methyl (2R)-2-amino-5-methyl-2-propan-2-ylhex-4-enoate | 145452-08-0

• 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: methyl (2R)-2-amino-5-methyl-2-propan-2-ylhex-4-enoate
• CAS: 145452-08-0
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: GTHHCCBDDYVILE-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  methyl (2R)-2-amino-5-methyl-2-propan-2-ylhex-4-enoate 在 sodium periodate 、 四氧化锇 、 双(三甲基硅烷基)氨基钾 、 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 25.59h， 生成 (S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-5'-(3-methyl-but-2-enyl)-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-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：

  (2R,4R)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 四(三苯基膦)钯 sodium hydroxide 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 5,5-二甲基-1,3-环己二酮 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.5h， 生成 methyl (2R)-2-amino-5-methyl-2-propan-2-ylhex-4-enoate
  参考文献：
  名称：

  An effective synthesis of scalemic 3,5,5-trisubstituted pyrrolin-4-ones

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)60058-8

文献信息

• Molecular modeling, synthesis, and structures of N-methylated 3,5-linked pyrrolin-4-ones toward the creation of a privileged nonpeptide scaffold
  作者：Amos B. Smith III、David A. Favor、Paul A. Sprengeler、Mark C. Guzman、Patrick J. Carroll、George T. Furst、Ralph Hirschmann

  DOI：10.1016/s0968-0896(98)00234-x

  日期：1999.1

  three predicted backbone conformers (ca. 165 degrees and 289 degrees). Two structures were particularly noteworthy and completely unexpected. Mono-N-methyl bispyrrolinone (+)-1 self assembled in the solid state to form a novel helix, while the acetylene-linked dimer of (+)-1, designed to potentiate the observed helical array, instead associated via an intermolecular hydrogen bond in parallel columns. These

  描述了N-甲基化3,5-连接的双吡咯啉-4-酮的固态和溶液结构的分子建模，合成和阐明。先前的研究证实，可以将基于3,5-联结的吡咯烷-4-one的支架掺入β-sheet/β链的模拟物中，并掺入有效的，可口服的HIV-1蛋白酶抑制剂中。为了将这种支架的效用扩展到最初设计的β-折叠/β-链模拟物之外，我们现在探索了N-甲基化吡咯烷酮的结构。分子模型表明，N-甲基化的双吡咯啉酮可采用三种低能主链构象（约165度，289度和320度）。成功合成之后，固态和溶液中的结构解析都揭示了三个预测的骨架构象异构体中的两个（约165度和289度）的存在。两种结构特别值得注意，完全出乎意料。单-N-甲基双吡咯啉酮（+）-1以固态自组装形成新的螺旋，而（+）-1的乙炔连接的二聚体旨在增强观察到的螺旋排列，而不是通过分子间氢缔合在平行列中键合。这些偶然的发现使我们推测吡咯烷酮部分实际上可以代表一种特权的非肽支架，不
• A Second-Generation Synthesis of Polypyrrolinone Nonpeptidomimetics:  Prelude to the Synthesis of Polypyrrolinones on Solid Support
  作者：Amos B. Smith、Hu Liu、Ralph Hirschmann

  DOI：10.1021/ol0059293

  日期：2000.7.1

  [reaction: see text] A second-generation asymmetric synthesis of polypyrrolinones (3) has been achieved exploiting scalemic alpha-aminolactones (1) as building blocks. Imine formation between an appropriate lactone (1) and aldehyde (2), followed in turn by pyrrolinone ring construction promoted by KHMDS in the presence of 18-crown-6 and modified Swern oxidation furnished pyrrolinone aldehyde 3. This iterative

  [反应：见正文]利用垢型α-氨基内酯（1）作为结构单元，已经实现了第二代不对称合成的聚吡咯烷酮（3）。在适当的内酯（1）和醛（2）之间形成亚胺，然后依次在18-crown-6和修饰的Swern氧化作用下，由KHMDS促进吡咯烷酮环的构建，从而得到吡咯烷酮醛3。这种迭代，有效的三步法该方案为在固体载体上合成聚吡咯烷酮铺平了道路。
• 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
• Design, synthesis, and crystal structure of a pyrrolinone-based peptidomimetic possessing the conformation of a .beta.-strand: potential application to the design of novel inhibitors of proteolytic enzymes
  作者：Amos B. Smith、Terence P. Keenan、Ryan C. Holcomb、Paul A. Sprengeler、Mark C. Guzman、John L. Wood、Patrick J. Carroll、Ralph Hirschmann

  DOI：10.1021/ja00052a093

  日期：1992.12