non-3-ynyl-benzene | 155725-39-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: non-3-ynyl-benzene
• 英文别名: non-3-yn-1-ylbenzene；Non-3-ynylbenzene
• CAS: 155725-39-6
• 化学式: C₁₅H₂₀
• 分子量: 200.324
• InChiKey: BAFUGNZHGZDXMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  [(E)-3-(benzenesulfinyl)-1-phenylnon-3-en-4-yl] diethyl phosphate 以81%的产率得到
  参考文献：
  名称：

  Satoh Tsuyoshi, Itoh Norifumi, Watanabe Shizue, Matsuno Haruko, Yamakawa +, Chem. lett, (1994) N 3, S 576-570

  摘要：

  DOI：

文献信息

• Ligand Exchange Reaction of Sulfoxides in Organic Synthesis. A Novel Method for Synthesizing Acetylenes from Carbonyl Compounds through β-Trifluoromethanesulfonyloxy Vinyl Sulfoxides
  作者：Tsuyoshi Satoh、Norifumi Itoh、Shizue Watanabe、Haruko Matsuno、Koji Yamakawa

  DOI：10.1246/cl.1994.567

  日期：1994.3

  α-Sulfinyl ketones were prepared by the reaction of alkyl phenyl sulfoxide or chloromethyl p-tolyl sulfoxide with aldehydes or methyl esters in high yields, and were converted to acetylenes through β-trifluoromethanesulfonyloxy vinyl sulfoxides by the ligand exchange reaction of the sulfinyl group.

  α-亚磺酰基酮是由烷基苯亚砜或氯甲基对甲苯基亚砜与醛或甲酯以高收率反应制备的，并通过亚磺酰基的配体交换反应通过β-三氟甲磺酰氧基乙烯基亚砜转化为乙炔。
• Palladium-Catalyzed Aerobic Oxidative Cross-Coupling Reactions of Terminal Alkynes with Alkylzinc Reagents
  作者：Mao Chen、Xiaolong Zheng、Wenqing Li、Jun He、Aiwen Lei

  DOI：10.1021/ja100630p

  日期：2010.3.31

  With air as the oxidant, terminal alkynes can be directly cross-coupled with alkylzinc reagents in the presence of a Pd catalyst at room temperature. CO was found to be critical in gaining high chemical yields and selectivities. A wide range of alkynes and alkylzinc reagents were tested, and good to excellent yields were obtained.

  以空气为氧化剂，在室温下，在钯催化剂的存在下，末端炔烃可以与烷基锌试剂直接交叉偶联。发现 CO 对于获得高化学产率和选择性至关重要。测试了范围广泛的炔烃和烷基锌试剂，并获得了良好的收率。
• Palladium-Catalyzed R(sp³)-Zn/R(sp)-SnBu₃ Oxidative Cross-Coupling
  作者：Aiwen Lei、Liqun Jin、Yingsheng Zhao、Haibo Wang

  DOI：10.1055/s-2007-990863

  日期：2008.2

  A novel bond formation through oxidative cross-coupling with desyl chloride as the oxidant has been investigated. The coupling can be carried out under mild conditions. The Csp3-center carbon was involved even in the presence of a β-H, and up to 90% of the desired cross-coupling product was obtained with the secondary Csp3-center substrate.

  研究了一种通过氧化交叉耦合形成新键的反应，其中使用了氯化苄作为氧化剂。该耦合可以在温和的条件下进行。即使在存在 β-H 的情况下，Csp3 中心碳仍然参与反应，并且在二级 Csp3 中心底物中获得了高达 90% 的所需交叉耦合产物。
• Broadly Applicable Ion Pair-Assisted Nucleophilic Substitution of sp³-Carbon Electrophiles with Alkynyltrifluoroborates
  作者：Shiwen Liu、Cláudio F. Tormena、Gerald B. Hammond、Bo Xu

  DOI：10.1021/acs.orglett.2c02507

  日期：2022.9.2

  smoothly with a wide range of sp3-carbon electrophiles, including propargyl methanesulfonates and unactivated alkyl triflates, to give Sonogashira-type products, via a novel ion pair-assisted nucleophilic substitution mechanism. An ion pair–organic complex, investigated using computational chemistry and in situ NMR experiments, may play a crucial role in this reaction.

  炔基三氟硼酸盐亲核试剂通过新的离子对辅助亲核取代机制与多种sp 3 -碳亲电子试剂（包括甲磺酸炔丙酯和未活化的三氟甲磺酸烷基酯）顺利反应，生成 Sonogashira 型产物。使用计算化学和原位核磁共振实验研究的离子对-有机复合物可能在该反应中发挥关键作用。
• Oxidative Cross-Coupling through Double Transmetallation:  Surprisingly High Selectivity for Palladium-Catalyzed Cross-Coupling of Alkylzinc and Alkynylstannanes
  作者：Yingsheng Zhao、Haibo Wang、Xiaohui Hou、Yanhe Hu、Aiwen Lei、Heng Zhang、Lizheng Zhu

  DOI：10.1021/ja0647351

  日期：2006.11.1

  Two different organometallic reagents now can cross-couple together with the oxidative cross-coupling strategy. Palladium catalyzed oxidative cross-couplings of alkylzinc and alkynylstannane reagents using desyl chloride as the oxidant have been explored, which produce the desired Csp-Csp3 cross-coupling product in surprisingly high selectivity and yields. The current catalytic system tolerates the presence of beta-H, and the reactions using long chain alkyl zinc reagents gave the cross-coupling product in excellent yields and selectivities.