(±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate | 603944-76-9

• 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: (±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate
• 英文别名: (RS)-2-naphthylalanine ethyl ester；Ethyl 2-amino-3-naphthalen-2-ylpropanoate
• CAS: 603944-76-9
• 化学式: C₁₅H₁₇NO₂
• mdl: MFCD05228098
• 分子量: 243.305
• InChiKey: WMWUVPBDJARXRB-UHFFFAOYSA-N

物化性质

• 沸点：
  380.7±22.0 °C(Predicted)
• 密度：
  1.139±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.266
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate 在 吡啶 、 palladium diacetate 、 potassium carbonate 、 1-氟-2,4,6-三甲基吡啶三氟甲烷磺酸盐 作用下， 以 四氢呋喃 、 溶剂黄146 、 乙腈 为溶剂， 反应 52.0h， 生成 (±)-(E)-butyl 3-(3-(3-ethoxy-2-(N-methylpyridine-2-sulfonamido)-3-oxopropyl)naphthalen-2-yl)acrylate
  参考文献：
  名称：

  Pd-Catalyzed Directed ortho-C–H Alkenylation of Phenylalanine Derivatives

  摘要：

  A practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.

  DOI：

  10.1021/jo502912m
• 作为产物：
  描述：

  乙醇 、 DL-3-(2-萘基)丙氨酸 在 氯化亚砜 作用下， 反应 3.0h， 以79%的产率得到(±)-ethyl 2-amino-3-(naphthalen-2-yl)propanoate
  参考文献：
  名称：

  Pd-Catalyzed Directed ortho-C–H Alkenylation of Phenylalanine Derivatives

  摘要：

  A practical Pd-catalyzed ortho-olefination of enantioenriched N-(SO2Py)-protected aryl-alanine and norephedrine derivatives with electron-deficient alkenes has been developed using N-fluoro-2,4,6-trimethylpyridinium triflate as the terminal oxidant. The reaction occurs efficiently with excellent monosubstitution selectivity and without loss of enantiopurity. This cross-coupling proved to be broad in scope, tolerating a variety of steric and electronic changes to both coupling partners. Removal of the directing group under mild conditions provides access to optically active tetrahydroisoquinoline-3-carboxylic acid derivatives (Tics) with good diastereocontrol and with very small erosion of enantiomeric purity.

  DOI：

  10.1021/jo502912m

文献信息

• PROCESS FOR PREPARING OPTICALLY ACTIVE (S OR R)-ALPHA-AMINO ACID AND OPTICALLY ACTIVE (R OR S)-ALPHA-AMINO ACID ESTER
  申请人：Yamamoto Yasuhito

  公开号：US20090042260A1

  公开（公告）日：2009-02-12

  The present invention discloses a process for preparing an optically active (S or R)-α-amino acid represented by the formula (II): wherein R represents an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aralkyl group, heteroarylalkyl group, aryl group or heteroaryl group, each of which may have a substituent(s), and * represents an asymmetric carbon atom, and an optically active (R or S)-α-amino acid ester represented by the formula (III): wherein R 1 represents an alkyl group which may have a substituent(s), and * represents an asymmetric carbon atom, provided that it has an opposite absolute configuration to that of the compound of the formula (II), which comprises selectively reacting water with one of enantiomers of an α-amino acid ester which is a racemic mixture and represented by the formula (I): wherein R and R 1 have the same meanings as defined above, in the presence of a lipase or a protease in an organic solvent.

  本发明揭示了一种制备光学活性（S或R）-α-氨基酸的方法，其表示为式（II）：其中R表示烷基，烯基，炔基，环烷基，芳基烷基，杂芳基烷基，芳基或杂芳基，每个基团都可以有取代基，而*表示不对称碳原子；以及光学活性（R或S）-α-氨基酸酯，其表示为式（III）：其中R1表示烷基，可以有取代基，而*表示不对称碳原子，前提是它的绝对构型与式（II）的化合物相反；所述方法包括在有机溶剂中，在脂肪酶或蛋白酶的存在下，选择性地将水与由式（I）表示的混合的α-氨基酸酯的对映体之一反应，其中R和R1的含义如上所定义。
• Biphenyl aldehyde-based ternary catalytic system catalyzed Tsuji–Trost allylation of N-unprotected amino acid esters
  作者：Zhao-Wei Wu、Wei Wen、Qi-Xiang Guo

  DOI：10.1016/j.tet.2022.133235

  日期：2023.2

  the direct α-allylation reaction of N-unprotected amino acid esters and allyl alcohol acetates. The chemoselectivity of C-allylation and N-allylation is efficiently controlled and various racemic α,α-disubstituted amino acid esters are generated in good-to-high yields. The target products can be readily converted into structurally diverse α,α-disubstituted amino acids at a gram scale.

  合理设计了一种基于联苯醛的高效三元催化体系，并将其应用于N-未保护氨基酸酯和烯丙醇乙酸酯的直接α-烯丙基化反应。C-烯丙基化和N-烯丙基化的化学选择性得到有效控制，各种外消旋 α,α-二取代氨基酸酯的产率从好到高。目标产物可以很容易地以克级转化为结构多样的 α,α-二取代氨基酸。
• Core Structure-Oriented Asymmetric α-Allenylic Alkylation of Amino Acid Esters Enabled by Chiral Aldehyde/Palladium Catalysis
  作者：Hao Zhang、Wei Wen、Ze-Xi Lu、Zhu-Lian Wu、Tian Cai、Qi-Xiang Guo

  DOI：10.1021/acs.orglett.3c03762

  日期：2024.1.12

  to manzacidins A and D, here we report a highly efficient catalytic asymmetric α-allenylic alkylation reaction of NH2-unprotected amino acid esters that is promoted by combined chiral aldehyde/palladium catalysis. Fifty examples of unnatural α,α-disubstituted amino acid esters are reported with good-to-excellent yields and stereoselectivities. Based on this methodology, a key intermediate leading to

  针对已报道的生成manzacidins A和D的手性合成子，我们在此报道了一种由手性醛/钯联合催化促进的NH 2 -未保护的氨基酸酯的高效催化不对称α-丙烯基烷基化反应。据报道，非天然 α,α-二取代氨基酸酯的 50 个实例具有良好至优异的产率和立体选择性。基于该方法，相应地制备了曼扎西定C及其其他三种立体异构体的关键中间体。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE (S OR R)-a-AMINO ACID OR OPTICALLY ACTIVE (S OR R)-a -AMINO ACID ESTER
  申请人：Ube Industries, Ltd.

  公开号：EP1942193A1

  公开（公告）日：2008-07-09

  The present invention discloses a process for preparing an optically active (S or R)-α-amino acid represented by the formula (II): wherein R represents an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aralkyl group, heteroarylalkyl group, aryl group or heteroaryl group, each of which may have a substituent(s), and * represents an asymmetric carbon atom, and an optically active (R or S)-α-amino acid ester represented by the formula (III): wherein R1 represents an alkyl group which may have a substituent(s), and * represents an asymmetric carbon atom, provided that it has an opposite absolute configuration to that of the compound of the formula (II), which comprises selectively reacting water with one of enantiomers of an α-amino acid ester which is a racemic mixture and represented by the formula (I): wherein R and R1 have the same meanings as defined above, in the presence of a lipase or a protease in an organic solvent.

  本发明公开了一种制备由式（II）代表的光学活性（S 或 R）-α-氨基酸的工艺： 其中 R 代表烷基、烯基、炔基、环烷基、芳烷基、杂芳烷基、芳基或杂芳基，每个基团可以有一个或多个取代基，* 代表不对称碳原子、 以及由式（III）代表的光学活性（R 或 S）-α-氨基酸酯： 其中 R1 代表一个烷基，该烷基可以有一个或多个取代基，* 代表一个不对称碳原子，但其绝对构型必须与式 (II) 所示化合物的绝对构型相反、 其中包括选择性地使水与α-氨基酸酯的对映体之一反应，α-氨基酸酯是外消旋混合物，由式（I）表示： 其中 R 和 R1 的含义与上述定义相同、 在脂肪酶或蛋白酶存在下，在有机溶剂中进行。
• Enantioselective Tsuji‐Trost α‐Fluoroallylation of Amino Acid Esters with <i>Gem</i>‐Difluorinated Cyclopropanes
  作者：Zheng Su、Binhong Tan、Hui He、Kaifeng Chen、Shixin Chen、Hongtao Lei、Tie‐Gen Chen、Shao‐Fei Ni、Zhaodong Li

  DOI：10.1002/anie.202402038

  日期：——

  aldehyde synergistic relay system was developed for the enantioselective ring-opening functionalization of gem-difluorinated cyclopropanes with N-unprotected amino acid esters, enabling the efficient assembly of α-quaternary α-amino acid esters bearing a linear 2-fluoroallylic motif in a highly enantioselective manner.

  开发了一种强大的钯/镍/手性醛协同中继系统，用于用 N-未保护的氨基酸酯对偕二氟化环丙烷进行对映选择性开环官能化，从而能够有效组装带有线性 2 的 α-季铵 α-氨基酸酯。 -氟烯丙基基序以高度对映选择性的方式。