N-acetyl-(R)-2-(4-hydroxyphenyl)glycine | 37784-23-9

• 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: N-acetyl-(R)-2-(4-hydroxyphenyl)glycine
• 英文别名: (2R)-2-acetamido-2-(4-hydroxyphenyl)acetic acid
• CAS: 37784-23-9
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: UVJQJJCJNQDKIY-SECBINFHSA-N

物化性质

• 沸点：
  514.9±45.0 °C(Predicted)
• 密度：
  1.349±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-(R)-2-(4-hydroxyphenyl)glycine 在 双氧水 、 horseradish peroxidase 作用下， 以91%的产率得到对羟基苯甲醛
  参考文献：
  名称：

  Enzymatic oxidative coupling of hydroxyphenylglycine derivatives

  摘要：

  In contrast to N-protected tyrosine derivatives, N-protected hydroxy-D-phenylglycine derivatives underwent decarboxylation to give 4-hydroxybenzaldehyde under the normal incubation conditions. When both the carboxyl and amino groups of hydroxy-D-phenylglycine are blocked, the C-C and C-O coupling products were obtained in 48% and 32% yields respectively. No racemization of the chiral center was observed for all the substrates examined. (C) 1998 Elsevier Science Ltd. AII rights reserved.

  DOI：

  10.1016/s0040-4039(98)01144-7
• 作为产物：
  描述：

  D(-)-对羟基苯甘氨酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.5h， 生成 N-acetyl-(R)-2-(4-hydroxyphenyl)glycine
  参考文献：
  名称：

  Agents de dédoublement. 3. Ethers benzyliques du (R)-(−) et du (S)-(+)-2-aminobutan-1-ol, et leur utilisation dans le dédoublement de dérivés N-acylés de la phénylglycine et de la p-hydroxyphénylglycine

  摘要：

  Treatment of the readily available (S)-(+) and (R)-(-) enantiomers of 2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding O-benzyl bases 4-7 ill good yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolutions of alpha-methylsuccinic acid (+/-)-9, N-acetylphenylglycine (+/-)-11, N-acetyl-(4-hydroxyphenyl) glycine (+/-)-14 and N-chloroacetyl-(4-hydroxyphenyl) glycine (+/-)-15.

  DOI：

  10.1016/0040-4020(94)01037-z

文献信息

• Racemization of Optically Active Aromatic<i>N</i>-Acetylamino Acids and Asymmetric Transformation of<i>N</i>-Acetyl-2-(4-hydroxyphenyl)glycine via Salt Formation with Optically Active α-Methylbenzylamine
  作者：Tadashi Shiraiwa、Shinji Sakata、Hisashi Natsuyama、Keiko Fujishima、Hideya Miyazaki、Satoru Kubo、Tomohisa Nitta、Hidemoto Kurokawa

  DOI：10.1246/bcsj.65.965

  日期：1992.4

  The racemization rates of N-acetyl-(S)-tyrosine, N-acetyl-(S)-phenylalanine, N-acetyl-(R)-2-(4-hydroxyphenyl)glycine [(R)-AcHpg], N-acetyl-(R)-2-phenylglycine, and N-acetyl-(S)-alanine were measured by use of (RS)-α-methylbenzylamine [(RS)-MBA] as a base-catalyst. The first-order rate constant for racemization tended to increase with an increase in the polar substituent constant of the N-acetylamino acid side chain. The racemization appeared to be subject to the inductive effect by the side chain. An asymmetric transformation of (RS)-AcHpg by using (R)-MBA, based on the result of racemization, gave an optically pure salt of (R)-AcHpg with (R)-MBA by successive use of the filtrate as the solvent. Optically pure (R)-2-(4-hydroxyphenyl)glycine [(R)-Hpg] was separated from the salt in 87–90% yield based on the starting (RS)-AcHpg. In addition, the asymmetric transformation of (R)-AcHpg was achieved by using (S)-MBA to give optically pure (S)-Hpg in 80% yield after purification of the salt of (S)-AcHpg with (S)-MBA followed by hydrolysis.

  以(RS)-α-甲基苄胺[(RS)-MBA]作为碱催化剂，测定了N-乙酰基-(S)-酪氨酸、N-乙酰基-(S)-苯丙氨酸、N-乙酰基-(R)-2-(4-羟基苯基)甘氨酸[(R)-AcHpg]、N-乙酰基-(R)-2-苯基甘氨酸和N-乙酰基-(S)-丙氨酸的消旋化速率。消旋化的速率常数（一级反应速率常数）通常随N-乙酰氨基酸侧链极性取代常数的增加而增加。消旋化过程似乎受侧链诱导效应的影响。基于消旋化结果，利用(R)-MBA对(RS)-AcHpg进行不对称转换，通过连续使用滤液作为溶剂，得到了光学纯的(R)-AcHpg与(R)-MBA的盐。从盐中分离光学纯的(R)-2-(4-羟基苯基)甘氨酸[(R)-Hpg]，基于起始的(RS)-AcHpg，产率为87-90%。此外，使用(S)-MBA实现了(R)-AcHpg的不对称转换，经(S)-AcHpg与(S)-MBA盐的纯化并随后水解，得到了产率为80%的光学纯(S)-Hpg。
• Inhibition of iodine-125 labeled ristocetin binding to Micrococcus luteus cells by the peptides related to bacterial cell wall mucopeptide precursors: quantitative structure-activity relationships
  作者：Ki-Hwan Kim、Yvonne Martin、Ellen Otis、James Mao

  DOI：10.1021/jm00121a018

  日期：1989.1

  Quantitative structure-activity relationships (QSAR) of N-Ac amino acids, N-Ac dipeptides, and N-Ac tripeptides in inhibition of 125I-labeled ristocetin binding to Micrococcus luteus cell wall have been developed to probe the details of the binding between ristocetin and N-acetylated peptides. The correlation equations indicate that (1) the binding is stronger for peptides in which the side chain of

  已开发了N-Ac氨基酸，N-Ac二肽和N-Ac三肽在抑制125I标记的瑞氏菌素与黄褐微球菌细胞壁结合中的定量构效关系（QSAR），以探索ristocetin之间的结合细节和N-乙酰化的肽 相关方程表明（1）对于C末端氨基酸侧链具有较大摩尔折射率（MR）值的肽，其结合作用更强；（2）对于极性肽，其结合作用较弱。 （3）N-Ac二肽中的N末端氨基酸对结合亲和力的贡献是C末端氨基酸的12倍，
• -Benzyl derivatives of (S)-(+) and (R)-(−)-2-aminobutan-1-ol as new resolving agents for racemic acids. Practical resolutions of -acyl derivatives of phenylglycine and 4-hydroxyphenylglycine
  作者：Joël Touet、Laurent Faveriel、Eric Brown

  DOI：10.1016/s0040-4039(00)60491-4

  日期：1993.4

  Treatment of the readily available (S)-(+) and (R)-(-)-2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding -benzyl bases 2-5 in high yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolution of -acetylphenylglycine (±)-7, -acety

  用氢化钠然后用苄基氯或取代的苄基卤处理易得的（S）-（+）和（R）-（-）-2-氨基丁-1-醇1，得到相应的-苄基碱2 -5高产。建议将这些新碱用于大规模拆分外消旋酸。例如，事实证明它们对于-乙酰基苯基甘氨酸（±）-7，-乙酰基- （4-羟苯基苯基）甘氨酸（±）-9和-氯乙酰基- （4-羟苯基）甘氨酸（±）-10的实际拆分有效。
• SHIRAIWA, TADASHI;SAKATA, SHINJI;FUJISHIMA, KAIKO;NATSUYAMA, HISASHI;KURO+, CHEM. EXPRESS, 5,(1990) N, C. 561-563
  作者：SHIRAIWA, TADASHI、SAKATA, SHINJI、FUJISHIMA, KAIKO、NATSUYAMA, HISASHI、KURO+

  DOI：——

  日期：——
• Agents de dédoublement. 3. Ethers benzyliques du (R)-(−) et du (S)-(+)-2-aminobutan-1-ol, et leur utilisation dans le dédoublement de dérivés N-acylés de la phénylglycine et de la p-hydroxyphénylglycine
  作者：Joël Touet、Laurent Faveriel、Eric Brown

  DOI：10.1016/0040-4020(94)01037-z

  日期：1995.2

  Treatment of the readily available (S)-(+) and (R)-(-) enantiomers of 2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding O-benzyl bases 4-7 ill good yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolutions of alpha-methylsuccinic acid (+/-)-9, N-acetylphenylglycine (+/-)-11, N-acetyl-(4-hydroxyphenyl) glycine (+/-)-14 and N-chloroacetyl-(4-hydroxyphenyl) glycine (+/-)-15.