(R)-2-but-3-enyloxirane | 144422-60-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (R)-2-but-3-enyloxirane
• 英文别名: (R)-2-allyloxirane；(2R)-2-allyloxirane；(R)-allyloxirane；(2R)-2-prop-2-enyloxirane
• CAS: 144422-60-6
• 化学式: C₅H₈O
• 分子量: 84.1179
• InChiKey: SPXXVGQMQJYJJO-RXMQYKEDSA-N

物化性质

• 沸点：
  76.6±9.0 °C(Predicted)
• 密度：
  0.900±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  6
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-2-but-3-enyloxirane 在 吡啶 、 4-二甲氨基吡啶 、 copper(l) iodide 、 三氟化硼乙醚 、 水 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 31.17h， 生成
  参考文献：
  名称：

  Structure−Activity Relationship Studies of Novel Carbocyclic Influenza Neuraminidase Inhibitors

  摘要：

  A series of influenza neuraminidase inhibitors with the cyclohexene scaffold containing lipophilic side chains have been synthesized anti evaluated for influenza A and B neuraminidase inhibitory activity. The size and geometry of side chains have been modified systematically in order to investigate structure-activity relationships of this class of compounds. The X-ray crystal structures of several analogues complexed with neuraminidase revealed that the lipophilic side chains bound to the hydrophobic pocket consisted of Glu276, Ala246, Arg224, and Ile222 of the enzyme active site. The structure-activity relationship studies of this series have also demonstrated remarkably different inhibitory potency between influenza A and B neuraminidase. This indicated that the lipophilic side chains had quite different hydrophobic interactions with influenza A and B neuraminidase despite their complete homology in the active site. Influenza B neuraminidase appeared to be much more sensitive toward the increased steric bulkiness of inhibitors compared to influenza A neuraminidase. From the extensive structure-activity relationship investigation reported in this article, GS 4071 emerged as one of the most potent influenza neuraminidase inhibitors against both influenza A and B strains.

  DOI：

  10.1021/jm980162u
• 作为产物：
  描述：

  1,4-戊二烯 在 [(S,S-(C₆H₅)2PCH(CH₃)CH(CH₃)P(C₆H₅)2)Pt(pentafluorophenyl)(OH₂)]CF₃SO₃) 双氧水 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 以66%的产率得到(R)-2-but-3-enyloxirane
  参考文献：
  名称：

  五氟苯基PtII络合物催化过氧化氢不对称环氧化末端烯烃

  摘要：

  容易获得的手性 PtII 复合物 1 允许末端烯烃与过氧化氢的高度对映选择性和完全区域选择性不对称环氧化

  DOI：

  10.1021/ja0647607

文献信息

• Asymmetric Synthesis and Biological Activity of nor-α-Tocopherol, a New Vitamin E Analogue
  作者：Julien Chapelat、Urs Hengartner、Antoinette Chougnet、Kegang Liu、Patricia Huebbe、Gerald Rimbach、Wolf-D. Woggon

  DOI：10.1002/cbic.201000511

  日期：2011.1.3

  SARs of vitamins: (2R,4′R,8′R)‐nor‐α‐Tocopherol has been prepared from (all‐R)‐hexahydrofarnesol in high (94 %) diasteromeric excess, and (2RS,4′R,8′R)‐nor‐α‐tocopherol has beeen prepared from phytol. nor‐α‐Tocopherol displays excellent antiinflammatory properties in vitro.

  维生素特区：（2 - [R，4' - [R，8' - [R）-nor-α生育酚已经从（清一色制备- [R）-hexahydrofarnesol在高（94％）非对映体过量，和（2个RS，4' - [R，8' - [R）-nor-α生育酚已经beeen从植醇制备。nor-α-生育酚在体外显示出出色的抗炎特性。
• Quorum Sensing in Bacterial Species that Use Degenerate Autoinducers Can Be Tuned by Using Structurally Identical Non-native Ligands
  作者：Andrew G. Palmer、Evan Streng、Kelsea A. Jewell、Helen E. Blackwell

  DOI：10.1002/cbic.201000551

  日期：2011.1.3

  Talk this way: Different bacteria use identical quorum sensing (QS) signals to regulate important cell‐density dependent phenotypes. Herein, we show that non‐native compounds previously identified as QS modulators in one species can be reappropriated to regulate QS in alternate bacteria that utilize the same native signal. These results considerably broaden the species range of the known non‐native QS

  这样说吧：不同的细菌使用相同的群体感应 (QS) 信号来调节重要的细胞密度依赖性表型。在此，我们表明，先前在一个物种中被鉴定为 QS 调节剂的非天然化合物可以重新用于调节利用相同天然信号的替代细菌中的 QS。这些结果大大拓宽了已知的非天然 QS 调节剂的种类范围。
• Synthetic Access to the Mandelalide Family of Macrolides: Development of an Anion Relay Chemistry Strategy
  作者：Minh H. Nguyen、Masashi Imanishi、Taichi Kurogi、Xuemei Wan、Jane E. Ishmael、Kerry L. McPhail、Amos B. Smith

  DOI：10.1021/acs.joc.8b00268

  日期：2018.4.20

  The mandelalides comprise a family of structurally complex marine macrolides that display significant cytotoxicity against several human cancer cell lines. Presented here is a full account on the development of an Anion Relay Chemistry (ARC) strategy for the total synthesis of (−)-mandelalides A and L, the two most potent members of the mandelalide family. The design and implementation of a three-component

  扁桃腺苷包括一个结构复杂的海洋大环内酯类，该大环内酯类对几种人类癌细胞系显示出显着的细胞毒性。这里介绍了有关阴离子合成化学（ARC）策略发展的完整说明，该策略用于完全合成（-）-扁桃化物A和L（扁桃化物家族中两个最有力的成员）。三组分II型ARC /交叉偶联方案和四组分I ARC结合体的设计和实现可分别快速访问这些天然产物的关键四氢呋喃和四氢吡喃结构基序。合成的其他亮点包括烯丙基1,3-二醇的催化氧化环化，将北半球和南半球结合在一起的温和的Yamaguchi酯化反应以及后期的Heck大环化反应。50，1.3和3.1纳米，分别地）。这种合成方法还提供了几种高效非天然扁桃腺苷类似物的途径，包括生物素标记的扁桃腺苷探针，可用于未来的生物学研究。
• Total Synthesis of the Polyene-Polyol Macrolide RK-397, Featuring Cross-Couplings of Alkynylepoxide Modules
  作者：Svetlana A. Burova、Frank E. McDonald

  DOI：10.1021/ja039618+

  日期：2004.3.3

  from alkyne-epoxide couplings are converted into 1,3-diols by a sequence of hydroxyl-directed hydrosilylation, C-Si bond oxidation, and stereoselective ketone reduction with induction from the beta-hydroxyl group. The highly convergent nature of our synthetic pathway and the flexibility of the modular synthesis strategy for virtually any stereoisomer can provide access to other members of the polyene-polyol

  天然产物 RK-397 的全合成基于组装聚乙酸酯结构的新合成策略，通过亲核末端炔烃模块与在相反末端带有另一个炔烃的亲电环氧化物的有效交叉偶联。天然产物由四个主要模块构成：碳 3-9 的多烯前体和碳 10-16、17-22 和 23-33 的三个炔烃封端模块。每个模块都是在控制所有立体化学元素的情况下制备的，从炔烃-环氧化物偶联获得的炔醇通过一系列羟基导向的氢化硅烷化、C-Si 键氧化和立体选择性酮还原反应转化为 1,3-二醇来自β-羟基。
• A Short Total Synthesis of (+)-Cryptocarya Diacetate
  作者：Mukund K. Gurjar、Neelarapu Raghupathi、Mukund S. Chorghade

  DOI：10.3987/com-08-s(f)107

  日期：——

  A short synthesis of (+)-cryptocarya diacetate was achieved by employing three component linchpin coupling, diastereoselective reduction of β-hydroxyketone, and Z-selective HWE reaction as key transformations.

  通过采用三组分关键偶联、β-羟基酮的非对映选择性还原和 Z-选择性 HWE 反应作为关键转化，实现了 (+)-二乙酸隐核糖酯的短合成。