1-苯基-2-辛烯 | 64275-34-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-苯基-2-辛烯
• 英文名称: 1-phenyl-2-octene
• 英文别名: oct-2-en-1-ylbenzene；1-phenyl-oct-2ξ-ene；1-Phenyl-oct-2ξ-en；Oct-2-enylbenzene
• CAS: 64275-34-9
• 化学式: C₁₄H₂₀
• 分子量: 188.313
• InChiKey: JRVGEBQVFIWWSO-UHFFFAOYSA-N

物化性质

• 沸点：
  135.8 °C(Press: 14 Torr)
• 密度：
  0.8704 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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-苯基-2-辛烯 、 丙二酸二乙酯 在 吗啉 、 (R)-1-[(S_P)-2-(dicyclohexylphosphino)ferrocenyl]ethyldi-tert-butylphosphine 、 bis(η3-allyl-μ-chloropalladium(II)) 、 四(3,5-二(三氟甲基)苯基)硼酸钠 作用下， 以59 %的产率得到diethyl (R,E)-2-(1-phenyloct-1-en-3-yl)malonate
  参考文献：
  名称：

  对映选择性钯催化远程二烯的定向迁移烯丙基化

  摘要：

  报道了通过钯催化的同时/定向链行走实现远程二烯的对映选择性迁移烯丙基化。该转化提供了实现多个连续 C(sp 3 )−H 键的立体选择性功能化的潜在途径。

  DOI：

  10.1002/anie.202307628
• 作为产物：
  描述：

  (E)-1-phenyl-1-octen-3-ol 在 吡啶 、 正丁基锂 、 (1,1'-双(二苯基膦)二茂铁)二氯化镍 、 (E)-hept-1-en-1-yl-1,3,2-benzodioxaborole 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 生成 1-苯基-2-辛烯
  参考文献：
  名称：

  Nickel-Catalyzed Coupling Reaction of 1,3-Disubstituted Secondary Allylic Carbonates and Lithium Aryl- and Alkenylborates

  摘要：

  This account describes coupling reaction of 1,3-disubstituted secondary allylic carbonates with lithium aryl- and alkenylborates in the presence of a nickel. catalyst. Berates examined are 4, 5, and 6, and reactivity and selectivity were investigated using the allylic carbonates la and Ib. Coupling of la,b with berates 4 was effected with the nickel catalyst, NiCl2(PPh(3))(2) or NiCl2(dppf), in THF at 45-65 degrees C to provide products 3 in good yields with almost 100% regio- and stereoselectivities. Trivalent organoboranes prepared from acetylenes by hydroboration with catecholborane also underwent coupling reaction with la,b after transformation to berates 5 with MeLi. Though coupling using 4 and 5 required elevated temperature (45-65 degrees C), cyclic berates 6 prepared in situ from boronates 8 and MeLi were found to couple with la,b at room temperature or below. Regio- and stereoselectivities were almost 100% as were observed in the cases of 4 and 5. In these reactions, palladium complexes such as Pd(PPh(3))(4), Pd-2(dba)(3) . CHCl3 + 2 PPh(3) showed no catalytic activity. Stereochemical aspect of the present reaction was studied using cyclohexenyl carbonate 24 with 2-furylborate 4e and phenylborate 6a, and was found to proceed with overall anti fashion. With additional experiments, the mechanism of the present reaction was discussed in terms of transient pi-allylnickel intermediates.

  DOI：

  10.1021/jo960458c

文献信息

• Selective formation of non-conjugated olefins by samarium(II)-mediated elimination/isomerization of allylic benzoates
  作者：Sara L. Schaefer、Connor L. Roberts、Erasmus O. Volz、Monika R. Grasso、Gregory W. O’Neil

  DOI：10.1016/j.tetlet.2013.08.136

  日期：2013.11

  Aromatic allylic benzoates can be selectively transformed to the corresponding benzoate eliminated olefin by the action of samarium diiodide. Depending on the substrate and the elimination conditions, high selectivity for the non-conjugated alkene product can be achieved.

  可以通过二碘化ates的作用将芳族烯丙基苯甲酸酯选择性地转化为相应的苯甲酸酯消除的烯烃。取决于底物和消除条件，可以实现对非共轭烯烃产物的高选择性。
• Copper-catalyzed asymmetric allylic substitution with aryl and ethyl Grignard reagents
  作者：Khalid B. Selim、Ken-ichi Yamada、Kiyoshi Tomioka

  DOI：10.1039/b809140d

  日期：——

  Phenyl- and ethyl-magnesium bromides undergo regioselective asymmetric allylic substitution with high enantioselectivity under the catalysis of chiral amidophosphane-copper(I) complexes.

  苯基和乙基镁溴化物在手性酰胺基膦-铜（I）配合物的催化下，具有对映选择性高的区域选择性不对称烯丙基取代。
• Sodium tetraphenylborate as a phenylating reagent in the palladium-catalyzed phenylation of alkenes and acid chlorides
  作者：Chan Sik Cho、Koichi Itotani、Sakae Uemura

  DOI：10.1016/0022-328x(93)80305-u

  日期：1993.1

  (NaBPh4) reacts with terminal alkenes in acetic acid at 25°C in the presence of a catalytic amount of palladium(II) acetate together with silver acetate as a re-oxidant to give the corresponding phenylated alkenes in 22–87% yield. It also reacts with acid chlorides in tetrahydrofuran (THF) at 25°C in the presence of a catalytic amount of tetrakis(triphenylphosphine)palladium(0) to give the corresponding

  四苯硼酸钠（NaBPh 4）在催化量的乙酸钯（II）和乙酸银作为再氧化剂的存在下，于25°C在乙酸中与末端烯烃反应，得到22-87％的相应苯基化烯烃屈服。在催化量的四（三苯基膦）钯（0）​​存在下，它还会与酰氯在四氢呋喃（THF）中在25°C下反应，以51-100％的收率得到相应的苯基酮。在乙酸钯（II）或氯钯酸钠（Na 2 PdCl 4）存在下，于25°C在甲醇中用1–30 atm一氧化碳（CO）进行硼酸盐的羰基化反应会产生较低的二苯甲酮收率（9–30％）和苯甲酸甲酯，较高的压力有利于后者的形成。
• Zirconium-mediated conversion of homoallylic ethers into cyclopropane derivatives
  作者：Vincent Gandon、Christophe Laroche、Jan Szymoniak

  DOI：10.1016/s0040-4039(03)01125-0

  日期：2003.6

  Homoallylic ethers react with Cp2ZrCl2/2 n-BuLi reagent to afford cyclopropane derivatives. Cyclopropylcarbinyl–homoallyl rearrangements involving zirconium species are observed depending on the substrate structure.

  高烯丙基醚与反应的Cp 2的ZrCl 2 /2 Ñ正丁基锂试剂，得到环丙烷衍生物。根据底物结构，观察到涉及锆物种的环丙基羰基-高烯丙基重排。
• Synthesis of Farnesol Analogues through Cu(I)-Mediated Displacements of Allylic THP Ethers by Grignard Reagents
  作者：Mark F. Mechelke、David F. Wiemer

  DOI：10.1021/jo990161p

  日期：1999.6.1

  The synthesis of a family of farnesol analogues, incorporating aromatic rings, has been achieved in high yields through the development of a regioselective coupling of allylic tetrahydropyranyl ethers with organometallic reagents. The allylic THP group is displaced readily by Grignard reagents in the presence of Cu(I) halides but is stable in the absence of added copper. Thus, an allylic THP group

  通过开发烯丙基四氢吡喃基醚与有机金属试剂的区域选择性偶联，已经高收率地合成了带有芳环的法呢醇类似物家族。在卤化铜（I）存在下，格利雅试剂容易使烯丙基THP基团置换，但在不添加铜的情况下稳定。因此，取决于反应条件，烯丙基THP基团可以履行其传统的保护基或离去基团的作用。还使用该方法完成了（2E，6E）-10,11-二氢法尼醇的改进合成，并对THP醚置换的反应性和区域选择性进行了一些初步研究。