2-phenyl-2-phthalimidopropionic acid | 24539-99-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-phenyl-2-phthalimidopropionic acid
• 英文别名: 2-phenyl-2-phthalimido-propionic acid；2-Phenyl-2-phthalimido-propionsaeure；(+/-)-N-Phthaloyl-α-methyl-phenylglycin；N-Phthaloyl-DL-α-methyl-phenylglycin；N-Phthaloyl-α-methyl-phenylglycin；(+/-)-N-Phthaloyl-α-methylglycin；2-(1,3-Dioxoisoindol-2-yl)-2-phenylpropanoic acid
• CAS: 24539-99-9；16707-50-9
• 化学式: C₁₇H₁₃NO₄
• 分子量: 295.295
• InChiKey: OSSSMIUWHFOPJW-UHFFFAOYSA-N

物化性质

• 熔点：
  122-124 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  486.1±38.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  74.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-2-phthalimidopropionic acid 在 三氯化铝 、 氯化亚砜 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 48.0h， 生成 1-methyl-1-phthalimido-2-tetralone
  参考文献：
  名称：

  Aminotetralone analogs of ketamine: synthesis and evaluation of hypnotic and locomotor properties in mice

  摘要：

  Ketamine and phencyclidine are structurally similar compounds that share many pharmacological actions, some of which are similar to the phenethylamines amphetamine and cathione. In order to integrate structural features of ketamine and cathinone, two groups of analogues, which are more conformationally restricted compared to the parent compounds, were synthesized for biological evaluation. These included 1-amino-1-methyl-2-tetralone and 2-amino-2-methyl-1-tetralone was well as several N-substituted derivatives of these molecules. Locomotor activity testing in mice revealed that 2-amino-2-methyl-1-tetralone caused an increase in locomotor activity while 1-amino-1-methyl-2-tetralone depressed spontaneous locomotor activity. None of the compounds produced hypnosis or profound ataxia.

  DOI：

  10.1021/jm00147a044
• 作为产物：
  描述：

  5-甲基-5-苯基乙内酰脲 在 barium dihydroxide 作用下， 180.0 ℃ 、392.24 kPa 条件下， 生成 2-phenyl-2-phthalimidopropionic acid
  参考文献：
  名称：

  A New Series of Anticonvulsant Drugs: Branched-Chain α-Aminoacetamides

  摘要：

  DOI：

  10.1021/jo01358a022

文献信息

• Studies on Optically Active Amino Acids. XIV. Studies on α-Alkyl-α-amino acids. VII. Determination of Absolute Configuration of Optically Active α-Methylphenylglycine Configuration of Optically Active α-Methylphenylglycine and 1-Methyl-1-phenylpropylamine.
  作者：Hatsuhiko Mizuno、Shiro Terashima、Kazuo Achiwa、Shunichi Yamada

  DOI：10.1248/cpb.15.1749

  日期：——

  The absolute configuration of (+)-α-methylphenylglycine was proved to be S series by the chemical correlation with R (-)-isovaline. Chemical scheme employed was shown in Chart 1. Moreover, in the course of the chemical correlation, the absolute configuration of (+)-1-methyl-1-phenylpropylamine was also proved to be R series. Preliminary experiments using racemic compounds were also described.

  通过与 R (-)-isovaline 的化学关联，证明 (+)-α-methylphenylglycine 的绝对构型为 S 系列。采用的化学方案如图 1 所示。此外，在化学关联过程中，(+)-1-甲基-1-苯基丙胺的绝对构型也被证明为 R 系列。此外，还介绍了使用外消旋化合物进行的初步实验。
• YANG, D. J.;DAVISSON, J. N., J. MED. CHEM., 1985, 28, N 9, 1361-1365
  作者：YANG, D. J.、DAVISSON, J. N.

  DOI：——

  日期：——