(R)-3-amino-2-phenylpropanoic acid

• 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)-3-amino-2-phenylpropanoic acid
• 英文别名: (2R)-3-azaniumyl-2-phenylpropanoate
• 化学式: C₉H₁₁NO₂
• 分子量: 165.192
• InChiKey: LRCYAJZPDFSJPQ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5,5-二甲基-2-苯基-1,3,2-二氧硼杂 在 bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)] 、 1,3-bis(2,6-diisopropylphenyl)-4,5-bis(dimethylamino)imidazolium triflate 、 氢溴酸 、 sodium carbonate 、 sodium t-butanolate 、 苯酚 作用下， 以 水 、 甲苯 为溶剂， 反应 24.0h， 生成 (R)-3-amino-2-phenylpropanoic acid
  参考文献：
  名称：

  Pd催化的对映体特异性和区域选择性开环铃木-宫浦芳基化氮丙啶-2-羧酸酯的不对称合成β2-芳基氨基酸

  摘要：

  开发了钯催化的对映体特异性和区域选择性开环的Aziridine-2-羧酸盐的Suzuki-Miyaura芳基化反应。交叉耦合允许对映体富集的β不对称制备2 -芳基氨基酸，从可商购的对映体纯起始d -和升-丝氨酸酯。基于计算模型对反应的机理和选择性进行了合理化。

  DOI：

  10.1002/chem.201902009

文献信息

• Enantioselective synthesis of 2-substituted 3-aminopropanoic acid (β-alanine) derivatives which are β-analogues of aromatic amino acids
  作者：Elena Arvanitis、Holger Ernst、Alice A. LudwigéD’Souza、Andrew J. Robinson、Peter B. Wyatt

  DOI：10.1039/a706163c

  日期：——

  3-Aminopropanoic acid derivatives with a phenyl, 4-hydroxyphenyl, benzyl or indol-3-yl substituent at C-2 can be prepared enantioselectively by routes involving electrophilic attack of synthetic equivalents of [H2NCH2]+ upon enolates derived from chiral 3-acyl-1,3-oxazolidin-2-ones. tert-Butyl bromoacetate may be used as the electrophile, with subsequent introduction of nitrogen through the Curtius reaction, using the sequence of reagents (i) CF3CO2H; (ii) (PhO)2P(O)N3, Et3N, PhCH2OH; alternatively, direct electrophilic reaction with 1-[N-(benzyloxycarbonyl)aminomethyl]benzotriazole 4c or benzyl N-(acetoxymethyl)carbamate 2d introduces a protected aminomethyl group in a single step.

  具有苯基、4-羟基苯基、苄基或吲哚-3-基的C-2取代基的3-氨基丙酸衍生物可以通过涉及合成[H2NCH2]+的亲电攻击的路线，从手性3-酰基-1,3-恶唑烷-2-酮衍生的烯醇盐选择性地制备。可以使用叔丁基溴乙酸酯作为亲电试剂，随后通过Curtius反应引入氮，使用试剂序列（i）CF3CO2H；（ii）(PhO)2P(O)N3，Et3N，PhCH2OH；或者，直接与1-[N-(苄氧羰基)氨基甲基]苯并三唑4c或苄基N-(乙酸甲酯)氨基甲酸酯2d进行亲电反应，一步引入保护的氨基甲基基团。
• Enantiopure<i>N</i>-Benzyloxycarbonyl-β²-amino Acid Allyl Esters from Racemic β-Lactams by Dynamic Kinetic Resolution using<i>Candida antarctica</i>Lipase B
  作者：Eleonora Gianolio、Resmi Mohan、Albrecht Berkessel

  DOI：10.1002/adsc.201500820

  日期：2016.1.7

  The dynamic kinetic resolution of α‐substituted racemic β‐lactams by alcoholytic ring‐opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic α‐substituted N‐Cbz‐azetidinones (Cbz=benzyloxycarbonyl) was transformed to the corresponding N‐Cbz‐protected β2‐amino acid allyl esters with high enantioselectivity (up to 99%) and high yields

  描述了由固定化的南极假丝酵母脂肪酶B催化的醇取代的开环反应，动态地分解了α-取代的外消旋β-内酰胺。与此过程中，各种外消旋α取代的Ñ -Cbz -氮杂环丁酮基（Cbz =苄）转化成相应的Ñ -Cbz保护的β 2个高对映选择性（高达99％）和高收率氨基酸烯丙基酯（最高定量）在室温下。
• Organocatalytic enantioselective Michael addition of a kojic acid derivative to nitro olefins
  作者：Jiyu Wang、Qing Zhang、Hui Zhang、Yujun Feng、Weicheng Yuan、Xiaomei Zhang

  DOI：10.1039/c2ob07192d

  日期：——

  By employing a chiral bifunctional thiourea–tertiary amine as catalyst, enantioselective Michael addition of a kojic acid derivative to nitro olefins was realised. The reactions afforded the products with good yields (up to 99%) in good enantioselectivities (up to 97% ee). In addition, the absolute configuration of one product was determined.

  通过采用手性双官能团 硫脲以叔胺为催化剂，实现了将曲酸衍生物对硝基烯烃的对映选择性迈克尔加成反应。反应提供了具有良好对映选择性（高达97％ee）的良好产率（高达99％）的产物。另外，确定一种产品的绝对构型。
• RAPAFUCIN DERIVATIVE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：The Johns Hopkins University

  公开号：US20210094933A1

  公开（公告）日：2021-04-01

  The present disclosure provides macrocyclic compounds inspired by the immunophilin ligand family of natural products FK506 and rapamycin. The generation of a Rapafucin library of macrocyles that contain FK506 and rapamycin binding domains should have great potential as new leads for developing drugs to be used for treating diseases.

  本公开提供了受免疫蛋白配体家族FK506和雷帕霉素天然产物启发的大环化合物。生成包含FK506和雷帕霉素结合结构域的Rapafucin大环化合物库，应具有作为治疗疾病新药的潜力。
• Palladium-catalysed asymmetric allylic substitution: synthesis of α- and β-amino acids
  作者：Justin F. Bower、Roshan Jumnah、Andrew C. Williams、Jonathan M. J. Williams

  DOI：10.1039/a606586d

  日期：——

  Methodology has been established for the formation of enantiomerically enriched α-amino acids using palladium-catalysed allylic amination. The formation of enantiomerically enriched allylamines has been achieved with high enantioselectivity. Oxidative cleavage of the allylamines provides arylglycine and glutamic acid derivatives. Additionally, enantiomerically enriched β-amino acids have been prepared in high enantiomeric excess. Palladium-catalysed asymmetric allylic substitution is used as the key synthetic transformation.

  利用钯催化的烯丙基胺化作用生成对映体丰富的δ-氨基酸的方法已经确立。以高对映选择性生成了对映体丰富的烯丙基胺。烯丙基胺的氧化裂解提供了芳基甘氨酸和谷氨酸衍生物。此外，还制备出了对映体丰度很高的δ-氨基酸。钯催化的不对称烯丙基置换是合成转化的关键。