³)−H and γ-C(sp²)−H Arylation of Free Amino Esters Promoted by a Catalytic Transient Directing Group
  作者：Hua Lin、Chao Wang、Thomas D. Bannister、Theodore M. Kamenecka

  DOI：10.1002/chem.201802465

  日期：2018.7.5

  The first selective PdII‐catalysed γ‐C(sp3)−H and γ‐C(sp2)−H arylation of free amino esters using a commercially available catalytic transient directing group. A variety of free amino esters, including α‐amino esters and β‐amino esters, amino monoesters and amino bis‐esters, are shown to react with a diverse range of simple aryl and heteroaryl iodide reagents.

  首次使用选择性Pd II催化的游离氨基酯的γ-C（sp 3）-H和γ-C（sp 2）-H芳基化反应，使用市售的催化瞬态导向基团。各种游离的氨基酯，包括α-氨基酯和β-氨基酯，氨基单酯和氨基双酯，都可以与多种简单的碘化芳基和杂芳基试剂反应。
• Selective and Brain-Permeable Polo-like Kinase-2 (Plk-2) Inhibitors That Reduce α-Synuclein Phosphorylation in Rat Brain
  作者：Danielle L. Aubele、Roy K. Hom、Marc Adler、Robert A. Galemmo、Simeon Bowers、Anh P. Truong、Hu Pan、Paul Beroza、R. Jeffrey Neitz、Nanhua Yao、May Lin、George Tonn、Heather Zhang、Michael P. Bova、Zhao Ren、Danny Tam、Lany Ruslim、Jeanne Baker、Linnea Diep、Kent Fitzgerald、Jennifer Hoffman、Ruth Motter、Donald Fauss、Pearl Tanaka、Michael Dappen、Jacek Jagodzinski、Wayman Chan、Andrei W. Konradi、Lee Latimer、Yong L. Zhu、Hing L. Sham、John P. Anderson、Marcelle Bergeron、Dean R. Artis

  DOI：10.1002/cmdc.201300166

  日期：2013.8

  involved in the phosphorylation of α‐synuclein in Lewy bodies, which are one of the hallmarks of Parkinson’s disease neuropathology. Potent, selective, brain‐penetrant inhibitors of Plk‐2 were obtained from a structure‐guided drug discovery approach driven by the first reported Plk‐2–inhibitor complexes. The best of these compounds showed excellent isoform and kinome‐wide selectivity, with physicochemical

  Polo-like kinase-2（Plk-2）被认为是路易体中α-突触核蛋白磷酸化的主要激酶，这是帕金森氏病神经病理学的标志之一。有效的，选择性的，脑渗透性的Plk-2抑制剂是从第一个报道的Plk-2抑制剂复合物驱动的结构指导药物发现方法获得的。这些化合物中最好的化合物表现出出色的同工型和全基因组选择性，其理化特性足以证实体内Plk-2抑制作用。一种这样的化合物在口服后可显着降低大鼠脑内α-突触核蛋白的磷酸化，并为该治疗途径对帕金森氏病的潜在治疗的未来研究提供了有用的探针。
• Tracking a New Cell-Penetrating (W/R) Nonapeptide, through an Enzyme-Stable Mass Spectrometry Reporter Tag
  作者：Diane Delaroche、Baptiste Aussedat、Soline Aubry、Gérard Chassaing、Fabienne Burlina、Gilles Clodic、Gérard Bolbach、Solange Lavielle、Sandrine Sagan

  DOI：10.1021/ac061108l

  日期：2007.3.1

  We have designed a mass stable reporter (msr) tag with m/z over 500, trifluoroacetyl(α,α-diethyl)Gly-Lys(Nεbiotin)-(D)Lys-Cys, for the quantification of the uptake and study of the degradation processes of cell-penetrating peptides (CPP), by matrix assisted laser desorption/ionization time-of-flight (MALDI-TOF) mass spectrometry. This tag was found stable in cell lysis conditions. Using a quantitative MALDI-TOF mass spectrometry analysis based method, an accurate tracking of a new CPP and of its degradation products could be done. (1) The new msr(W/R) nonapeptide (H-RRWWRRWRR−NH2) enters chinese hamster ovary (CHO) K1 cells with a kinetic reaching a steady state after 30−60 min of incubation. This plateau was stable for 4 h and decreased slowly afterward. (2) The peptide msr(W/R) nonapeptide was not cytotoxic over 48 h incubation with CHO cells. (3) After 1 h incubation, the msr(W/R) nonapeptide accumulated with a 3-fold higher concentration than the extracellularly added concentration (7.5 μM). (4) The intracellular quantification was accurate with less than 3% of the quantified peptide being potentially membrane-bound. (5) There was no leakage of the full-length CPP outside the cells. And, finally, (6) analysis of the degradation process of this new CPP suggests that the peptide did not traffick to lyso-somes.

  我们设计了 m/z 超过 500 的质量稳定报告基因 (msr) 标签，三氟乙酰基 (α,α-二乙基)Gly-Lys(Nεbiotin)-(D)Lys-Cys，用于定量摄取和研究通过基质辅助激光解吸/电离飞行时间 (MALDI-TOF) 质谱分析细胞穿透肽 (CPP) 的降解过程。发现该标签在细胞裂解条件下稳定。使用基于定量 MALDI-TOF 质谱分析的方法，可以准确跟踪新的 CPP 及其降解产物。 (1) 新的 msr(W/R) 九肽 (H-RRWWRRWRR−NH2) 进入中国仓鼠卵巢 (CHO) K1 细胞，孵育 30−60 分钟后动力学达到稳定状态。该平台稳定了 4 小时，然后缓慢下降。 (2) 肽 msr(W/R) 九肽在与 CHO 细胞孵育 48 小时后没有细胞毒性。 (3)孵育1小时后，msr(W/R)九肽的累积浓度是细胞外添加浓度(7.5μM)的3倍。 (4) 细胞内定量准确，定量肽中潜在膜结合率低于 3%。 (5)全长CPP没有渗漏到细胞外。最后，(6) 对这种新 CPP 降解过程的分析表明，该肽没有运输到溶酶体。
• Phenylation of amino acid derivatives: A new route to α-phenyl-α-substituted amino acids
  作者：Martin J. O'Donnell、William D. Bennett、William N. Jacobsen、You-an Ma

  DOI：10.1016/s0040-4039(00)99282-7

  日期：1989.1
• A facile synthesis of multigram quantity of ethyl 3-ethylmorpholine-3-carboxylate
  作者：Jacek J. Jagodzinski、Danielle L. Aubele、David A. Quincy、Michael S. Dappen、Lee H. Latimer、Roy K. Hom、Robert A. Galemmo、Andrei W. Konradi、Hing L. Sham

  DOI：10.1016/j.tetlet.2011.03.003

  日期：2011.5

  A five-step synthesis of ethyl 3-ethylmorpholine-3-carboxylate proceeding from readily available 2-aminobutyric acid is detailed herein. (C) 2011 Elsevier Ltd. All rights reserved.