(2R,4R)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester | 147240-31-1

• 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: (2R,4R)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
• 英文别名: prop-2-enyl (2R,4R)-2-tert-butyl-5-oxo-4-propan-2-yl-1,3-oxazolidine-3-carboxylate
• CAS: 147240-31-1
• 化学式: C₁₄H₂₃NO₄
• 分子量: 269.341
• InChiKey: OPSLPNZIQCELCU-ZYHUDNBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester 在 sodium hydroxide 、 sodium periodate 、 四氧化锇 、 四(三苯基膦)钯 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 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 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 58.92h， 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：

  L-缬氨酸 在 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 360.5h， 生成 (2R,4R)-2-tert-Butyl-4-isopropyl-5-oxo-oxazolidine-3-carboxylic acid allyl ester
  参考文献：
  名称：

  [EN] ETHYNYLBENZENE DERIVATIVES
  [FR] DÉRIVÉS D'ÉTHYNYLE BENZÈNE

  摘要：

  公开号：

  WO2012031298A3

文献信息

• Enantioretentive alkylation of oxazolidinone aluminum enolates with epoxides: Preparation of uncoded homoserine analogs
  作者：Amos B. Smith、Alexander Pasternak、Akihisa Yokoyama、Ralph Hirschmann

  DOI：10.1016/0040-4039(94)88404-8

  日期：1994.11

  The alkylation of Karady/Seebach oxazolidinone enolates with epoxides, promoted by 2.1 equivalents of diethylaluminum chloride, furnishes ring-opened adducts in moderate-to-good yields with high diastereoselectivity. The method provides an effective approach to uncoded homoserine analogs and expands the utility of readily available oxazolidinones in asymmetric synthesis.

  Karady / Seebach恶唑烷酮烯醇烯酸酯与环氧化物的烷基化，由2.1当量的二乙基氯化铝促进，以中等至良好的收率和高非对映选择性提供开环加合物。该方法为未编码的高丝氨酸类似物提供了有效的方法，并扩大了不对称合成中容易获得的恶唑烷酮的实用性。
• 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
• 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。
• 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.
• Pyrrolinone-Based HIV Protease Inhibitors. Design, Synthesis, and Antiviral Activity: Evidence for Improved Transport
  作者：Amos B Smith、Ralph Hirschmann、Alexander Pasternak、Mark C. Guzman、Akihisa Yokoyama、Paul A. Sprengeler、Paul L. Darke、Emilio A. Emini、William A. Schleif

  DOI：10.1021/ja00150a011

  日期：1995.11

  Pyrrolinone-based peptidomimetics, the first mimics of beta-strands, are potent inhibitors of HIV-1 protease. Importantly, the bis(pyrrolinones) described herein proved to be more active in cellular antiviral assays compared with an analogous peptide-derived inhibitor even though they are less effective in inhibiting the isolated protease. These results suggest that pyrrolinone inhibitors offer better transport properties than the corresponding peptide-based peptidomimetics; we attribute this effect to decreased solvation of the mimetics. Structure-activity relationships for the pyrrolinones correlate well with those reported for related peptides, consistent with similar modes of binding.