辛-5-烯-4-酮 | 30647-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 辛-5-烯-4-酮
• 英文名称: (E)-oct-5-en-4-one
• CAS: 30647-85-9
• 化学式: C₈H₁₄O
• 分子量: 126.199
• InChiKey: SEVSRVAJBFYTEX-FNORWQNLSA-N

物化性质

• 沸点：
  180.4±9.0 °C(Predicted)
• 密度：
  0.833±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  辛-5-烯-4-酮 在 zinc(II) tetrahydroborate 、 C₂₀H₂₅N₃O*2C₁₃H₁₇NO₄ 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 、 甲苯 为溶剂， 反应 189.33h， 生成 methyl S-((3R,5S)-5-hydroxyoctan-3-yl)-L-cysteinate
  参考文献：
  名称：

  通过催化剂控制的半胱氨酸衍生物的1,4-加成合成Thelepamide和Thelepamide的结构修改

  摘要：

  据报道，首次从海洋蠕虫Thelepus crispus获得了具有细胞毒性的四酮化合物-氨基酸-（-）-thelepamide的对映选择性全合成和结构重新分配。收敛方法可从四个简单的构建基元中以六个步骤访问所有的lepamide非对映异构体。合成的关键特征包括应用Melchiorre的有机催化thia-Michael反应和超声辅助的N，O-乙缩醛-半缩醛部分的组装。通过NMR-DFT分析确认了校正后的结构。

  DOI：

  10.1021/acs.orglett.7b03706
• 作为产物：
  描述：

  反-4-辛烯 在 N-羟基邻苯二甲酰亚胺 、 sodium perchlorate 作用下， 以 吡啶 、 乙腈 为溶剂， 以36%的产率得到辛-5-烯-4-酮
  参考文献：
  名称：

  Masui, Masaichiro; Hosomi, Katsuko; Tsuchida, Keiichi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 11, p. 4798 - 4802

  摘要：

  DOI：

文献信息

• 5—Endo ring closures of allylic hydroperoxides: Useful routes to 1,2—dioxolanes involving strongly stereoselective free radical and polar reactions
  作者：John L. Courtneidge、Melanie Bush、Lay See Loh

  DOI：10.1016/s0040-4020(01)92274-4

  日期：1992.1

  Intramolecular cyclisation of simple allylic hydroperoxides to give substituted 1,2—dioxolanes using electrophilic reagents has been investigated. Closure using mercury(II) acetate and electrophilic halogen reagents (NBS, Br2 ButOC1) occurs by Markovnikov—directed and conformationally strict stereospecificity. Subsequent free— radical reaction of the mercurated dioxolanes involved specific reaction

  已经研究了使用亲电子试剂将简单的烯丙基氢过氧化物分子内环化以生成取代的1,2-二氧戊环的方法。使用乙酸汞（II）和亲电卤素试剂（NBS，Br 2 Bu t OC1）封闭是由马尔科夫尼科夫（Markovnikov）指导的，构象严格的立体特异性。随后，汞化二氧戊环的自由基反应涉及特定的反应，该反应涉及来自中间体二氧戊环基自由基的空间未保护面的反应。
• Thelepamide: An Unprecedented Ketide-Amino Acid from <i>Thelepus crispus</i>, a Marine Annelid Worm
  作者：Jaime Rodríguez、Rosa M. Nieto、María Blanco、Frederick A. Valeriote、Carlos Jiménez、Phillip Crews

  DOI：10.1021/ol403350e

  日期：2014.1.17

  Thelepamide (1) was characterized during a program to study cytotoxic substances from an unusual source, the tidal zone-derived annelid Thelephus crispus. Its structure contains a tetraketide and a tripeptide subunit and possesses striking atom diversity, consisting of 17 carbons and 8 heteroatoms. The relative configurations at four chiral sites were elucidated via ROESY, J-based configurational analysis

  Thelepamide ( 1 ) 在一项研究来自一种不寻常来源的细胞毒性物质的计划中被表征，潮带来源的环节动物Thelephus creamus。它的结构包含一个四酮和一个三肽亚基，并具有惊人的原子多样性，由 17 个碳和 8 个杂原子组成。通过 ROESY、基于J的构型分析和 DFT 计算阐明了四个手性位点的相对构型。它对白血病细胞有适度的活性 (IC 50 = 5 μg/mL)，对实体瘤细胞系无活性。
• HCV PROTEASE INHIBITORS AND USES THEREOF
  申请人：Celgene Avilomics Research, Inc.

  公开号：US20150031106A1

  公开（公告）日：2015-01-29

  The present invention provides compounds, pharmaceutically acceptable compositions thereof, and methods of using the same.

  本发明提供了化合物、药学上可接受的组合物以及使用它们的方法。
• Natural preservatives and antimicrobial agents, including compositions thereof
  申请人：Unigen, Inc.

  公开号：US10780173B2

  公开（公告）日：2020-09-22

  Compositions are disclosed herein that comprise a mixture of at least one Albizia extract and a Magnolia extract. In some embodiments, the composition comprises a mixture of at least one Albizia extract enriched for one or more macrocyclic alkaloids and at least one Magnolia extract enrich for one or more lignans.

  本文公开的组合物包括至少一种白花蛇舌草提取物和一种厚朴提取物的混合物。在某些实施方案中，组合物包括至少一种富含一种或多种大环生物碱的白花蛇舌草提取物和至少一种富含一种或多种木脂素的厚朴提取物的混合物。
• Oxidation of Allenes and Alkynes with Hydrogen Peroxide Catalyzed by Cetylpyridinium Peroxotungstophosphate (PCWP)
  作者：Satoshi Sakaguchi、Seiji Watase、Yuji Katayama、Yasuyuki Sakata、Yutaka Nishiyama、Yasutaka Ishii

  DOI：10.1021/jo00098a028

  日期：1994.9

  The oxidation of allenes and alkynes with hydrogen peroxide catalyzed by peroxotungstophosphate (PCWP) was examined. A variety of allenes were first converted into the corresponding alpha-ethoxy ketones upon treatment with 35% H2O2 under the influence of PCWP in a mixed solvent consisting of ethanol and dichloromethane. When the reaction was carried out using tert-butyl alcohol as a solvent, approximately a 1:1 regioisomeric mixture of alpha-hydroxy ketones was obtained along with a small amount of alpha-tert-butoxy ketone. Oxidation of internal alkynes such as 4-octyne by the PCWP-H2O2 system under phase-transfer conditions using chloroform produced alpha,beta-epoxy ketones in good yields. The same reaction in a mixed solvent of ethanol and chloroform gave alpha,beta-unsaturated ketones rather than alpha,beta-epoxy ketones. Plausible reaction paths are proposed for the oxidation of allenes and alkynes by the PCWP-H2O2 system.