l-Valine, N-(p-anisoyl)-, methyl ester | 251538-67-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: l-Valine, N-(p-anisoyl)-, methyl ester
• 英文别名: methyl 2-[(4-methoxybenzoyl)amino]-3-methylbutanoate
• CAS: 251538-67-7
• 化学式: C₁₄H₁₉NO₄
• mdl: MFCD03447569
• 分子量: 265.309
• InChiKey: WRAADPRVDXVRFM-UHFFFAOYSA-N

物化性质

• 熔点：
  88-90 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  415.6±30.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)
• 保留指数：
  2054

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 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：

  l-Valine, N-(p-anisoyl)-, methyl ester 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 4-isopropyl-2-(4-methoxyphenyl)oxazol-5(4H)-one
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524
• 作为产物：
  描述：

  D,L-valine 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 l-Valine, N-(p-anisoyl)-, methyl ester
  参考文献：
  名称：

  Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

  摘要：

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.

  DOI：

  10.1021/jacs.5b10524

文献信息

• A chiral cobalt(<scp>ii</scp>) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines
  作者：Baiwei Ma、Weiwei Luo、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c7cc01278k

  日期：——

  A highly efficient catalytic asymmetric Formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N'-dioxide/Co(BF4)2.6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained...

  通过手性N，N'-二氧化物/Co(BF4)2.6H2O络合物实现了5-烷氧基恶唑与偶氮二羧酸酯化合物的高效催化不对称形式[3 + 2]环加成反应。获得了一系列多取代的1,2,4-三唑啉化合物。
• Probing the Efficiency of N-Heterocyclic Carbene Promoted <i>O</i>- to C-Carboxyl Transfer of Oxazolyl Carbonates
  作者：Jennifer E. Thomson、Craig D. Campbell、Carmen Concellón、Nicolas Duguet、Kathryn Rix、Alexandra M. Z. Slawin、Andrew D. Smith

  DOI：10.1021/jo702720a

  日期：2008.4.1

  Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at < 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.
• The effect of substituents on the chiral solvating properties of (S)-1,6-dialkylpiperazine-2,5-diones
  作者：Črt Malavašič、Branko Stanovnik、Jernej Wagger、Jurij Svete

  DOI：10.1016/j.tetasy.2011.07.019

  日期：2011.6

  The effect of substituents on the chiral solvating properties of 13 different (S)-1,6-dialkylpiperazine-2,5-diones (S)-1a-m and five (35,6S)-1,3,6-trialkyl analogues (S,S)-1n-r was studied by NMR in CDCl(3) with methyl (RS)-N-benzoylleucinate (RS)-2a as the model analyte. Most diketopiperazines exhibited typical resolution, Delta Delta delta(-20)(RS) similar to 0.1 ppm. Increased performance was observed with 6-CH(2)R substituted compounds (S)-1h-j. The best resolution of the NH protons of (R)-2a and (S)-2a, Delta Delta delta(-2)(RS)0 = 0.227 ppm, was obtained with (S)-1-isopropyl-6-(4-nitrobenzyl)piperazine-2,5-dione (S)-1j. An additional syn-oriented substituent at the C(3) position decreased the enantioselectivity. Association constants for the binding of (S)-1j to each enantiomer of (RS)-2a in CDCl(3) at -20 degrees C were determined by NMR titration. (C) 2011 Elsevier Ltd. All rights reserved.
• Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and <i>N</i>,<i>O</i>-Acetal Derivatives
  作者：Tianli Wang、Zhaoyuan Yu、Ding Long Hoon、Claire Yan Phee、Yu Lan、Yixin Lu

  DOI：10.1021/jacs.5b10524

  日期：2016.1.13

  Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective gamma-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective gamma-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronudeophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective gamma-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched alpha,alpha-disubstituted alpha-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and gamma-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nudeophilic oxazolide and the electrophilic phosphonium intermediate.