1-phenylocta-1,3-diyne | 62217-45-2

• 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-phenylocta-1,3-diyne
• 英文别名: octa-1,3-diyn-1-ylbenzene；Benzene, 1,3-octadiynyl-；octa-1,3-diynylbenzene
• CAS: 62217-45-2
• 化学式: C₁₄H₁₄
• 分子量: 182.265
• InChiKey: GFZZPFUTRBRBCJ-UHFFFAOYSA-N

物化性质

• 沸点：
  91-93 °C(Press: 0.01 Torr)
• 密度：
  0.96±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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-phenylocta-1,3-diyne 在 selenium 、 碘 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 24.17h， 生成 2-(n-butyl)-3-iodo-5-phenylselenophene
  参考文献：
  名称：

  Electrophilic Cyclization of (Z)-Selenoenynes:  Synthesis and Reactivity of 3-Iodoselenophenes

  摘要：

  We present here our results of the electrophilic cyclization reaction of (Z)-selenoenynes with different electrophiles such as I-2, ICl, PhSeBr, and PhSeCl. The cyclization reaction proceeded cleanly under mild reaction conditions, and 3-substituted selenophenes were formed in moderate to excellent yields. We observed that the nature of solvent and structure of (Z)-selenoenyne were important to the cyclization reaction. In addition, the obtained 3-iodoselenophenes were readily transformed to more complex products using a metal-halogen exchange reaction with n-BuLi and trapping the intermediate formed with aldehydes, furnishing the desired secondary alcohols in good yields. Conversely, using the palladium or copper catalyzed cross-coupling reactions with terminal alkynes or alkyl alcohols, we were able to convert 3-iodoselenophene to Sonogashira or Ullmann type products, respectively, in good yields.

  DOI：

  10.1021/jo070835t
• 作为产物：
  描述：

  phenylpropiolyl chloride 在 正丁基锂 作用下， 反应 3.5h， 生成 1-phenylocta-1,3-diyne
  参考文献：
  名称：

  Flash vacuum pyrolysis of stabilised phosphorus ylides. Part 8. Preparation of symmetrical and unsymmetrical 1,3-diynes from alkynoyl ylides and oxalyl diylides

  摘要：

  Seven examples of the alkynoyl phosphorus ylides 5 have been prepared and are found, upon flash vacuum pyrolysis (FVP) at 750 degrees C, to undergo extrusion of Ph(3)PO to give the unsymmetrical 1,3-diynes 9 in moderate yield. Six examples of the oxalyl diylides 6 have been prepared and their fully assigned C-13 NMR spectra are presented. Upon FVP, those with R = aryl undergo two-fold extrusion of Ph(3)PO to give symmetrical 1,3-diynes 13 but this requires the unusually severe temperature of 900 degrees C. In contrast those with R = CO(2)Me, CO(2)Et or COPh undergo complete reaction at 500 degrees C but afford only Ph(3)PO and fragmentation products.

  DOI：

  10.1039/p19960000485

文献信息

• Palladium-catalysed cross-coupling reactions of aryl-, alkenyl- and alkynyl-iodonium salts and iodanes with terminal alkynes in aqueous medium
  作者：Suk-Ku Kang、Hong-Woo Lee、Su-Bum Jang、Pil-Su Ho

  DOI：10.1039/cc9960000835

  日期：——

  The ligand-free Pd(OAc)2-catalysed coupling reaction of aryl-, alkenyl- and alkynyl-iodonium tetraflouroborate and iodanes with terminal alkynes proceeds readily in the presence of NaHCO2 in aqueous medium to afford the substituted alkynes in high yields under mild conditions.

  在没有配体的情况下，Pd(OAc)2催化的芳基、烯基和炔基碘鎓四氟硼酸盐与末端炔烃的碘化物在NaHCO2存在下的水相中顺利进行反应，在温和条件下高效地获得了取代炔烃。
• Palladium-Catalyzed [4+2] <i>Cross</i>-Benzannulation Reaction of Conjugated Enynes with Diynes and Triynes
  作者：Vladimir Gevorgyan、Akira Takeda、Miyako Homma、Naoki Sadayori、Ukkiramapandian Radhakrishnan、Yoshinori Yamamoto

  DOI：10.1021/ja990749d

  日期：1999.7.1

  4-trisubstituted benzenes 8a−j, 1,2,3-trisubstituted benzenes 9a−i, 1,2,3,5-tetrasubstituted benzenes 11a−k, 1,2,3,4-tetrasubstituted benzenes 11l,m, and 1,2,3,4,5-pentasubstituted benzenes 11n−p in moderate to quantitative yields. In all cases the reaction was found to be regiospecific with regard to substitution at the benzene ring. The palladium-catalyzed [4+2] cycloaddition of monosubstituted conjugated

  在 Pd(0) 催化剂存在下，烯-二炔 [4+2] 交叉苯并顺利进行，得到 1,2,4-三取代苯 8a-j, 1,2,3-三取代苯 9a-i, 1 ,2,3,5-四取代苯 11a-k、1,2,3,4-四取代苯 11l,m 和 1,2,3,4,5-五取代苯 11n-p，产率中等至定量。在所有情况下，发现该反应在苯环取代方面具有区域特异性。钯催化的单取代共轭烯炔 3a-c 和 5a 与不对称二炔 13a-j 和三炔 16a-g 的 [4+2] 环加成也进行了关于苯环取代的完美区域化学。然而，由于亲烯体 13 和 16 中存在两个不同取代的三键，烯炔对亲烯体中任一三键的偏好成为一个问题，在大多数情况下，获得了两种区域异构产品。进行了详细的氘标记研究，并了解了这种区域特异性 [4...
• Intermolecular [3+2] Annulation of Cyclopropylanilines with Alkynes, Enynes, and Diynes<i>via</i>Visible Light Photocatalysis
  作者：Theresa H. Nguyen、Scott A. Morris、Nan Zheng

  DOI：10.1002/adsc.201400742

  日期：2014.9.15

  simple starting materials remain rare. We recently developed an intermolecular [3+2] annulation of cyclopropylanilines with alkenes and alkynes that enables this one‐step synthesis. Herein, we report our findings for a full‐scale study of the annulation. Significant expansion of the substrate scope for both cyclopropylanilines and alkynes has been achieved. A range of structurally diverse carbocycles

  由简单的起始原料一步一步合成被胺取代的碳环仍然很少。最近，我们开发了环丙基苯胺与烯烃和炔烃的分子间[3 + 2]环合反应，可实现这一一步合成。在此，我们报告我们的发现，以对环空进行全面研究。环丙基苯胺和炔烃的底物范围已得到显着扩大。制备了一系列结构上被胺取代的碳环。
• Hydroselenation of Alkynes by Lithium Butylselenolate:  An Approach in the Synthesis of Vinylic Selenides
  作者：Gilson Zeni、Marcelo P. Stracke、Cristina W. Nogueira、Antonio L. Braga、Paulo H. Menezes、Helio A. Stefani

  DOI：10.1021/ol0498904

  日期：2004.4.1

  Vinylic selenides were prepared in good yields by hydroselenation of alkynes with lithium butylselenolate generated by reaction of n-butyllithium with elemental selenium. The regio- and stereochemistry of the hydroselenation depend on the nature of the substituents bonded to the alkyne.

  通过炔烃与正丁基锂与元素硒反应生成的丁基硒化锂进行氢硒化，可以制备高产率的乙烯基硒化物。加氢硒化的区域化学和立体化学取决于与炔烃键合的取代基的性质。
• Aldehyde Addition to 1,3-Butadiyne-Derived Zirconacyclocumulenes: Stereoselective Synthesis of <i>cis</i>-[3]Cumulenols
  作者：Xiaoping Fu、Yuanhong Liu、Yuxue Li

  DOI：10.1021/om100287d

  日期：2010.7.12

  1,3-butadiynes is achieved cleanly under controlled reaction conditions, which provids a highly stereoselective method for the synthesis of tetra-substituted [3]cumulenols. DFT calculations suggest that there is an equilibrium between seven-membered zirconacyclocumulene (3) and the less stable but more reactive five-membered α-alkynylzirconaindene (2) in the process. The aldehyde reacts with the five-membered

  在受控的反应条件下，可以很干净地将醛直接加到通过苯并锆茂茂与1,3-丁二炔的偶合反应生成的氧化锆环枯烯中，为合成四取代的[3]枯烯醇提供了高度立体选择性的方法。DFT计算表明，在此过程中，七元氧化锆环枯烯（3）与较不稳定但反应性更高的五元α-炔基氧化锆茚（2）之间存在平衡。醛通过环状S E 2'途径与五元氧化锆茚中间体反应，水解后得到枯草烯醇产物。