ethyl β-anylinobutyrate | 30448-31-8

• 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 β-anylinobutyrate
• 英文别名: ethyl 3-(phenylamino)butanoate；Ethyl 3-anilinobutanoate；Ethyl 3-anilinobutyrate；3-anilino-butyric acid ethyl ester；3-Anilino-buttersaeure-aethylester；β-Anilino-buttersaeure-aethylester
• CAS: 30448-31-8
• 化学式: C₁₂H₁₇NO₂
• 分子量: 207.272
• InChiKey: YBISWBSFVLJVLN-UHFFFAOYSA-N

物化性质

• 沸点：
  154-156 °C(Press: 13 Torr)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl β-anylinobutyrate 在 4-二甲氨基吡啶 、 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 3.0h， 生成 N-(hex-4-yn-2-yl)-N-phenylpivalamide
  参考文献：
  名称：

  Stereodefined Homopropargyl Amines by Tandem Nucleophilic Addition/Fragmentation of Dihydropyridone Triflates

  摘要：

  Dihydropyridone (DHPD) triflates undergo nucleophile-triggered fragmentation to provide homopropargyl amine derivatives, the stereochemistry of which is defined by starting from readily available beta-amino esters.

  DOI：

  10.1021/ol102760q
• 作为产物：
  描述：

  3-(苯基氨基)-2-丁烯酸乙酯 在 bis(1,5-cyclooctadiene)iridium(I) tetrakis[3,5-bis(trifluoromethyl)phenyl]borate 、 氢气 、 三乙胺 、 (S_a)-2-(piperidin-1-yl)-dinaphtho[2,1-d:1',2'-f][1,3,2] dioxaphosphepine 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、2.5 MPa 条件下， 反应 16.0h， 生成 ethyl β-anylinobutyrate
  参考文献：
  名称：

  Synthesis of N-phenyl β-amino acids via iridium-catalyzed asymmetric hydrogenation using mixed monodentate ligands

  摘要：

  The iridium-catalyzed asymmetric hydrogenation of N-phenyl-beta-dehydroamino acid derivatives was examined using monodentate phosphoramidite ligands. The highest yields and enantioselectivities were obtained using a mixed ligand approach with PipPhos L1 and achiral triphenylphosphine (full conversion, 70% ee). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.11.026

文献信息

• Hydrogenation of β-N-Substituted and β-N,N-Disubstituted Enamino Esters in the Presence of Iridium(I) Catalyst
  作者：Christian Bruneau、Jean-Luc Renaud、Hania Hebbache、Zakia Hank

  DOI：10.1055/s-0029-1217405

  日期：2009.8

  Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50 ˚C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields.

  在温和的条件下，通过两个简单步骤，从δ-酮酯衍生物和伯胺、仲胺制备出了几种新的δ-氨基酯。在铱催化剂的作用下，各种烯氨基酯在 50 ˚C 下进行氢化反应。高产率地分离出了新的δ-N-取代氨基酯。
• Tetrahydroquinoline derivatives as CRTH2 antagonists
  作者：Jiwen Liu、Yingcai Wang、Ying Sun、Derek Marshall、Shichang Miao、George Tonn、Penny Anders、Joel Tocker、H. Lucy Tang、Julio Medina

  DOI：10.1016/j.bmcl.2009.10.094

  日期：2009.12

  A series of tetrahydroquinoline-derived inhibitors of the CRTH2 receptor was discovered by a high throughput screen. Optimization of these compounds for potency and pharmacokinetic properties led to the discovery of potent and orally bioavailable CRTH2 antagonists. (C) 2009 Elsevier Ltd. All rights reserved.
• N,2-Dilithioalkylamines from Aziridines by Naphthalene-Catalyzed Reductive Opening. Synthetic Applications
  作者：Juan Almena、Francisco Foubelo、Miguel Yus

  DOI：10.1021/jo00090a044

  日期：1994.6

  The reductive opening of aziridines 1a-c with lithium in the presence of a catalytic amount of naphthalene at -78 degrees C led to the corresponding dianionic intermediates 2a-c, which are stable species under these reaction conditions and react with electrophilic reagents [H2O, D2O, Me(2)S(2), Bu(t)CHO, PhCHO, Me(2)CO, (CH2)(5)CO, (EtO)(2)CO, CH2=CHCO(2)Me, PhCON(CH2)(4), PhCH=NPh, MeI, and CH2=CHCH2Br] to give, after hydrolysis with water, the corresponding difunctionalized compounds 3-5. When the reductive opening and the reaction with electrophiles [H2O, D2O, CH2=CHCH2Br, Me(2)CO, (c-C3H5)(2)CO] were carried out on chiral aziridines 8 and 9, enantiomerically pure difunctionalized compounds 12 were obtained with same stereochemistry, independently of the stereochemistry of diastereomeric starting aziridines 8 and 9.
• Efficient Rhodium-Catalyzed Asymmetric Hydrogenation for the Synthesis of a New Class of <i>N</i>-Aryl β-Amino Acid Derivatives
  作者：Qian Dai、Weiran Yang、Xumu Zhang

  DOI：10.1021/ol0523897

  日期：2005.11.1

  N-Aryl beta-amino esters were obtained by asymmetric hydrogenation of a new class of N-aryl beta-enamino esters. High conversions and up to 96.3% ee values were achieved with a Rh-TangPhos catalyst.
• Chemo- and Diastereoselective Reduction of .beta.-Enamino Esters: A Convenient Synthesis of Both cis- and trans-.gamma.-Amino Alcohols and .beta.-Amino Esters
  作者：Giuseppe Bartoli、Cristina Cimarelli、Enrico Marcantoni、Gianni Palmieri、Marino Petrini

  DOI：10.1021/jo00097a039

  日期：1994.9

  Convenient procedures for the chemo- and diastereoselective reduction of beta-enamino esters 1 are described. Both cis- and trans-gamma-amino alcohols 2 or beta-amino esters 3 can be prepared by reduction of beta-enamino esters 1, readily available starting materials, with the use of inexpensive reagents Nali-PrOH or NaHbB(OAc)(3)/AcOH, respectively, and the appropriate reduction conditions. The mechanisms and diastereoselectivities for the reductions are discussed. The relative configurations and conformations of the diastereoisomeric gamma-amino alcohols 2 and beta-amino esters 3 obtained are established by H-1 and C-13 NMR study and unequivocally set by their cyclic derivatives tetrahydro-1,3-oxazines 4.