(R)-2-Allyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester | 147240-40-2

• 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)-2-Allyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester
• 英文别名: methyl (2R)-5-methyl-2-propan-2-yl-2-(prop-2-enoxycarbonylamino)hex-4-enoate
• CAS: 147240-40-2
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: VINWSGLTKPDHJY-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-2-Allyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester 在 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 5,5-二甲基-1,3-环己二酮 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 41.17h， 生成 (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017
• 作为产物：
  描述：

  在 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 353.75h， 生成 (R)-2-Allyloxycarbonylamino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester
  参考文献：
  名称：

  De Novo Design, Synthesis, and X-ray Crystal Structures of Pyrrolinone-Based .beta.-Strand Peptidomimetics

  摘要：

  The de novo design and synthesis of a novel non-peptide scaffolding for beta-strand/sheet mimics are described. The scaffold consists of repeating 3,5,5-trisubstituted pyrrolinone (enaminone) units punctuated with appropriate amino acid side chains. The iterative construction of the pyrrolinones exploits a highly efficient cyclization of metalloimines, the latter derived from C-terminal aldehydes and readily available alpha-substituted alpha-amino ester building blocks. As predicted by interactive computer modeling and confirmed by X-ray crystallography, the polypyrrolinones present the side chains and carbonyl hydrogen-bond accepters in a solid-state conformation which mimics polypeptide beta-sheets. Importantly, the enaminone NH protons form hydrogen bonds both intramolecularly, stabilizing the beta-strand conformation, and intermolecularly, promoting sheet formation. The presence or absence of the nitrogen protecting group controlled antiparallel versus parallel sheet formation.

  DOI：

  10.1021/ja00101a017

文献信息

• ETHYNYLBENZENE DERIVATIVES
  申请人：Zhou Pei

  公开号：US20130231323A1

  公开（公告）日：2013-09-05

  Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R 1 , R 2 , R 3 , R 101 , L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.

  本发明涉及式(I)、(II)和(II)I的化合物及其药学上可接受的盐，其中变量R、R1、R2、R3、R101、L、D、Q、Y、X和Z的定义如下。这些化合物可用于治疗革兰氏阴性菌感染。
• [EN] ETHYNYLBENZENE DERIVATIVES<br/>[FR] DÉRIVÉS D'ÉTHYNYLE BENZÈNE
  申请人：UNIV DUKE

  公开号：WO2012031298A3

  公开（公告）日：2012-09-27
• An effective synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones
  作者：Amos B. Smith、Ryan C. Holcomb、Mark C. Guzman、Terence P. Keenan、Paul A. Sprengeler、Ralph Hirschmann

  DOI：10.1016/s0040-4039(00)60058-8

  日期：1993.1

  A new two-step method employs the intramolecular cyclization of metalated imino esters for the construction of scalemic 3,5,5-trisubstituted pyrrolin-4-ones (4). The imino esters in turn derive from alpha-disubstituted amino acids, the latter readily available via a new protocol exploiting the enantioretentive alkylation of oxazolidinones.
• Ethynylbenzene Derivatives
  申请人：Duke University

  公开号：US20170349544A1

  公开（公告）日：2017-12-07

  Disclosed are compounds of formulae (I), (II), and (II)I: and pharmaceutically acceptable salts thereof, wherein the variables, R, R 1 , R 2 , R 3 , R 101 , L, D, Q, Y, X, and Z are defined herein. These compounds are useful for treating Gram-negative bacteria infections.
• US9738604B2
  申请人：——

  公开号：US9738604B2

  公开（公告）日：2017-08-22