(S)-3-(4-Hydroxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester | 432515-18-9

• 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: (S)-3-(4-Hydroxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester
• 英文别名: tert-butyl (2S)-3-(4-hydroxyphenyl)-2-[(2,2,2-trifluoroacetyl)amino]propanoate
• CAS: 432515-18-9
• 化学式: C₁₅H₁₈F₃NO₄
• 分子量: 333.307
• InChiKey: BMIANAJXMVMPMR-NSHDSACASA-N

物化性质

• 沸点：
  429.5±45.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 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：
  75.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-3-(4-Hydroxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester 在 硝酸 、 溶剂黄146 作用下， 反应 1.0h， 以95%的产率得到(S)-3-(4-Hydroxy-3-nitro-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Chemoselective O -methylation of N -acylated/sulfonylated tyrosine derivatives

  摘要：

  Methyl ethers (6a and 6b) of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE. DIAD, MeOH). Williamson (Mel, K2CO3 or LiCO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives (7a and 7b) as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pK(a) values and steric factors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02349-8
• 作为产物：
  描述：

  L-酪氨酸叔丁酯 、 三氟乙酸酐 以 二氯甲烷 为溶剂， 反应 2.0h， 以95%的产率得到(S)-3-(4-Hydroxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-propionic acid tert-butyl ester
  参考文献：
  名称：

  Chemoselective O -methylation of N -acylated/sulfonylated tyrosine derivatives

  摘要：

  Methyl ethers (6a and 6b) of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE. DIAD, MeOH). Williamson (Mel, K2CO3 or LiCO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives (7a and 7b) as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pK(a) values and steric factors. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)02349-8

文献信息

• Chemoselective O -methylation of N -acylated/sulfonylated tyrosine derivatives
  作者：Mireille Attolini、Thierry Boxus、Stéphane Biltresse、Jacqueline Marchand-Brynaert

  DOI：10.1016/s0040-4039(01)02349-8

  日期：2002.2

  Methyl ethers (6a and 6b) of N-trifluoroacetyl- and N-(m-trifluoromethyl) phenylsulfonyl-6-nitro-tyrosine t-butyl ester were readily prepared by modified Mitsunobu reaction (DPPE. DIAD, MeOH). Williamson (Mel, K2CO3 or LiCO3 or NaOH under phase transfer) and classical Mitsunobu conditions (PPh3, DEAD, MeOH) gave O,N-dimethylated derivatives (7a and 7b) as side or main products. O- versus N-selectivity in tyrosine methylation reactions depends on both pK(a) values and steric factors. (C) 2002 Elsevier Science Ltd. All rights reserved.