苯丙氨酸,a-苯基-,甲基酯 | 118783-29-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 苯丙氨酸,a-苯基-,甲基酯
• 英文名称: methyl 2-amino-2,3-diphenylpropanoate
• 英文别名: 2-Amino-2,3-diphenyl-propionic acid methyl ester
• CAS: 118783-29-2
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: AEIUKLRACLSJGZ-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±37.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 苯丙氨酸,a-苯基-,甲基酯 在 palladium diacetate 、 对苯醌 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 methyl 1-oxo-3-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylate
  参考文献：
  名称：

  NH₂ As a Directing Group: From the Cyclopalladation of Amino Esters to the Preparation of Benzolactams by Palladium(II)-Catalyzed Carbonylation of N-Unprotected Arylethylamines

  摘要：

  An unusual NH2-directed Pd(II)-catalyzed carbonylation of quaternary aromatic alpha-amino esters to yield benzolactams has been developed. The steric hindrance around the amino group is pivotal for the success of the process. The stoichiometric cyclometalation of a variety amino esters has been studied in order to evaluate the influence of the different variables (size of the metallacycle, aromatic ring substituents, and steric bulk) in the process, and a complete kinetico-mechanistic study of the cyclopalladation process has been carried out. The experimental results indicate that the full substitution of the carbon in the alpha position of the amino esters plays an important role in their cyclopalladation reaction. The reaction shows a strong bias toward six-membered lactams over the five-membered analogues, which can be explained by a greater reactivity of the six-membered palladacycles.

  DOI：

  10.1021/om301140t
• 作为产物：
  描述：

  methyl 2-[(4-chlorophenyl)methylideneamino]-2,3-diphenylpropanoate 在 柠檬酸 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以1.1 g的产率得到苯丙氨酸,a-苯基-,甲基酯
  参考文献：
  名称：

  胺导向的钯催化苯丙氨酸衍生物的 C−H 卤化

  摘要：

  由于采用三氟乙酸作为添加剂的合适条件，在一系列季氨基酸 (AA) 衍生物上报道了苯丙氨酸衍生物的有效伯胺导向、钯催化的 C−H 卤化 (X=I, Br, Cl)。这种原始的天然官能团导向的邻位选择性卤化的扩展甚至用更具挑战性的天然苯丙氨酸作为叔 AA 得到了证明。

  DOI：

  10.1002/chem.202102411

文献信息

• Preparation of benzolactams by Pd(<scp>ii</scp>)-catalyzed carbonylation of N-unprotected arylethylamines
  作者：Blanca López、Aleix Rodriguez、David Santos、Joan Albert、Xavier Ariza、Jordi Garcia、Jaume Granell

  DOI：10.1039/c0cc03478a

  日期：——

  An unprecedented NH2-directed Pd(II)-catalytic carbonylation of quaternary aromatic α-amino esters to yield 6-membered benzolactams has been developed. The reaction shows a strong bias to 6-membered lactams over 5-membered ones. The steric hindrance around the amino group seems to be pivotal for the success of the process.

  研究人员开发了一种前所未有的 NH2 定向钯（II）催化季芳香族 α-氨基酯羰基化反应，生成 6 元苯内酰胺。与 5 元内酰胺相比，该反应更倾向于 6 元内酰胺。氨基周围的立体阻碍似乎是该过程成功的关键。
• Catalyst-free nitration of the aliphatic C H bonds of tertiary β-keto esters with tert-butyl nitrite: Access to α-quaternary α-amino acid precursors
  作者：Fu-Zhong Han、Lin-Lin Li、Li-Na Jia、Xiang-Ping Hu

  DOI：10.1016/j.tetlet.2022.153844

  日期：2022.6

  An efficient catalyst-free direct nitration of the CH bonds of tertiary β-keto esters using tert-butyl nitrite as a nitrating reagent is described. This radical nitration protocol tolerants diverse functional groups, leading to the preparation of linear and cyclic α-nitro-β-keto ester derivatives in good to excellent yields under mild conditions. In addition, the nitration product 3a was applied to

  描述了使用亚硝酸叔丁酯作为硝化试剂对叔 β-酮酯的 C H 键进行有效的无催化剂直接硝化。这种自由基硝化方案耐受不同的官能团，导致在温和条件下以良好至优异的产率制备线性和环状 α-硝基-β-酮酯衍生物。此外，将硝化产物3a应用于在锌粉和乙酸存在下的α-季铵α-氨基酸4的简明合成。
• Arylkalkyl-amines and -amides having anticonvulsant and neuroprotective properties
  申请人：Astra Aktiebolag

  公开号：EP0356035A2

  公开（公告）日：1990-02-28

  There is provided the use of a compound of formula I in the preparation of a medicament for use in the prevention or treatment of neurological disorders, wherein, Ar₁ and Ar₂, which may be the same or different, independently represent phenyl substituted by one or more of amino, nitro chlorine, bromine, hydroxy, C1 to 6 alkoxy, C1 to 6 alkyl or cyano; in addition one of Ar₁ or Ar₂ may also represent phenyl; R₁ represents hydrogen or C1 to 6 alkyl; R₂ represents hydrogen or COCH₂NH₂; R₃ represents hydrogen or C1 to 6 alkyl; provided that when R₂ represents hydrogen, then one or both of Ar₁ and Ar₂ may also represent phenyl, fluorophenyl or 2-, 3- or 4- pyridinyl and R₁ may also represent C1 to 6 alkoxycarbonyl or trifluoromethyl; or a pharmaceutically acceptable salt thereof. Some of the compounds of formula I are novel, and there are provided processes for making these, together with processes for making pharmaceutical compositions containing the novel compounds.

  提供了式 I 化合物在制备用于预防或治疗神经系统疾病的药物中的用途、 其中 Ar₁和Ar₂可以相同或不同，独立地代表被氨基、硝基氯、溴、羟基、C1～6 烷氧基、C1～6 烷基或氰基中的一个或多个取代的苯基；此外，Ar₁或Ar₂中的一个也可以代表苯基； R₁ 代表氢或 C1 至 6 烷基； R₂ 代表氢或 COCH₂NH₂； R₃ 代表氢或 C1 至 6 烷基； 但当 R₂ 代表氢时，Ar₁ 和 Ar₂ 中的一个或两个也可代表苯基、氟苯基或 2-、3- 或 4-吡啶基，R₁ 也可代表 C1-6 烷氧羰基或三氟甲基； 或其药学上可接受的盐。 式 I 的某些化合物是新型的，提供了制造这些化合物的工艺以及制造含有新型化合物的药物组合物的工艺。
• Arylalkylamides having neuroprotective properties
  申请人：FISONS CORPORATION

  公开号：EP0648489A1

  公开（公告）日：1995-04-19

  The use of 2-amino-N-(1,2-diphenyl-1-methylethyl)acetamide, 2-amino-N-(1,2-diphenylethyl)acetamide and 2-amino-N-[1,2-bis(4-fluorophenyl)-1-methylethyl]acetamide, and pharmaceutically acceptable salts thereof, as active ingredients in the manufacture of neuroprotective medicaments, is provided.

  提供了 2-氨基-N-(1,2-二苯基-1-甲基乙基)乙酰胺、2-氨基-N-(1,2-二苯基乙基)乙酰胺和 2-氨基-N-[1,2-双(4-氟苯基)-1-甲基乙基]乙酰胺及其药学上可接受的盐作为活性成分用于制造神经保护药物。
• Arylalkylamine having anticonvulsant and neuroprotective properties
  申请人：Astra Aktiebolag

  公开号：EP0648745A1

  公开（公告）日：1995-04-19

  The invention provides (S)-1-phenyl-2-(2-pyridinyl)ethylamine, and its pharmaceutically acceptable salts. The compound is indicated as an anticonvulsant and neuroprotective agent.

  本发明提供了(S)-1-苯基-2-(2-吡啶基)乙胺及其药学上可接受的盐类。该化合物可用作抗惊厥剂和神经保护剂。