(R)-phenylalanine allyl ester | 361458-05-1

• 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)-phenylalanine allyl ester
• 英文别名: prop-2-enyl (2R)-2-amino-3-phenylpropanoate
• CAS: 361458-05-1
• 化学式: C₁₂H₁₅NO₂
• 分子量: 205.257
• InChiKey: CDFATPKAADNQOR-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (R)-phenylalanine allyl ester 、 Fmoc-glycinal 在 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  DNA-Templated Polymerization of Side-Chain-Functionalized Peptide Nucleic Acid Aldehydes

  摘要：

  The DNA-templated polymerization of synthetic building blocks provides a potential route to the laboratory evolution of sequence-defined polymers with structures and properties not necessarily limited to those of natural biopolymers. We previously reported the efficient and sequence-specific DNA-templated polymerization of peptide nucleic acid (PNA) aldehydes. Here, we report the enzyme-free, DNA-templated polymerization of side-chain-functionalized PNA tetramer and pentamer aldehydes. We observed that polymerization of tetramer and pentamer PNA building blocks with a single lysine-based side chain at various positions in the building block could proceed efficiently and sequence specifically. In addition, DNA-templated polymerization also proceeded efficiently and in a sequence-specific manner with pentamer PNA aldehydes containing two or three lysine side chains in a single building block to generate more densely functionalized polymers. To further our understanding of side-chain compatibility and expand the capabilities of this system, we also examined the polymerization efficiencies of 20 pentamer building blocks each containing one of five different side-chain groups and four different side-chain regio- and stereochemistries. Polymerization reactions were efficient for all five different side-chain groups and for three of the four combinations of side-chain regio- and stereochemistries. Differences in the efficiency and initial rate of polymerization correlate with the apparent melting temperature of each building block, which is dependent on side-chain regio- and stereochemistry but relatively insensitive to side-chain structure among the substrates tested. Our findings represent a significant step toward the evolution of sequence-defined synthetic polymers and also demonstrate that enzyme-free nucleic acid-templated polymerization can occur efficiently using substrates with a wide range of side-chain structures, functionalization positions within each building block, and functionalization densities.

  DOI：

  10.1021/ja0753997
• 作为产物：
  描述：

  Boc-D-苯丙氨酸 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (R)-phenylalanine allyl ester
  参考文献：
  名称：

  Solid-Phase Synthesis of Piperazinones via Disrupted Ugi Condensation

  摘要：

  The first application of aziridine aldehyde dimers in solid-phase synthesis is reported. The solid-supported disrupted Ugi condensation between an aziridine aldehyde dimer, isonitrile, and backbone-anchored amino acids delivered N-acyl aziridine intermediates, which were reacted with nucleophiles to yield the corresponding piperazinones. Subsequent cleavage from the resin provided a diverse set of 2,3,6-trisubstituted piperazinones starting from various amino acids, aziridine aldehydes, and nucleophiles.

  DOI：

  10.1021/ol5023118

文献信息

• [EN] A PROCESS FOR THE PREPARATION OF NATEGLINIDE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE NATÉGLINIDE
  申请人：CIPLA LTD

  公开号：WO2011157986A1

  公开（公告）日：2011-12-22

  The present invention relates to a process for the preparation of substantially pure nateglinide of formula (I), substantially free from the cis-isomer and L-enantiomer and preparation of enantiomerically pure nateglinide form B, directly from the hydrolysis of a (-)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-D-phenylalanine alkyl ester in a ketonic solvent or water or mixture thereof.

  本发明涉及一种制备几乎纯的分子式（I）的那格列奈的方法，该方法基本上不含顺式异构体和L-对映体，并且直接从对映纯的那格列奈B形式的制备，通过在酮溶剂或水或二者混合物中水解（-）-N-(反式-4-异丙基环己基-1-羰基)-D-苯丙氨酸烷基酯制备。
• Process for the Preparation of Nateglinide
  申请人：Kankan Rajendra Narayanrao

  公开号：US20130165686A1

  公开（公告）日：2013-06-27

  The present invention relates to a process for the preparation of substantially pure nateglinide of formula (I), substantially free from the cis-isomer and L-enantiomer and preparation of enantiomerically pure nateglinide form B, directly from the hydrolysis of a (−)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-D-phenylalanine alkyl ester in a ketonic solvent or water or mixture thereof.

  本发明涉及一种制备基本纯的nateglinide（I）的方法，基本上不含顺式异构体和L-对映体，并且直接从（-）-N-（反-4-异丙基环己基-1-羰基）-D-苯丙氨酸烷基酯在酮溶剂或水或其混合物中水解制备对映纯的nateglinide B的方法。
• Carboxylic acid derivatives as IP antagonists
  申请人：——

  公开号：US20010056100A1

  公开（公告）日：2001-12-27

  This invention relates to compounds which are generally IP receptor antagonists and which are represented by Formula I: 1 wherein: R 1 , R 2 , and R 3 are each independently in each occurrence aryl or heteroaryl; R 4 is —COOH or tetrazolyl; A, B, m, n, and r are as defined in the specification; or individual isomers, racemic or non-racemic mixtures of isomers, or pharmaceutically acceptable salts or solvates thereof. The invention further relates to pharmaceutical compositions containing such compounds, methods for their use as therapeutic agents, and processes for their preparation.

  本发明涉及一种通常为IP受体拮抗剂的化合物，其由公式I表示：1其中：R1、R2和R3在每次出现时各自独立地为芳基或杂环芳基；R4为—COOH或四唑基；A、B、m、n和r如规范中所定义；或其单一异构体、外消旋或非外消旋异构体混合物，或其药学上可接受的盐或溶剂。本发明还涉及含有这种化合物的制药组合物，以及将其用作治疗剂的方法和制备它们的过程。
• Production of N-acyl compounds
  申请人：Braun Max

  公开号：US20060217533A1

  公开（公告）日：2006-09-28

  A process for producing a compound containing an acylated nitrogen atom in which the adduct compound formed from an N-protonated cation and a chloride, bromide or iodide anion or the free nitrogen base is reacted with an acyl halide, preferably an acyl chloride, in the presence of an acid that drives off the released hydrogen chloride (HCl), hydrogen bromide (HBr) or hydrogen iodide (HI).

  一种生产含有酰化氮原子的化合物的工艺，其中由 N-质子化阳离子和氯化物、溴化物或碘化物阴离子或游离氮基形成的加合物与酰基卤化物（最好是酰基氯化物）在一种酸的存在下反应，该酸能驱除释放出的氯化氢（HCl）、溴化氢（HBr）或碘化氢（HI）。
• A PROCESS FOR THE PREPARATION OF NATEGLINIDE
  申请人：Cilpa Limited

  公开号：EP2580188A1

  公开（公告）日：2013-04-17