2-methyl-3-(4-nitrophenyl)propionic acid | 851968-99-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: 2-methyl-3-(4-nitrophenyl)propionic acid
• 英文别名: (R)-3-(4-nitrophenyl)-2-methylpropanoic acid；(R)-2-(4-nitrobenzyl)propanoic acid；(R)-2-methyl-3-(4-nitro-phenyl)-propionic acid；(R)-2-Methyl-3-(4-nitro-phenyl)-propionsaeure；(2R)-2-methyl-3-(4-nitrophenyl)propanoic acid
• CAS: 851968-99-5
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: SQSQBTYAUOXOJI-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(4-nitrophenyl)propionic acid 在 乙醇 、 铂 作用下， 生成 (R)-3-(4-amino-phenyl)-2-methyl-propionic acid
  参考文献：
  名称：

  Nerdel; John, Chemische Berichte, 1956, vol. 89, p. 1945,1949

  摘要：

  DOI：
• 作为产物：
  描述：

  2-methyl-3-(4-nitrophenyl)propanoic acid 在 1,7,7-三甲基双环[2.2.1]-2-庚胺 作用下， 生成 2-methyl-3-(4-nitrophenyl)propionic acid
  参考文献：
  名称：

  Nerdel; John, Chemische Berichte, 1956, vol. 89, p. 1945,1949

  摘要：

  DOI：

文献信息

• Enantioselective α-Benzylation of Aldehydes via Photoredox Organocatalysis
  作者：Hui-Wen Shih、Mark N. Vander Wal、Rebecca L. Grange、David W. C. MacMillan

  DOI：10.1021/ja106593m

  日期：2010.10.6

  The first enantioselective aldehyde α-benzylation using electron-deficient aryl and heteroaryl substrates has been accomplished. The productive merger of a chiral imidazolidinone organocatalyst and a commercially available iridium photoredox catalyst in the presence of household fluorescent light directly affords the desired homobenzylic stereogenicity in good to excellent yield and enantioselectivity

  第一个使用缺电子芳基和杂芳基底物的对映选择性醛α-苄基化已经完成。在家用荧光灯的存在下，手性咪唑烷酮有机催化剂和市售铱光氧化还原催化剂的生产性合并直接提供了所需的高苄基立体异构性，并具有良好到优异的产率和对映选择性。这种方法的效用已经通过快速获得对映体富集的药物靶点来抑制血管生成得到证明。
• Design and synthesis of a new polymer-supported Evans-type oxazolidinone: an efficient chiral auxiliary in the solid-phase asymmetric alkylation reactions
  作者：Tomoya Kotake、Yoshio Hayashi、S. Rajesh、Yoshie Mukai、Yuka Takiguchi、Tooru Kimura、Yoshiaki Kiso

  DOI：10.1016/j.tet.2005.01.135

  日期：2005.4

  ee) and moderate to good overall yield (up to 70%, for 3 steps), which were comparable to those of the conventional solution-phase methods. Furthermore, recovery and recycling of the polymer-supported chiral auxiliary were successfully achieved without decreasing the stereoselectivity of the product. Therefore, this is the first successful example that the solid-phase Evans' asymmetric enolate-alkylation

  Wang树脂支撑的Evans手性助剂（23）是基于一种新颖的聚合物固定策略设计的，该策略利用了恶唑烷酮环的5位，并开发了适用于一天之内多克制备的新合成路线。23衍生的N上的固相Evans不对称烷基化-酰酰亚胺树脂和随后的氢过氧化物锂介导的化学选择性水解，可提供所需的高立体选择性（最高97％ee）和中等至良好的总收率（3步最高可达70％）的相应α-支链羧酸。与传统的固溶相方法相比。此外，在不降低产物的立体选择性的情况下，成功地实现了聚合物负载的手性助剂的回收和再循环。因此，这是在固体载体上有效地进行固相埃文斯不对称烯醇烷基化的第一个成功实例，并且得出的结论是，通过恶唑烷酮环的5-位与固体载体的连接是固相埃文斯手性助剂的理想策略。
• Highly Rigid Diphosphane Ligands with a Large Dihedral Angle Based on a Chiral Spirobifluorene Backbone
  作者：Xu Cheng、Qi Zhang、Jian‐Hua Xie、Li‐Xin Wang、Qi‐Lin Zhou

  DOI：10.1002/anie.200462072

  日期：2005.2.4
• Chiral linker 5: scope and limitations of arylsubstituted m-hydrobenzoins as solid supported open chain chiral auxiliaries for diastereoselective syntheses
  作者：Joachim Broeker、Max Knollmueller、Peter Gaertner

  DOI：10.1016/j.tetasy.2009.02.004

  日期：2009.2

  The applicability of five aryl substituted m-hydrobenzoin ethers already tested in the L-Selectride (R) mediated stereoselective reduction of phenylglyoxylates as open chain chiral auxiliaries was further investigated via the alpha-alkylation of propionates, the addition of n-BuZnCl to phenylglyoxylates and the Diels-Alder reaction of acrylates with cyclopentadiene as model reactions. As up to 90% cle could be achieved in the solution phase, two optimized auxiliary structures were immobilized on commercially available Wang-resin and applied as a reusable solid supported chiral auxiliaries in the same type of reactions. (C) 2009 Elsevier Ltd. All rights reserved.