D-alanine ethyl ester

• 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: D-alanine ethyl ester
• 英文别名: ethyl D-alaninate；D-Ala-OEt；ethyl (2R)-2-aminopropanoate
• 化学式: C₅H₁₁NO₂
• 分子量: 117.148
• InChiKey: ROBXZHNBBCHEIQ-SCSAIBSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  D-alanine ethyl ester 在 10% Nishimura catalyst <(45.9% Rh/19.9% Pt) oxide> 氢气 作用下， 以 甲醇 为溶剂， 25.0 ℃ 、10.0 MPa 条件下， 反应 16.0h， 生成 D-氨基丙醇
  参考文献：
  名称：

  Catalytic Hydrogenation of Chiral α-Amino and α-Hydroxy Esters at Room Temperature with Nishimura Catalyst without Racemization

  摘要：

  The hydrogenation or carboxylic acid derivatives at room temperature was investigated. With a mixed Rh/Pt oxide (Nishimura catalyst), low to medium activity was observed for various alpha-amino and alpha-hydroxy esters. At 100 bar hydrogen pressure and 10% catalysts loading, high yields or tire desired amino alcohols and diols were obtained without racemization. The most suitable alpha-substituents were NH2, NHR, and 011, whereas beta-NH2 were less effective. Usually, aromatic rings were also hydrogenated, but with the free bases of amino acids as substrates, some selectivity was observed. No reaction was round for alpha-NR2, alpha-OR, and unfunctionalized esters; acids and amides, were also not reduced under these conditions. A working hypothesis for the mode or action of the catalyst is presented.

  DOI：

  10.1002/1615-4169(20011231)343:8<802::aid-adsc802>3.0.co;2-t
• 作为产物：
  描述：

  丙氨酸乙酯 在 α-bromo-camphor-sulfonic acid-(ϖ) 、 水 作用下， 生成 D-alanine ethyl ester
  参考文献：
  名称：

  Colombano; Sanna; Delitala, Gazzetta Chimica Italiana, 1914, vol. 44 I, p. 102

  摘要：

  DOI：

文献信息

• 2'-AZIDO SUBSTITUTED NUCLEOSIDE DERIVATIVES AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
  申请人：Girijavallabhan Vinay

  公开号：US20140206640A1

  公开（公告）日：2014-07-24

  The present invention relates to 2′-Azido Substituted Nucleoside Derivatives of Formula (I): and pharmaceutically acceptable salts thereof, wherein B, X, R 1 , R 2 and R 3 are as defined herein. The present invention also relates to compositions comprising at least one 2′-Azido Substituted Nucleoside Derivative, and methods of using the 2′-Azido Substituted Nucleoside Derivatives for treating or preventing HCV infection in a patient.

  本发明涉及式(I)的2'-叠氮基取代核苷衍生物及其药学上可接受的盐，其中B、X、R1、R2和R3如本文所定义。本发明还涉及包含至少一种2'-叠氮基取代核苷衍生物的组合物，以及使用这些2'-叠氮基取代核苷衍生物治疗或预防患者HCV感染的方法。
• Reductive Alkylation of Amines with Carboxylic Ortho Esters
  作者：Renat Kadyrov、Konrad Moebus

  DOI：10.1002/adsc.202000510

  日期：2020.8.19

  carboxylic ortho esters could be used as an alkylating agent in the reductive alkylation of amines. A variety of amines, including amino acid esters, were alkylated affording mono‐alkylated products with high selectivity in practical to high yields using standard heterogeneous catalysts. By applying acyclic ortho esters alkylation was completed at room temperature.

  我们首次证明了羧酸原酸酯可以在胺的还原烷基化中用作烷基化剂。使用标准的多相催化剂，将多种胺（包括氨基酸酯）进行烷基化，从而以高产率实际可行地以高选择性生成单烷基化产物。通过施加无环原酸酯，在室温下完成烷基化。
• Redox-Neutral P(O)–N Coupling between P(O)–H Compounds and Azides via Dual Copper and Photoredox Catalysis
  作者：Yanan Wu、Ken Chen、Xia Ge、Panpan Ma、Zhiyuan Xu、Hongjian Lu、Guigen Li

  DOI：10.1021/acs.orglett.0c02207

  日期：2020.8.7

  We report a redox-neutral P(O)–N coupling reaction of P(O)–H compounds with azides via photoredox and copper catalysis, providing new access to useful phosphinamides, phosphonamides, and phosphoramides. This transformation tolerates a wide range of nucleophilic functionalities including alcohol and amine nucleophiles, which makes up for the deficiency of classical nitrogen nucleophilic substitution

  我们报道了P（O）-H化合物与叠氮化物通过光氧化还原和铜催化的氧化还原中性P（O）-N偶联反应，提供了获得有用的次膦酰胺，膦酰胺和磷酰胺的新途径。这种转化可耐受多种亲核功能，包括醇和胺亲核，这弥补了传统氮亲核取代反应的不足。为了证明这种新方法的广泛潜在应用，已开发了多种含叠氮基天然产物和药物分子的后期功能化，初步的不对称反应和连续的可见光光流过程。
• But-3-ene-1,3-disulfonyl difluoride (BDF): a highly selective SuFEx clickable hub for the quick assembly of sultam-containing aliphatic sulfonyl fluorides
  作者：Chen Li、Yujie Zheng、K. P. Rakesh、Hua-Li Qin

  DOI：10.1039/d0cc03248d

  日期：——

  3-disulfonyl difluoride (BDF) was designed and synthesized through head-to-tail dimerization of ethenesulfonyl fluoride (ESF). BDF possesses three active sites to selectively participate in the construction of 4-membered, 5-membered and 6-membered cyclic sulfonamide (sultams) bearing aliphatic sulfonyl fluoride moieties for further manipulations in a fast, efficient and practical manner.

  设计并开发了通用的可选择性寻址的SuFEx Click化学中心，但是通过乙磺酰氟（ESF）从头到尾的二聚化合成了3-ene-1,3-二磺酰二氟（BDF）。BDF具有三个活性位点，可选择性地参与带有脂肪族磺酰氟部分的4元，5元和6元环状磺酰胺（sultams）的构建，以便以快速，有效和实用的方式进行进一步操作。
• A new chiral glycine synthon. Synthesis, x-ray structure of (−).(2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine and diastereoselective nucleophilic ring opening to (R)-ethyl α-amino carboxylates.
  作者：Celia Andrés、Alfonso González、Rafael Pedrosa、Alfonso Pérez-Encabo、Santiago García-Granda、M.A. Salvadó、Fermín Gómez-Beltrán

  DOI：10.1016/s0040-4039(00)61274-1

  日期：1992.8

  Condensation of (R)-N-benzyl-2-phenylglycinol 1 with the methyl hemiacetal of ethyl glyoxylate leads to (2S,4R)-2-ethoxycarbonyl-4-phenyl-1,3-oxazolidine 2 as the major product, obtained as a pure enantiomer after column chromatography. Compound 2 is stereoselectively cleaved by dialkylzinc reagents, prepared from alkylmagnesium iodides and ZnCl2, with moderate to good d.e.ś (72–94 %). These compounds

  （R）-N-苄基-2-苯基甘氨醇的缩合1与乙醛酸乙酯引线的甲基半缩醛向（2S，4R）-2-乙氧羰基-4-苯基-1,3-恶唑烷2所获得作为主要产物，柱层析后得到纯对映体。化合物2被二烷基锌试剂立体选择性切割，该试剂由碘化烷基镁和ZnCl 2制备，中等至良好（72-94％）。这些化合物经柱色谱分离并在碳上含10％Pd的条件下通过氢解脱苄基作用后，得到对映体纯的α-氨基羧酸乙酯，具有良好的化学收率。