(Z)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate | 625457-46-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (Z)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate
• 英文别名: ethyl (2Z)-4-((tert-butoxycarbonyl)amino)but-2-enoate；ethyl (Z)-4-[(2-methylpropan-2-yl)oxycarbonylamino]but-2-enoate
• CAS: 625457-46-7
• 化学式: C₁₁H₁₉NO₄
• 分子量: 229.276
• InChiKey: JVQHOURUZMGZAI-SREVYHEPSA-N

物化性质

• 熔点：
  48-50 °C
• 沸点：
  329.7±35.0 °C(predicted)
• 密度：
  1.044±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 (Z)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Michael Acceptor Based Antiplasmodial and Antitrypanosomal Cysteine Protease Inhibitors with Unusual Amino Acids

  摘要：

  New peptidic Michael acceptor based cysteine protease inhibitors displaying antiparasitic activity were identified by testing a broad series of 45 compounds in total, containing Asn, Gln, or Phe. As target enzymes, falcipain-2 and -3 from P. falciparum and rhodesain from T. b. rhodesiense were used. In the case of the Asn/Gln containing compounds, the trityl-protected, diastereomeric E-configured vinylogous dipeptide esters 16 (Boc-(S)-Phg-(R/S)-vGln(Trt)-OEt) were discovered as most active inhibitors concerning both protease inhibition and antiparasitic acitivity, with inhibition constants in the submicromolar range. The Compounds were shown to display time-dependent and competitive inhibition. In the case of the Phe containing Compounds, the maleic acid derivatives 42 and 43 (BnO-Phe <- Mal-Phe-OBn, BnO-Phe <- Mal-Phe-Ala-OBn. Mal = maleic acid) displayed good inhibition of rhodesain as well as good antitrypanosomal activity, while the fumaric acid derived E-analogue 14 (BnO-Phe <- Fum-Phe-OBn) only displayed inhibition or the target enzymes but no antiparasitic activity. Inhibition by these Phe derivatives was shown to be time-independent and competitive.

  DOI：

  10.1021/jm900946n
• 作为产物：
  描述：

  BOC-甘氨酸甲酯 在 lithium aluminium tetrahydride 、 草酰氯 、 potassium tert-butylate 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.83h， 生成 (Z)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate
  参考文献：
  名称：

  L-氨基酸合成手性 3,4-二取代吡咯

  摘要：

  描述了将天然氨基酸转化为 3,4-二取代吡咯的一般方法。适当保护的氨基酸(1)首先转化为相应的醛(2)。HornerEmmons 烯化为相应的 α,β-不饱和酯 (3) 提供了方便的入口。使用与甲苯磺酰甲基异氰化物 (TOSMIC) 的分子内环化反应一步完成吡咯环系统的构建。

  DOI：

  10.3987/com-02-9679

文献信息

• Iridium-Catalyzed Asymmetric Allylic Amination with Polar Amines: Access to Building Blocks with Lead-Like Molecular Properties
  作者：Paolo Tosatti、Joachim Horn、Amanda J. Campbell、David House、Adam Nelson、Stephen P. Marsden

  DOI：10.1002/adsc.201000721

  日期：2010.12.17

  dimethyl sulfoxide (DMSO) allowed, for the first time, the systematic exploitation of highly polar, functionalized amines in asymmetric allylic substitutions: low molecular weight, sp3-rich chiral building blocks were obtained with physicochemical properties that will be valuable in the synthesis of lead-like small molecules.

  空气稳定的铱催化剂和偶极非质子传递溶剂二甲基亚砜（DMSO）的组合首次允许在不对称的烯丙基取代中系统性地利用高极性，官能化的胺：低分子量，富含sp 3的手性体系获得具有理化性质的嵌段，这对于合成铅样小分子将是有价值的。
• The discovery and development of selective 3-fluoro-4-aryloxyallylamine inhibitors of the amine oxidase activity of semicarbazide-sensitive amine oxidase/vascular adhesion protein-1 (SSAO/VAP-1)
  作者：Jonathan S. Foot、Mandar Deodhar、Craig I. Turner、Ping Yin、Ellen M. van Dam、Diego G. Silva、Aldo Olivieri、Andrew Holt、Ian A. McDonald

  DOI：10.1016/j.bmcl.2012.04.111

  日期：2012.6

  A new class of 3-fluoroallyl amine-based SSAO/VAP-1 inhibitors is reported. These compounds have excellent selectivity over diamine oxidase, MAO-A and MAO-B. Synthesis and SAR studies leading to compound 28 (PXS-4159A) are reported. The pharmacokinetic profile of 28 in the rat, together with activity in a murine model of lung inflammation are also disclosed. (C) 2012 Elsevier Ltd. All rights reserved.
• Michael Acceptor Based Antiplasmodial and Antitrypanosomal Cysteine Protease Inhibitors with Unusual Amino Acids
  作者：Alexander Breuning、Björn Degel、Franziska Schulz、Christian Büchold、Martin Stempka、Uwe Machon、Saskia Heppner、Christoph Gelhaus、Matthias Leippe、Matthias Leyh、Caroline Kisker、Jennifer Rath、August Stich、Jiri Gut、Philip J. Rosenthal、Carsten Schmuck、Tanja Schirmeister

  DOI：10.1021/jm900946n

  日期：2010.3.11

  New peptidic Michael acceptor based cysteine protease inhibitors displaying antiparasitic activity were identified by testing a broad series of 45 compounds in total, containing Asn, Gln, or Phe. As target enzymes, falcipain-2 and -3 from P. falciparum and rhodesain from T. b. rhodesiense were used. In the case of the Asn/Gln containing compounds, the trityl-protected, diastereomeric E-configured vinylogous dipeptide esters 16 (Boc-(S)-Phg-(R/S)-vGln(Trt)-OEt) were discovered as most active inhibitors concerning both protease inhibition and antiparasitic acitivity, with inhibition constants in the submicromolar range. The Compounds were shown to display time-dependent and competitive inhibition. In the case of the Phe containing Compounds, the maleic acid derivatives 42 and 43 (BnO-Phe <- Mal-Phe-OBn, BnO-Phe <- Mal-Phe-Ala-OBn. Mal = maleic acid) displayed good inhibition of rhodesain as well as good antitrypanosomal activity, while the fumaric acid derived E-analogue 14 (BnO-Phe <- Fum-Phe-OBn) only displayed inhibition or the target enzymes but no antiparasitic activity. Inhibition by these Phe derivatives was shown to be time-independent and competitive.
• Synthesis of Chiral 3,4-Disubstituted Pyrroles from L-Amino Acids
  作者：Krishna L. Bhat、Jocelyn A. Hover、Charles W. Bock

  DOI：10.3987/com-02-9679

  日期：——

  A general methodology for the conversion of naturally occurring amino acids to 3,4-disubstituted pyrroles is described. A suitably protected amino acid (1) was first converted to the corresponding aldehyde (2). HornerEmmons olefination afforded a facile entry to the corresponding α,β-unsaturated ester (3). The construction of the pyrrole ring system was accomplished in a single step, using an intramolecular

  描述了将天然氨基酸转化为 3,4-二取代吡咯的一般方法。适当保护的氨基酸(1)首先转化为相应的醛(2)。HornerEmmons 烯化为相应的 α,β-不饱和酯 (3) 提供了方便的入口。使用与甲苯磺酰甲基异氰化物 (TOSMIC) 的分子内环化反应一步完成吡咯环系统的构建。