6-phenyl-hex-5-ynoic acid ethyl ester | 126761-10-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 6-phenyl-hex-5-ynoic acid ethyl ester
• 英文别名: ethyl 6-phenylhex-5-ynoate
• CAS: 126761-10-2
• 化学式: C₁₄H₁₆O₂
• 分子量: 216.28
• InChiKey: ADFDKOKLIWUJBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-phenyl-hex-5-ynoic acid ethyl ester 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以79%的产率得到(6-iodohex-1-yn-1-yl)benzene
  参考文献：
  名称：

  高度官能化的铜锌试剂RCu（CN）ZnI对1-卤代炔烃和炔属酯的反应性

  摘要：

  高度官能化的有机金属化合物RCu（CN）ZnI 1与1-卤代炔烃有效反应，从而以高收率提供多官能团炔烃。该方法已被用于分3步制备Amathes c-igigrum的信息素，总产率为64％。试剂1还在过量的Me 3 SiCl存在下添加至炔属酯中，以提供多官能化的C-甲硅烷基化的烯属酯。在丙酸乙酯的情况下，该反应是高度立体选择性的，并提供97％纯的（E）-2-三甲基甲硅烷基乙烯酯。

  DOI：

  10.1016/s0040-4039(01)80511-6
• 作为产物：
  描述：

  苯基乙炔三丁基锡 、 bromo(4-ethoxy-4-oxobutyl)zinc 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 2-氯-2-苯基苯乙酮 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以92%的产率得到6-phenyl-hex-5-ynoic acid ethyl ester
  参考文献：
  名称：

  Oxidative Cross-Coupling through Double Transmetallation:  Surprisingly High Selectivity for Palladium-Catalyzed Cross-Coupling of Alkylzinc and Alkynylstannanes

  摘要：

  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.

  DOI：

  10.1021/ja0647351

文献信息

• 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。
• The reactivity of the highly functionalized copper, zinc reagents RCu(CN)ZnI toward 1-haloalkynes and acetylenic esters
  作者：Ming Chang P. Yeh、Paul Knochel

  DOI：10.1016/s0040-4039(01)80511-6

  日期：1989.1

  The highly functionalized organometallics RCu(CN)ZnI 1 react efficiently with 1-haloalkynes providing polyfunctionalized alkynes in high yields. This method has been used to prepare a pheromone of the Amathes c-nigrum in 3 steps and 64% overall yield. The reagents 1 also add in the presence of an excess of Me3SiCl to acetylenic esters to afford polyfunctionalized C—silylated ethylenic esters. In the

  高度官能化的有机金属化合物RCu（CN）ZnI 1与1-卤代炔烃有效反应，从而以高收率提供多官能团炔烃。该方法已被用于分3步制备Amathes c-igigrum的信息素，总产率为64％。试剂1还在过量的Me 3 SiCl存在下添加至炔属酯中，以提供多官能化的C-甲硅烷基化的烯属酯。在丙酸乙酯的情况下，该反应是高度立体选择性的，并提供97％纯的（E）-2-三甲基甲硅烷基乙烯酯。
• 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.