(S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine | 171196-82-0

• 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: (S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine
• 英文别名: (E,S)-N-(3-ethoxycarbonyl-2-propenyl)-N-(1-phenylethyl)amine；ethyl (S,E)-4-(N-α-methylbenzylamino)-2-butenoate；ethyl (E)-4-[[(1S)-1-phenylethyl]amino]but-2-enoate
• CAS: 171196-82-0
• 化学式: C₁₄H₁₉NO₂
• mdl: MFCD22966255
• 分子量: 233.31
• InChiKey: NEIKKEHCDJLCSG-PMDBQALLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.357
• 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：

  (S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine 在 盐酸 、 sodium hydroxide 、 disodium hydrogenphosphate 、 sodium amalgam 、 硼烷四氢呋喃络合物 、 sodium hydride 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.25h， 生成 methyl (3R,1'S)-<1-(1'-phenyleth-1'-yl)-pyrrolidin-3-yl> acetate
  参考文献：
  名称：

  Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid

  摘要：

  By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from H-1 NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.

  DOI：

  10.1016/0957-4166(95)00423-8
• 作为产物：
  描述：

  (S)-()-N-烯丙基-α-甲基苄胺 在 盐酸 、 正丁基锂 、 叔丁基锂 作用下， 反应 36.0h， 生成 (S)-N-<3-ethoxycarbonyl-2(E)-propen-1-yl>-N-(1-phenyleth-1-yl)amine
  参考文献：
  名称：

  Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis

  摘要：

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.

  DOI：

  10.1016/0957-4166(95)00271-p

文献信息

• Versatile Base-Catalyzed Route to Polycyclic Heteroaromatic Compounds by Intramolecular Aza-Michael Addition
  作者：Marco Bandini、Astrid Eichholzer、Magda Monari、Fabio Piccinelli、Achille Umani-Ronchi

  DOI：10.1002/ejoc.200601139

  日期：2007.6

  A catalytic new synthetic approach to 3,4-dihydropyrazino[1,2-a]indol-1(2H)-ones by intramolecular 1,4-addition of readily available α,β-unsaturated esters, is described. Here, the use of a range of organic as well as inorganic bases (5–10 mol-%) allowed a fast (30 min) and regioselective ring-closing reaction to be performed in high yields under simple operational conditions. Moreover, the protocol

  描述了一种通过分子内 1,4-加成容易获得的 α,β-不饱和酯来合成 3,4-二氢吡嗪并 [1,2-a]indol-1(2H)-ones 的一种新的催化合成方法。在这里，使用一系列有机和无机碱（5-10 mol%）可以在简单的操作条件下以高产率进行快速（30 分钟）和区域选择性的闭环反应。此外，该方案被有效地用作合成二溴吡咯并生物碱衍生物 N-Bn-longamide b 的关键步骤。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
• Thermodynamic vs. kinetic control in the stereoselective intramolecular conjugate addition of amide enolates leading to chiral trans-3,4-disubstituted pyrrolidin-2-ones
  作者：Roberta Galeazzi、Giovanna Mobbili、Mario Orena

  DOI：10.1016/s0040-4020(99)00091-5

  日期：1999.3

  Intramolecular conjugate addition of amide enolates to α,β-unsaturated esters was found to give either of the diastereomeric trans-3,4-disubstituted pyrrolidin-2-ones 6, 10 or 7, 11 as the major products, by choosing the appropriate reaction conditions. The cyclisation performed with NaH in THF afforded mainly 6 and 10, whereas by using sodium ethoxide in ethanol the major products of the cyclisation

  通过选择合适的反应，发现将酰胺烯酸酯分子内共轭加成到α，β-不饱和酯中可以得到非对映体反式-3,4-二取代吡咯烷-2-酮6、10或7、11的主要产物。情况。用NaH在THF中进行的环化反应主要得到6和10，而通过在乙醇中使用乙醇钠，环化的主要产物是异构体7和11，在C-3和C-4处的构型相反。这种行为通过热力学与动力学控制进行了解释，并得到了分子力学和量子力学计算的支持。
• Stereoselective reduction of chiral trans-3-acetyl-4-alkylpyrrolidin-2-ones
  作者：Roberta Galeazzi、Silvano Geremia、Giovanna Mobbili、Mario Orena

  DOI：10.1016/s0957-4166(99)00031-2

  日期：1999.2

  A number of trans-3-acetyl-4-alkylpyrrolidin-2-ones 8a-d and 11a,b were prepared and reduction of the keto group, carried out with KBH4 in CH3OH, led mainly to 3-hydroxyethylpyrrolidin-2-ones 13a-d and 19a,b with high stereoselection, Configuration of the newly formed stereogenic centre on the hydroxyethyl chain was assigned by H-1 NMR data supported by molecular mechanic calculations and eventually confirmed by X-ray diffraction analysis of p-iodobenzoate derivative 15. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Diastereomerically pure pyrrolidin-2-ones by intramolecular Michael reaction. Synthesis of both (S)- and (R)-3-pyrrolidineacetic acid
  作者：Roberta Galeazzi、Geremia Silvano、Mobbili Giovanna、Orena Mario

  DOI：10.1016/0957-4166(95)00423-8

  日期：1996.1

  By intramolecular conjugate addition of their derived enolates, the amides 5 and 6 gave diastereomeric mixtures of pyrrolidin-2-ones 10,11 and 12,13, in good yield and 80:20 d.r. After chromatographic separation, the configuration of pure diastereomers was assigned from H-1 NMR data. The usefulness of this intramolecular cyclisation was proven by conversion of either 10 or 12 into pyrrolidin-2-one 14 which through simple steps gave (S)-3-pyrrolidineacetic acid, 2. Following the same synthetic scheme, but starting from either 11 or 13, (R)-3-pyrrolidineacetic acid 3 was obtained.
• Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis
  作者：Miguel Yus、Francisco Foubelo、Larry R. Falvello

  DOI：10.1016/0957-4166(95)00271-p

  日期：1995.8

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.