rac-N-benzyl-N-methylserine methyl ester | 403804-62-6

• 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: rac-N-benzyl-N-methylserine methyl ester
• 英文别名: methyl 2-(benzyl(methyl)amino)-3-hydroxypropanoate；N-Methyl-N-(phenylmethyl)serine methyl ester；methyl 2-[benzyl(methyl)amino]-3-hydroxypropanoate
• CAS: 403804-62-6
• 化学式: C₁₂H₁₇NO₃
• 分子量: 223.272
• InChiKey: IAEYTLAMYSGRJG-UHFFFAOYSA-N

物化性质

• 沸点：
  346.8±32.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  rac-N-benzyl-N-methylserine methyl ester 在 盐酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 2-(Benzyl-methyl-amino)-3-mercapto-propionic acid
  参考文献：
  名称：

  Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships

  摘要：

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.

  DOI：

  10.1021/jm010272s
• 作为产物：
  描述：

  溴甲苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 rac-N-benzyl-N-methylserine methyl ester
  参考文献：
  名称：

  β-羟基-α-氨基酯的脱氧放射性氟化反应：轻度条件下[18F]氟氨基酯的进入

  摘要：

  使用[ 18 F]氟化物阴离子在室温下成功实现了β-羟基-α-氨基酯的脱氧氟化。该反应涉及叠氮基中间体，并以良好的放射化学收率产生了相应的[ 18 F]氟化α或β-氨基酯。区域选择性取决于取代基R 1 -R 4的性质。

  DOI：

  10.1002/ejoc.201900300

文献信息

• Radical 1,4‐Aryl Migration Enabled Remote Cross‐Electrophile Coupling of α‐Amino‐β‐Bromo Acid Esters with Aryl Bromides
  作者：Shi Tang、Zhen‐Hua Xu、Ting Liu、Shuo‐Wen Wang、Jian Yu、Jian Liu、Yu Hong、Shi‐Lu Chen、Jin He、Jin‐Heng Li

  DOI：10.1002/anie.202106273

  日期：2021.9.20

  two new C(sp3)−C(sp2) bonds using a bench-stable Ni/bipyridine/Zn system featuring a broad substrate scope and excellent diastereoselectivity, which provides an effective platform for the remote aryl group migration and arylation of amino acid esters via redox-neutral C(sp3)−C(sp2) bond cleavage. Mechanistically, this cascade reaction is accomplished by combining two powerful catalytic cycles consisting

  我们报告了一种前所未有的、高效的镍催化自由基中继，用于通过 1,4-芳基迁移/芳基化级联将 β-溴-α-苄基氨基酸酯与芳基溴进行远程交叉亲电偶联。β-溴-α-苄基氨基酸酯被认为是独特的分子支架，允许芳基迁移反应，这是自由基休战-微笑重排的概念新变体。该反应能够使用具有广泛底物范围和优异非对映选择性的长期稳定的 Ni/联吡啶/Zn 系统形成两个新的 C(sp 3 )-C(sp 2 ) 键，为远程芳基提供了一个有效的平台氨基酸酯通过氧化还原中性 C(sp 3 )-C(sp 2 ) 的迁移和芳基化) 键断裂。机械地，该级联反应由通过C（SP的产生相结合自由交亲电耦合和自由基1,4-芳迁移的两个强大的催化循环实现3）-centred从C的均裂自由基中间体（SP 3） -Br 键和瞬态烷基自由基转换为强大的 α-氨基烷基自由基。
• Cysteine Derivatives as Inhibitors for Carboxypeptidase A:  Synthesis and Structure−Activity Relationships
  作者：Jung Dae Park、Dong H. Kim

  DOI：10.1021/jm010272s

  日期：2002.2.1

  A series of cysteine (Cys) derivatives having an alkyl or arylalkyl moiety on the a-amino group of the amino acid have been synthesized as a novel type of inhibitor for carboxypeptidase A. These compounds are readily prepared starting with Cys in an optically active form. The structure-activity relationship study revealed that the inhibitors prepared from D-Cys are much more potent than the corresponding inhibitors obtained from L-CYS, and the most potent inhibitor in the series, (S)-1j with a K-i value of 55 +/- 4 nM, is obtained by introducing a phenethyl moiety on the amino group Of D-CyS. In comparison, the most active inhibitor in the series of 2-substituted 3-mercaptopropanoic acid is found to be 20, in which the phenyl ring is linked to the mercaptocarboxylic acid at the a-position with a methylene unit. A proposal that accounts for the different structural requirement for the maximum activity between the two series of inhibitors is provided.
• Deoxyradiofluorination Reaction from β-Hydroxy-α-aminoesters: an Entry to [¹⁸ F]Fluoroaminoesters under Mild Conditions
  作者：Marine Morlot、Fabienne Gourand、Cécile Perrio

  DOI：10.1002/ejoc.201900300

  日期：2019.6.23

  Deoxyradiofluorination of β‐hydroxy‐α‐aminoesters was successfully achieved at room temperature using [18F]fluoride anion. The reaction involved an aziridinium intermediate and yielded the corresponding [18F]fluorinated α or β‐aminoesters in good radiochemical yields. Regioselectivity was dependent on the nature of substituents R1–R4.

  使用[ 18 F]氟化物阴离子在室温下成功实现了β-羟基-α-氨基酯的脱氧氟化。该反应涉及叠氮基中间体，并以良好的放射化学收率产生了相应的[ 18 F]氟化α或β-氨基酯。区域选择性取决于取代基R 1 -R 4的性质。