(R)-tert-butyl 2-(methylamino)-3-phenylpropanoate | 114525-95-0

• 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: (R)-tert-butyl 2-(methylamino)-3-phenylpropanoate
• 英文别名: N-Methyl-D-phenylalanine tert-butyl ester；tert-butyl (2R)-2-(methylamino)-3-phenylpropanoate
• CAS: 114525-95-0
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: UZKARLOPBFXQHH-GFCCVEGCSA-N

物化性质

• 沸点：
  323.3±30.0 °C(Predicted)
• 密度：
  1.005±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险性防范说明：
  P264,P280,P302+P352,P337+P313,P305+P351+P338,P362+P364,P332+P313
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  (R)-tert-butyl 2-(methylamino)-3-phenylpropanoate 在 palladium on activated charcoal 盐酸 、 氢气 、 2-bromo-1-ethylpyridin-1-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 29.0h， 生成 [(2S)-3-methyl-1-[methyl-[(2R)-1-[(2-methylpropan-2-yl)oxy]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxobutan-2-yl] (2S)-2-[[(3S)-3-hydroxy-2,2-dimethyloct-7-ynoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  The Total Synthesis and Stereochemical Revision of Yanucamide A

  摘要：

  GraphicsThe first total synthesis of yanucamide A is reported via amide and ester couplings of the key components. This synthesis has established the configuration at the previously ambiguous 3-position, and also revised the stereochemistry at the 22-position, to give 3S, 12S, 17S, 22S for the natural product.

  DOI：

  10.1021/ol034803d
• 作为产物：
  描述：

  N-苄氧羰基-D-苯丙氨酸 在 4-二甲氨基吡啶 、 10% palladium hydroxide on charcoal 、 D(+)-10-樟脑磺酸 、 氢气 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 37.5h， 生成 (R)-tert-butyl 2-(methylamino)-3-phenylpropanoate
  参考文献：
  名称：

  Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists

  摘要：

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.

  DOI：

  10.1021/ml400528y

文献信息

• Modulators of hERAP2 discovered by high-throughput screening
  作者：Laura Medve、Ronan Gealageas、Bao Vy Lam、Valentin Guillaume、Omar Castillo-Aguilera、Virgyl Camberlein、Catherine Piveteau、Melissa Rosell、Charlotte Fleau、Sandrine Warenghem、Julie Charton、Julie Dumont-Ryckembusch、Damien Bosc、Florence Leroux、Peter van Endert、Benoit Deprez、Rebecca Deprez-Poulain

  DOI：10.1016/j.ejmech.2020.113053

  日期：2021.2
• Design, Synthesis, and Optimization of Balanced Dual NK₁/NK₃Receptor Antagonists
  作者：Stephen Hanessian、Thomas Jennequin、Nicolas Boyer、Vincent Babonneau、Udaykumar Soma、Clotilde Mannoury la Cour、Mark J. Millan、Guillaume De Nanteuil

  DOI：10.1021/ml400528y

  日期：2014.5.8

  In connection with a program directed at potent and balanced dual NK1/NK3 receptor ligands, a focused exploration of an original class of peptidomimetic derivatives was performed. The rational design and molecular hybridization of a novel phenylalanine core series was achieved to maximize the in vitro affinity and antagonism at both human NK1 and NK3 receptors. This study led to the identification of a new potent dual NK1/NK3 antagonist with pK(i) values of 8.6 and 8.1, respectively.
• The Total Synthesis and Stereochemical Revision of Yanucamide A
  作者：Zhengshuang Xu、Yungui Peng、Tao Ye

  DOI：10.1021/ol034803d

  日期：2003.8.1

  GraphicsThe first total synthesis of yanucamide A is reported via amide and ester couplings of the key components. This synthesis has established the configuration at the previously ambiguous 3-position, and also revised the stereochemistry at the 22-position, to give 3S, 12S, 17S, 22S for the natural product.