(4R)-4-isopropyl-3-(4-pentenoyl)oxazolidin-2-one | 367250-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: (4R)-4-isopropyl-3-(4-pentenoyl)oxazolidin-2-one
• 英文别名: (4R)-4-isopropyl-3-pent-4-enoyl-oxazolidin-2-one；(4R)-isopropyl-3-pent-4-enoyl-oxazolidin-2-one；(4R)-3-pent-4-enoyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 367250-92-8
• 化学式: C₁₁H₁₇NO₃
• 分子量: 211.261
• InChiKey: KGVIGZKSYUPUIP-VIFPVBQESA-N

物化性质

• 沸点：
  328.3±21.0 °C(Predicted)
• 密度：
  1.081±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4R)-4-isopropyl-3-(4-pentenoyl)oxazolidin-2-one 在 4-二甲氨基吡啶 、 双氧水 、 四氯化钛 、 N,N-二异丙基乙胺 、 lithium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 6.5h， 生成 (S)-methyl 2-((benzyloxy)methyl)pent-4-enoate
  参考文献：
  名称：

  基于酸性神经酰胺酶活性的探针的开发。

  摘要：

  酸性神经酰胺酶负责将神经酰胺水解为鞘氨醇和游离脂肪酸，从而使（糖）鞘氨醇分解代谢中的最终步骤。酸性神经酰胺酶的缺乏是Farber疾病的分子基础。在这里，我们报告基于活性的酸性神经酰胺酶探针的合成和表征。

  DOI：

  10.1039/c5cc00356c
• 作为产物：
  描述：

  4-戊烯酰氯 、 (R)-(+)-4-异丙基-2-恶唑啉酮 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (4R)-4-isopropyl-3-(4-pentenoyl)oxazolidin-2-one
  参考文献：
  名称：

  基于酸性神经酰胺酶活性的探针的开发。

  摘要：

  酸性神经酰胺酶负责将神经酰胺水解为鞘氨醇和游离脂肪酸，从而使（糖）鞘氨醇分解代谢中的最终步骤。酸性神经酰胺酶的缺乏是Farber疾病的分子基础。在这里，我们报告基于活性的酸性神经酰胺酶探针的合成和表征。

  DOI：

  10.1039/c5cc00356c

文献信息

• Analogues of Bleomycin:  Synthesis of Conformationally Rigid Methylvalerates
  作者：Michael J. Rishel、Sidney M. Hecht

  DOI：10.1021/ol010139u

  日期：2001.9.1

  Several conformationally rigid analogues of the methylvalerate subunit contained within the linker domain of the antitumor antibiotic bleomycin have been prepared. These compounds have been protected in a fashion suitable for the solid-phase synthesis of bleomycin. Bleomycin congeners containing these analogues should facilitate a more detailed understanding of the nature of the conformational bend that

  [结构：见文字]。已经制备了抗肿瘤抗生素博来霉素的接头域内所含的几种戊酸甲酯亚基的构象刚性类似物。这些化合物已经以适用于博来霉素固相合成的方式得到了保护。含有这些类似物的博来霉素同类物应有助于更详细地理解认为戊酸甲酯部分赋予天然产物的构象弯曲的性质。
• Synthesis of 3,4,5-trisubstituted piperidine via S_N2’ reaction
  作者：Fei Li、Xue Wang、Yue Meng Liu、Jing Zhang、Jun Yang

  DOI：10.1080/00397911.2019.1682612

  日期：2020.1.2

  of biological activities, are potential drug candidates to treatment of Alzheimer’s disease, sexual dysfunctions or obesity, heart and kidney insufficiency. However, the inherent difficulty in obtaining a variety of 3,4,5-trisubstituted piperidines has greatly hindered their systematic medicinal chemistry studies for them. In this paper, we disclose an efficient synthesis of racemic and chiral 3,4,5-trisubstituted

  摘要 含有 3,4,5-三取代哌啶的化合物显示出一系列生物活性，是治疗阿尔茨海默病、性功能障碍或肥胖症、心肾功能不全的潜在候选药物。然而，获得各种3,4,5-三取代哌啶的固有困难极大地阻碍了他们对它们进行系统的药物化学研究。在本文中，我们公开了一种通过 SN2' 反应有效合成外消旋和手性 3,4,5-三取代哌啶的方法。图形概要
• Dual-Acting Thromboxane Receptor Antagonist/Synthase Inhibitors: Synthesis and Biological Properties of [2-Substituted-4-(3-pyridyl)-1,3-dioxan-5-yl]alkenoic Acids
  作者：Alan W. Faull、Andrew G. Brewster、George R. Brown、Michael J. Smithers、Ruth Jackson

  DOI：10.1021/jm00004a014

  日期：1995.2

  The design, synthesis, and pharmacology of a new class of compounds possessing both thromboxane receptor antagonist and thromboxane synthase inhibitory properties are described. Replacement of the phenol group of the known thromboxane antagonist series 4(Z)-6-[(4RS,5SR)-4-(2-hydroxyphenyl)-1,3-dioxan-5-yl]hex-4-enoic acid by a 3-pyridyl group led to a series of compounds, 5, which were potent thromboxane synthase inhibitors and weak thromboxane antagonists. Further modifications at the dioxane C2 position led to compounds, 7, which were potent dual-acting agents. In the case of compound 7w, the dual activity was shown to reside almost exclusively in the (-)-enantiomer, 7x. Following oral dosing to rats and dogs, 7x (3 mg/kg) displayed significant dual activity over a period of at least 8 h.
• Conformationally Constrained Analogues of Bleomycin A₅
  作者：Michael J. Rishel、Craig J. Thomas、Zhi-Fu Tao、Corine Vialas、Christopher J. Leitheiser、Sidney M. Hecht

  DOI：10.1021/ja030057w

  日期：2003.8.1

  The bleomycin (BLM) group antitumor antibiotics are glycopeptide-derived natural products shown to cause sequence selective lesions in DNA. Prior studies have indicated that the linker region, composed of the methylvalerate and threonine residues, may be responsible for a conformational bend in the agent required for efficient DNA cleavage. We have synthesized a number of conformationally constrained methylvalerate analogues and incorporated them into deglycobleomycin A(5) congeners using our recently reported procedure for the solid phase construction of (deglyco)bleomycin and its analogues. These analogues were designed to probe the effects of conformational constraint of the native valerate moiety. Initial experiments indicated that the constrained molecules, none of which mimic the conformation proposed for the natural valerate linker, possessed DNA cleavage activity, albeit with potencies less than that of (deglyco)BLM and lacking sequence selectivity. Further experiments demonstrated that these analogues failed to produce alkali-labile lesions in DNA or sequence selective oxidative damage in RNA. However, two of the conformationally constrained deglycoBLM analogues were shown to mediate RNA cleavage in the absence of added Fe2+. The ability of the analogues to mediate the oxygenation of small molecules was also assayed, and it was shown that they were as competent in the transfer of oxygen to low molecular weight substrates as the parent compound.
• HETEROCYCLIC DERIVATIVES AND THEIR USE AS INTEGRIN INHIBITORS
  申请人：AstraZeneca AB

  公开号：EP1133484A2

  公开（公告）日：2001-09-19