l-Phenylalanine, N-pivaloyl-, methyl ester | 65638-80-4

• 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: l-Phenylalanine, N-pivaloyl-, methyl ester
• 英文别名: methyl 2-(2,2-dimethylpropanoylamino)-3-phenylpropanoate
• CAS: 65638-80-4
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: HKQYJNOOHJMWEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-benzyl-2-t-butyl-4-triphenylphosphonio-5(4H)-oxazolone bromide 在 氢碘酸 作用下， 以 二氯甲烷 为溶剂， 反应 70.0h， 以56%的产率得到l-Phenylalanine, N-pivaloyl-, methyl ester
  参考文献：
  名称：

  HYDRO-DE-PHOSPHONIATION OF 4-SUBSTITUTED-4-TRIPHENYLPHOSPHONIO-S(4H)-OXAZOLONES WITH HYDROGEN IODIDE

  摘要：

  4-Substituted-4-triphenylphosphonio-5(4H)-oxazolones, when reacted with hydrogen iodide in methylene chloride at room temperature, undergo hydro-de-phosphoniation to 5(4H)-oxazolonium salts, which react with methanol and triethylamine to give the corresponding N-acyl alpha-amino acid methyl esters. The possible mechanisms of hydro-de-phosphoniation is discussed.

  DOI：

  10.1080/10426509908037030

文献信息

• NOVEL CHIRAL DIHYDROBENZOAZAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF
  申请人：Boehringer Ingelheim International GmbH

  公开号：US20180155377A1

  公开（公告）日：2018-06-07

  This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands.

  这项发明涉及用于有机转化的新型磷配体。描述了在有机合成中制造和使用配体的方法。该发明还涉及用于制备新型配体的过程。
• Hydro-De-Phosphoniation of 4-Substituted-4-Triphenylphosphonio-5(4<i>H</i>)-Oxazolones With Alcohols
  作者：Roman Mazurkiewicz、Anna W Pierwocha、Anna Brachaczek、Iwona Mitrus

  DOI：10.1080/10426500008076324

  日期：2000.2

  Abstract 4-Substituted-4-triphenylphosphonro-5(4H)-oxazolones with a bulky alkyl substituent at the position 4 treated with MeOH in the presence of DBU (1.8-diazobicyclo[5.4.0]undec-7-ene) at room temperature give corresponding N-acyl-α-amino acid esters. In the case of a smaller substituent at the position 4 (Me, MeOCH2), the triphenylphosphonium group was competitively displaced by the methoxy group

  摘要 4-取代的-4-三苯基膦酰基-5(4H)-恶唑酮在室温下在 DBU（1.8-重氮双环[5.4.0]十一碳-7-烯）存在下用 MeOH 处理，在 4 位具有庞大的烷基取代基得到相应的 N-酰基-α-氨基酸酯。在 4 位取代基较小的情况下（Me，MeOCH2），三苯基鏻基团被甲氧基竞争性取代。在不存在 DBU 的情况下，在仅 150% 过量的 i-PrOH 存在下，在 CH2Cl2 中进行加氢脱膦可以避免后一反应。讨论了加氢脱膦酸化的可能机制。
• Cobalt‐Catalyzed Asymmetric Deuteration of α‐Amidoacrylates for Stereoselective Synthesis of α,β‐Dideuterated α‐Amino Acids
  作者：Aibo Li、Xinjian Song、Qiao Ren、Peiwang Bao、Xinyu Long、Fuli Huang、Lvjiang Yuan、Jianrong Steve Zhou、Xurong Qin

  DOI：10.1002/anie.202301091

  日期：——

  A cobalt-catalyzed enantioselective deuteration provides α,β-dideuterio-α-amino acids in excellent enantioselectivity and almost complete deuteration, using deuterated methanol as cheap deuterium source.

  使用氘化甲醇作为廉价的氘源，钴催化的对映选择性氘化以优异的对映选择性和几乎完全的氘化提供 α,β-二氘-α-氨基酸。
• Chiral dihydrobenzoazaphosphole ligands and synthesis thereof
  申请人：Boehringer Ingelheim International GmbH

  公开号：US10196413B2

  公开（公告）日：2019-02-05

  This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands.

  本发明涉及可用于有机转化的新型磷配体。本发明描述了在有机合成中制造和使用配体的方法。本发明还涉及制备新型配体的工艺。
• [EN] NOVEL CHIRAL DIHYDROBENZOAZAPHOSPHOLE LIGANDS AND SYNTHESIS THEREOF<br/>[FR] NOUVEAUX LIGANDS CHIRAUX DE DIHYDROBENZOAZAPHOSPHOLE ET LEUR SYNTHÈSE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2018106621A1

  公开（公告）日：2018-06-14

  This invention relates to novel phosphorous ligands useful for organic transformations. Methods of making and using the ligands in organic synthesis are described. The invention also relates to processes for preparing the novel ligands.