O-(pent-4-yn-1-yl)hydroxylamine | 149649-83-2

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: O-(pent-4-yn-1-yl)hydroxylamine
• 英文别名: O-(pent-4-yn-1-yl) hydroxylamine hydrochloride；O-pent-4-ynylhydroxylamine
• CAS: 149649-83-2
• 化学式: C₅H₉NO
• 分子量: 99.1326
• InChiKey: JAFCRLMYPPBVMU-UHFFFAOYSA-N

物化性质

• 沸点：
  185.5±23.0 °C(Predicted)
• 密度：
  0.945±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(pent-4-yn-1-yl)hydroxylamine 在 selenium(IV) oxide 、 silver hexafluoroantimonate 、 carbonyl(η-5-cyclopentadienyl)diiodocobalt(III) 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 、 cesium pivalate 、 三甲基乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 2,2,2-三氟乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 60.0h， 生成 2,3-dihydropyrrolo[1,2-b]isoquinoline-1,5-dione
  参考文献：
  名称：

  一种通用的Cp * CoIII催化的分子内C-H活化方法，可有效地合成香霉素，原小T碱和触毛生物碱

  摘要：

  在此，我们报告Cp * Co III催化的C H活化方法是创建高度有价值的异喹诺酮和吡啶酮的重要步骤，这些异喹啉酮和吡啶酮可以轻松地用于各种芳香族素，原小ber碱和tylophora生物碱的总合成。这种特殊的CH活化/环化反应是通过多个末端以及内部炔烃偶联伙伴实现的，具有广泛的应用范围和出色的官能团耐受性。本文报道的该方案的合成适用性已在两个Topo-I-抑制剂和两个8-氧代小ber碱核心的合成中得到了证明，这些核心可进一步制成四氢小ber碱和原小ber碱生物碱。此外，这些构件也以方便的方式转化为六种不同的tylophora生物碱。

  DOI：

  10.1002/chem.201702648
• 作为产物：
  描述：

  4-戊炔-1-醇 在 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 O-(pent-4-yn-1-yl)hydroxylamine
  参考文献：
  名称：

  铑（III）催化的环丁烯的C（sp2）-H功能化。获得环[c]吡啶酮和-吡啶。

  摘要：

  衍生自环丁烯基羧酸的O-（ω-炔基）异羟肟酸酯被认为是分子内铑（III）催化的杂环化反应的可行底物，后者导致了不同取代的环丁环[c]吡啶酮。在四元环的电环开环之后，所得环丁吡啶酮的进一步官能化使得能够合成环丁[c]吡啶和其他氮杂环。

  DOI：

  10.1021/acs.orglett.9b03139

文献信息

• Asymmetric Synthesis of Polyhydroxylated <i>N</i>-Alkoxypiperidines by Ring-Closing Double Reductive Amination: Facile Preparation of Isofagomine and Analogues
  作者：Gaëlle Malik、Xavier Guinchard、David Crich

  DOI：10.1021/ol203213f

  日期：2012.1.20

  A de novo synthesis of novel polyhydroxylated N-alkoxypiperidines based on the ring-closing double reductive amination of 1,5-dialdehydes, obtained by oxidative cleavage of cyclopentene derivatives, with O-substituted hydroxylamines is reported. Isofagomine was accessed by cleavage of the N–O bond of an N-alkoxypiperidine.

  报道了一种新的多羟基化的N-烷氧基哌啶的从头合成，该合成是基于通过用O-取代的羟胺对环戊烯衍生物进行氧化裂解而得到的1，5-二醛的双环还原胺化。通过切割N-烷氧基哌啶的N-O键可访问异黄花碱。
• 10.3390/molecules29122942
  作者：Moianos, Dimitrios、Makri, Maria、Prifti, Georgia-Myrto、Chiotellis, Aristeidis、Pappas, Alexandros、Woodson, Molly E.、Tajwar, Razia、Tavis, John E.、Zoidis, Grigoris

  DOI：10.3390/molecules29122942

  日期：——

  (HPD) imines that effectively inhibit the HBV RNase H. In our effort to further explore the HPD scaffold, we designed, synthesized, and evaluated 18 novel HPD oximes, as well as 4 structurally related minoxidil derivatives and 2 barbituric acid counterparts. The new analogs were docked on the RNase H active site and all proved able to coordinate the two Mg2+ ions in the catalytic site. All of the new HPDs

  乙型肝炎病毒 （HBV） 仍然是一个全球性的健康威胁。核糖核酸酶 H （RNase H） 是病毒聚合酶蛋白的一部分，在病毒基因组复制过程中切割 pgRNA 模板。抑制 RNase H 活性会阻止 （+） DNA 链合成，并导致非功能性基因组的积累，从而终止病毒复制周期。RNase H 虽然前景广阔，但仍然是针对 HBV 的药物靶点未被充分探索。我们之前报道了一系列有效抑制 HBV RNase H 的 N-羟基吡啶二酮 （HPD） 亚胺的鉴定。在我们进一步探索 HPD 支架的努力中，我们设计、合成和评估了 18 种新型 HPD 肟，以及 4 种结构相关的米诺地尔衍生物和 2 种巴比妥酸对应物。新的类似物对接在 RNase H 活性位点上，并且都被证明能够协调催化位点中的两个 Mg2 + 离子。所有新的 HPD 都有效抑制了细胞检测中的病毒复制，EC50 值在低 μM 范围 （1.1–7.7 μM）
• Synthesis and Pharmacological Characterization of <i>O</i>-Alkynyloximes of Tropinone and <i>N</i>-Methylpiperidinone as Muscarinic Agonists
  作者：Rong Xu、Meng-Kwoon Sim、Mei-Lin Go

  DOI：10.1021/jm9708588

  日期：1998.8.1

  A number of O-alkynyloximes of tropinone and N-methyl-4-piperidinone have been synthesized and evaluated for muscarinic activity. The affinities of these oximes were tested in homogenates of cerebral cortex, heart, and submandibulary glands from rats using [H-3]pirenzepine and [H-3]- N-methylscopolamine as radioligands. The oximes bind to the cortical muscarinic receptors with pK(i) values varying from 3 to 7. Higher binding affinities were observed for the O-alkynyl tropinone oximes than the corresponding piperidinone analogues. Binding to the muscarinic sites in the heart and submandibulary glands was also observed but with lower affinities. Good M-1 subtype selectivity (10-fold or greater) was observed with some oximes (26a, 28a, 32a) at the cortical sites. These oximes also attenuated scopolamine-induced impairment of the water mask task in mice. Functional assays for Ma activity on the rat aorta showed that all oximes possessed M-3 agonist action but M-2 agonist activity was not observed at the endothelium-denuded rabbit aorta. Analysis of the quantitative structure-activity relationship (QSAR) indicated that the Connolly surface area is an important determinant of activity, accounting for 70% of the variation in cortical binding affinity among the oximes.
• Stereocontrolled Synthesis of a Complex Library via Elaboration of Angular Epoxyquinol Scaffolds
  作者：Xiaoguang Lei、Nava Zaarur、Michael Y. Sherman、John A. Porco

  DOI：10.1021/jo050956y

  日期：2005.8.1

  We have accomplished the synthesis of a complex chemical library via elaboration of angular epoxyquinol scaffolds with distinct skeletal frameworks. The key strategy involves highly stereocontrolled [4 + 2] Diels-Alder cycloadditions of chiral, nonracemic epoxyquinol dienes to generate the scaffolds. Further scaffold diversification involves hydrogenation, epimerization, dehydration, and condensation of the carbonyl group with alkoxyamine and carbazate building blocks. Further elaboration of the scaffolds also provided new skeletal frameworks using hydroxyl-directed Diels-Alder cycloaddition and reductive N-N bond cleavage. The overall process afforded 244 highly complex and functionalized compounds. Preliminary biological screening of the library uncovered six compounds which showed significant inhibition of Hsp 72 induction.
• A General Cp*Co^III-Catalyzed Intramolecular C−H Activation Approach for the Efficient Total Syntheses of Aromathecin, Protoberberine, and Tylophora Alkaloids
  作者：Andreas Lerchen、Tobias Knecht、Maximilian Koy、Constantin G. Daniliuc、Frank Glorius

  DOI：10.1002/chem.201702648

  日期：2017.9.7

  Herein, we report a Cp*CoIII‐catalyzed C−H activation approach as the key step to create highly valuable isoquinolones and pyridones as building blocks that can readily be applied in the total syntheses of a variety of aromathecin, protoberberine, and tylophora alkaloids. This particular C−H activation/annulation reaction was achieved with several terminal as well as internal alkyne coupling partners

  在此，我们报告Cp * Co III催化的C H活化方法是创建高度有价值的异喹诺酮和吡啶酮的重要步骤，这些异喹啉酮和吡啶酮可以轻松地用于各种芳香族素，原小ber碱和tylophora生物碱的总合成。这种特殊的CH活化/环化反应是通过多个末端以及内部炔烃偶联伙伴实现的，具有广泛的应用范围和出色的官能团耐受性。本文报道的该方案的合成适用性已在两个Topo-I-抑制剂和两个8-氧代小ber碱核心的合成中得到了证明，这些核心可进一步制成四氢小ber碱和原小ber碱生物碱。此外，这些构件也以方便的方式转化为六种不同的tylophora生物碱。