1-phenyloct-3-en-1-yne | 132699-39-9

• 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: 1-phenyloct-3-en-1-yne
• 英文别名: oct-3-en-1-yn-1-ylbenzene；Oct-3-en-1-ynylbenzene；oct-3-en-1-ynylbenzene
• CAS: 132699-39-9
• 化学式: C₁₄H₁₆
• 分子量: 184.281
• InChiKey: HRFXQHRMNNWCOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-phenyloct-3-en-1-yne 在 (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate 、 Oxone 、 乙二胺四乙酸 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二甲醇缩甲醛 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 (2S,3R)-2-butyl-3-(2-phenylethynyl)oxirane 、 (2R,3S)-2-butyl-3-(2-phenylethynyl)oxirane
  参考文献：
  名称：

  二乙酸酮催化的烯烃不对称环氧化反应

  摘要：

  果糖衍生的二乙酸酮已被证明是不对称环氧化的有效催化剂。各种反式和三取代烯烃（包括缺电子 α,β-不饱和酯以及某些顺式烯烃）都获得了高 ee 值。

  DOI：

  10.1021/jo900330n
• 作为产物：
  描述：

  1-phenyloct-1-yn-3-yl acetate 在 indium(III) chloride 、 乙醇 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以36%的产率得到1-phenyloct-3-en-1-yne
  参考文献：
  名称：

  Nucleophilic Substitution of Secondary Alkyl-Substituted Propargyl Acetates: An Economic and Practical Indium Trichloride Catalyzed Access

  摘要：

  描述了一种经济实用的转化，将二级烷基取代的丙炔醇乙酸酯转化为多种亲核取代产物。该反应由廉价的氯化铟(InCl3)催化，获得了高产率和卓越的化学选择性。五元、六元和七元的丙炔环醚也通过该方法成功合成。

  DOI：

  10.1055/s-0030-1259557

文献信息

• A facile approach to spirocyclic butenolides through cascade cyclization/oxidative cleavage reactions of (Z)-enynols catalyzed by gold under dioxygen atmosphere
  作者：Feijie Song、Yuanhong Liu

  DOI：10.1016/j.jorganchem.2008.10.046

  日期：2009.2

  A facile approach for the syntheses of spirocyclic butenolides through cascade cyclization/oxidative cleavage reactions of (Z)-enynols bearing cyclic substituents at the C-1 position catalyzed by gold under dioxygen atmosphere has been developed. A variety of substituted butenolides was constructed in a regioselective manner from suitably substituted (Z)-2-en-4-yn-1-ols. (Z)-Enynols substituted both

  已经开发了一种在双氧气氛下通过金催化的在C-1位带有环状取代基的（Z）-烯醇的级联环化/氧化裂解反应合成螺环丁烯内酯的简便方法。从区域适当地取代的（Z）-2-en-4-yn-1-ols以区域选择性的方式构建了各种取代的丁烯内酯。在C2和C3位置均被取代的（Z）-烯醇提供中等至良好产率的螺环丁烯内酯，C-2未取代的（Z）-烯醇提供中等产率的产物，C-3未取代的（Z）-烯醇以低收率提供了所需的产物。
• Simple and efficient nickel-catalyzed cross-coupling reaction of alkenylalanes with alkynyl halides for synthesis of conjugated enynes
  作者：Hong-Liu Xiao、Gang Zhang、Rui-Qiang Luo、Qing-Han Li

  DOI：10.1016/j.tet.2021.132549

  日期：2022.1

  A NiCl2(PPh3)2/XantPhos catalyzed synthesis of conjugated enynes by the cross-coupling of terminal alkynyl halides with alkenylaluminum reagents at room temperature in DME solvent was developed under mild reaction conditions. The aryls bearing electron-donating or electron-withdrawing groups in alkynylhalides give the corresponding cross-coupling products conjugated enynes in good to excellent isolated

  NiCl 2 (PPh 3 ) 2 /XantPhos 通过末端炔基卤化物与链烯基铝试剂在室温下在温和的反应条件下在 DME 溶剂中的交叉偶联来催化合成共轭烯炔。炔基卤化物中带有给电子或吸电子基团的芳基产生相应的交叉偶联产物共轭烯炔，分离产率高达 97%。该过程简单易行，为合成共轭烯炔衍生物提供了一种有效的方法。根据实验结果，提出了一种可能的催化循环。
• A new method for the construction of the pyrrole ring by the carbonylcobalt-catalyzed reaction of trimethylsilyl cyanide with acetylenes. Its scope and limitations
  作者：Naoto Chatani、Terukiyo Hanafusa

  DOI：10.1021/jo00006a038

  日期：1991.3

  The carbonylcobalt-catalyzed reaction of acetylenes with trimethylsilyl cyanide (1) to give 5-amino-1H-pyrrole-2-carbonitriles is described. Reaction of the symmetric internal acetylenes, 4-octyne (2a) and 2,9-dimethyl-5-decyne (2b), with 1 in the presence of a cobalt complex gave 3a and 3b, respectively, in high yield. From unsymmetric acetylenes were obtained mixtures of regioisomeric pyrroles. The regioisomeric ratio depended on the substitution pattern of the acetylenes and on the kind of substituents possessed by the acetylenes. In the case of the internal unsymmetric acetylenes, 2c-2f, isomers in which the bulkier of the two substituents appeared at the 4-position of the pyrrole ring were obtained as the main products. However, the reaction of internal acetylenes bearing an ester group (2g and 2h) gave a reversed selectively. In case of the terminal acetylenes, 1-octyne (2k), 21, and 2m, isomers in which the alkyl group was located at the 3-position of the pyrrole ring were obtained highly selectively. A new cobalt complex (8), prepared by the reaction of CO2(CO)8 with excess 1, catalyzed the formation of pyrrole 3a from 2a and 1. The stoichiometric reaction of complex 8 with 2a also gave 3a in a good yield.
• A Diacetate Ketone-Catalyzed Asymmetric Epoxidation of Olefins
  作者：Bin Wang、Xin-Yan Wu、O. Andrea Wong、Brian Nettles、Mei-Xin Zhao、Dajun Chen、Yian Shi

  DOI：10.1021/jo900330n

  日期：2009.5.15

  A fructose-derived diacetate ketone has been shown to be an effective catalyst for asymmetric epoxidation. High ee values have been obtained for a variety of trans and trisubstituted olefins including electron-deficient α,β-unsaturated esters as well as certain cis olefins.

  果糖衍生的二乙酸酮已被证明是不对称环氧化的有效催化剂。各种反式和三取代烯烃（包括缺电子 α,β-不饱和酯以及某些顺式烯烃）都获得了高 ee 值。
• Nucleophilic Substitution of Secondary Alkyl-Substituted Propargyl Acetates: An Economic and Practical Indium Trichloride Catalyzed Access
  作者：Zhuang-ping Zhan、Min Lin、Lu Hao、Xiao-tao Liu、Qing-zhen Chen、Feng Wu、Ping Yan、Su-xia Xu、Xin-liang Chen、Jia-jie Wen

  DOI：10.1055/s-0030-1259557

  日期：2011.3

  An economic and practical transformation from secondary alkyl-substituted propargyl acetates to a variety of nucleophilic substitution products was described. This reaction was catalyzed by inexpensive InCl3. High yields and excellent chemoselectivity were obtained. The five-, six-, and seven-membered propargyl cyclo­ethers were also successfully constructed by this protocol.

  描述了一种经济实用的转化，将二级烷基取代的丙炔醇乙酸酯转化为多种亲核取代产物。该反应由廉价的氯化铟(InCl3)催化，获得了高产率和卓越的化学选择性。五元、六元和七元的丙炔环醚也通过该方法成功合成。