non-1-en-8-yn-5-one | 141738-84-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: non-1-en-8-yn-5-one
• CAS: 141738-84-3
• 化学式: C₉H₁₂O
• 分子量: 136.194
• InChiKey: WRYUENCZUGJJHO-UHFFFAOYSA-N

物化性质

• 沸点：
  209.3±15.0 °C(Predicted)
• 密度：
  0.889±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  non-1-en-8-yn-5-one 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 反应 6.5h， 以79%的产率得到4-oxooct-7-ynal
  参考文献：
  名称：

  In(OTf)₃-Catalyzed Cascade Cyclization for Construction of Oxatricyclic Compounds

  摘要：

  A highly diastereoselective cascade cyclization reaction has been developed for establishing a series of oxatricyclic compounds using Chan's diene and simple keto H alkynal substrates with only 1 mol % of In(OTf)(3) as the catalyst in 82-92% yields. The potential utility of this synthetic strategy has been demonstrated in model studies for the construction the core structures of 1 alpha,8 alpha:4 alpha,5 alpha-diepoxy-4,5-dihydroosmitopsin and cortistatin

  DOI：

  10.1021/acs.orglett.8b03461
• 作为产物：
  描述：

  4-pentyn-1-al 在 碘 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 magnesium 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 non-1-en-8-yn-5-one
  参考文献：
  名称：

  In(OTf)₃-Catalyzed Cascade Cyclization for Construction of Oxatricyclic Compounds

  摘要：

  A highly diastereoselective cascade cyclization reaction has been developed for establishing a series of oxatricyclic compounds using Chan's diene and simple keto H alkynal substrates with only 1 mol % of In(OTf)(3) as the catalyst in 82-92% yields. The potential utility of this synthetic strategy has been demonstrated in model studies for the construction the core structures of 1 alpha,8 alpha:4 alpha,5 alpha-diepoxy-4,5-dihydroosmitopsin and cortistatin

  DOI：

  10.1021/acs.orglett.8b03461

文献信息

• Regioselective Crossed Aldol Reactions under Mild Conditions via Synergistic Gold-Iron Catalysis
  作者：Teng Yuan、Xiaohan Ye、Pengyi Zhao、Shun Teng、Yaping Yi、Jin Wang、Chuan Shan、Lukasz Wojtas、Jonathan Jean、Hao Chen、Xiaodong Shi

  DOI：10.1016/j.chempr.2020.03.014

  日期：2020.6

  was identified as an essential co-catalyst in preventing vinyl Au protodeauration and facilitating nucleophilic additions. Effective C–C bond formation was achieved under mild conditions (room temperature) with excellent regioselectivity and high efficiency (1% [Au], up to 95% yields). The intramolecular reaction was also achieved, giving successful macrocyclization (16–31 ring sizes) with excellent

  开发了一种协同金铁 (Au-Fe) 催化系统，用于顺序炔烃水合和乙烯基 Au 加成至醛或酮。 Fe(acac) 3被认为是防止乙烯基 Au 原型脱气和促进亲核加成的重要助催化剂。在温和条件（室温）下实现了有效的 C-C 键形成，具有出色的区域选择性和高效率（1% [Au]，产率高达 95%）。还实现了分子内反应，成功进行了大环化（16-31 个环尺寸），且收率优异（高达 90%，克级），无需进一步稀释 (0.2 M)，这突显了这种新的交叉羟醛策略在挑战中的巨大潜力。目标分子合成。
• Alkyne Trifunctionalization via Divergent Gold Catalysis: Combining π-Acid Activation, Vinyl–Gold Addition, and Redox Catalysis
  作者：Teng Yuan、Qi Tang、Chuan Shan、Xiaohan Ye、Jin Wang、Pengyi Zhao、Lukasz Wojtas、Nicholas Hadler、Hao Chen、Xiaodong Shi

  DOI：10.1021/jacs.1c01811

  日期：2021.3.17

  Here we report the first example of alkyne trifunctionalization through simultaneous construction of C–C, C–O, and C–N bonds via gold catalysis. With the assistance of a γ-keto directing group, sequential gold-catalyzed alkyne hydration, vinyl–gold nucleophilic addition, and gold(III) reductive elimination were achieved in one pot. Diazonium salts were identified as both electrophiles (N source) and

  在这里，我们报告了第一个通过金催化同时构建 C-C、C-O 和 C-N 键进行炔烃三官能化的例子。在γ-酮基导向基团的帮助下，连续金催化炔烃水合、乙烯基-金亲核加成和金(III)还原消除在一锅中实现。重氮盐被鉴定为亲电子试剂（N源）和氧化剂（C源）。乙烯基-金（III）中间体被证明是重氮的有效亲核试剂，可高效促​​进亲核加成和还原消除。在温和条件（室温或 40 °C）下，实现了相当全面的反应序列，具有优异的产率（高达 95%）和广泛的范围（>50 示例）。
• Synthesis of γ- and δ-Lactones from Alkynols
  作者：Marcello Tiecco、Lorenzo Testaferri、Andrea Temperini、Raffaella Terlizzi、Luana Bagnoli、Francesca Marini、Claudio Santi

  DOI：10.1055/s-2006-932477

  日期：——

  The reaction of alkynyl phenyl selenides with p-toluene-sulfonic acid gives rise to a proton-induced ring-closure reaction affording γ- and 5-lactones.

  炔基苯基硒化物与对甲苯磺酸的反应引起质子诱导的闭环反应，得到 γ-和 5-内酯。
• 一种双吖丙啶基光交联探针中间体及衍生物的制备方法
  申请人：中国人民解放军海军军医大学

  公开号：CN114907197A

  公开（公告）日：2022-08-16

  本发明公开了一种双吖丙啶基光交联探针中间体及衍生物的制备方法，包括以下步骤： 将配体、过渡金属催化剂溶于溶剂中超声混匀，加入化合物III、化合物II、碱、光催化剂，在室温下充入氩气保护，光照反应，获得式I所示化合物；本发明提供的双吖丙啶基光交联探针中间体及衍生物的制备方法，主要以醛与卤化物为主要原料，原料具有刺激性小、易于获得的特点。本发明在常温常压下，利用光催化偶联反应，合成步骤简洁，显著提高合成产率，且反应后除产物外生成无机盐，对环境污染小，绿色环保。
• The TandemPauson-Khand Reaction
  作者：Marc Thommen、Andrei L. Veretenov、R�gine Guidetti-Grept、Reinhart Keese

  DOI：10.1002/hlca.19960790214

  日期：1996.3.20

  AbstractThe conditions for the novel tandem Pauson‐Khand reaction have been explored. The highly functionalized tetracyclic compounds 11c, 11d, and 16 were prepared from the ene‐diynes 4c, 4d, and 10 by treatment with 2 equiv. of [Co2(CO)8] and 4‐methylmorpholine N‐oxide (NMO) or Me3NO in yields of 24, 22, and 53%, respectively (Table). In the presence of 1–3 equiv. of H2O added to the NMO used for induction of the Pauson‐Khand reaction of 6d, a mixture of cyclopentanones 17/18 and cyclopentenones 12/13 was obtained (Scheme 5). The first example of a [Co2(CO)6]‐induced highly stereoselective ene reaction is described. To account for these results, the formation of intermediates are proposed (Schemes 6 and 7) which hitherto have not been considered in the mechanistic description of the Pauson‐Khand reaction.