1,8-diphenylocta-3,5-diyne | 22557-06-8

• 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: 1,8-diphenylocta-3,5-diyne
• 英文别名: 8-Phenylocta-3,5-diynylbenzene
• CAS: 22557-06-8
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: UTNPPKQXXVMYLG-UHFFFAOYSA-N

物化性质

• 沸点：
  432.0±34.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  1,8-diphenylocta-3,5-diyne 在 一氯化碘 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以90%的产率得到2,2'-diiodo-3,3',4,4'-tetrahydro-1,1'-binaphthalene
  参考文献：
  名称：

  ICl-Mediated Intramolecular Twofold Iodoarylation of Diynes and Diynyl Diethers and Amines: Synthesis of Bis(2H-hydronaphthalene and chromene) and 2H-Quinoline Bearing an Alkenyl Iodide Moiety

  摘要：

  Electrophilic intramolecular twofold iodoarylation was developed from the reaction of diynes and diynyl diethers and amines with iodine monochloride under mild conditions, which produced bis(2H-hydronaphthalene and chromene) and 2H-quinoline bearing an alkenyl iodide moiety in good to excellent yields. These compounds underwent Pd-catalyzed cross-coupling reactions with arylboronic acid and indium tris(arylthiolate) to produce the functionalized styrene derivatives.

  DOI：

  10.1021/jo401922b
• 作为产物：
  描述：

  4-苯基-1-丁炔 在 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 1.5h， 以96%的产率得到1,8-diphenylocta-3,5-diyne
  参考文献：
  名称：

  Cu(ii) complex heterogenized on SBA-15: a highly efficient and additive-free solid catalyst for the homocoupling of alkynes

  摘要：

  一个Cu(II)复合物通过对SBA-15进行功能化，使用(N1-丙基乙烯-1,2-二胺)三乙氧基硅烷(NN-SBA-15)，然后通过香豆素基形成将2-吡啶甲醛锚定在终端–NH2和2-吡啶甲醛的醛基之间（Py-NN-SBA-15），最终通过络合物固定了铜(II)。在SBA-15上异质化的铜(II)复合物(Cu(II)-SBA-15)已通过多种技术进行全面表征，如N2吸附、小角X射线衍射(XRD)、热重分析(TGA)、X射线光电子能谱(XPS)、透射电子显微镜(TEM)和固态13C CP-MAS NMR谱。Cu(II)-SBA-15是一种高效的异质固体催化剂，用于苯乙炔的氧化偶联反应，生成1,4-二苯基丁-1,3-二炔，产率为97%，甚至在没有钯、合催化剂和碱添加剂的情况下。在其他芳香族和脂肪族末端炔烃的偶联反应中，产率为85–98%。

  DOI：

  10.1039/c3ra44213f

文献信息

• A General and Highly Selective Palladium‐Catalyzed Hydroamidation of 1,3‐Diynes
  作者：Jiawang Liu、Carolin Schneider、Ji Yang、Zhihong Wei、Haijun Jiao、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.202010768

  日期：2021.1.4

  3‐diynes is described. Key for the success of this novel transformation is the utilization of an advanced palladium catalyst system with the specific ligand Neolephos. The synthetic value of this general approach to synthetically useful α‐alkynyl‐α, β‐unsaturated amides is showcased by diversification of several structurally complex molecules and marketed drugs. Control experiments and density‐functional

  描述了（不）对称 1,3-二炔的化学选择性、区域选择性和立体选择性单氢酰胺化。这种新型转化成功的关键是采用具有特定配体 Neolephos 的先进钯催化剂系统。这种合成有用的 α-炔基-α, β-不饱和酰胺的通用方法的合成价值通过几种结构复杂的分子和上市药物的多样化得到了展示。控制实验和密度泛函理论 (M06L-SMD) 计算也表明底物在控制不对称 1,3-二炔的区域选择性中发挥着关键作用。
• Visual and tear function improvement after superficial phototherapeutic keratectomy (PTK) for mid-stromal corneal scarring
  作者：Murat Dogru、Chikako Katakami、Masato Miyashita、Etsuko Hida、Mamoru Uenishi、Kazuaki Tetsumoto、Sanae Kanno、Teruo Nishida、Akio Yamanaka

  DOI：10.1038/eye.2000.204

  日期：2000.9

  Purpose To study the changes in visual and tear film function following superficial excimer laser phototherapeutic keratectomy in patients with mid-stromal corneal scars. Methods Fourteen eyes of 14 patients with mid-stromal corneal scars seen at the Department of Ophthalmology at Kobe Kaisei Hospital underwent superficial phototherapeutic keratectomy (PTK). The subjects underwent routine ophthalmic examinations, corneal sensitivity measurements, tear film break-up time (BUT), Schirmer test and tear film lipid layer interferometry. Thirty eyes of 15 normal control subjects were also studied. The patients and the control subjects were compared for pre-PTK tear function parameters and tear film lipid layer interferometry grade. The alterations in these parameters within 6 months following PTK were also determined. Results Visual improvement was achieved in 12 eyes (86%). A hyperopic shift was observed in all eyes. The average pre-PTK corneal sensitivity and tear film BUT were lower in patients compared with control subjects before PTK. Tear film lipid layer interferometry grades were also higher in the patients than the controls before PTK. All these parameters improved gradually and significantly after PTK. Schirmer test results did not show any significant alterations after PTK. Conclusion We conclude that PTK is an effective means of treating corneal scars and attaining visual improvement, even in cases with deeper corneal involvement, and may obviate the need for corneal transplantation. Simultaneous improvements in corneal sensitivity and tear film stability suggest favourable effects of PTK on the ocular surface.

  目的：研究浅层准分子激光角膜切削术(PTK)后，中层基质性角膜瘢痕患者视觉和泪膜功能变化。方法：在神户海星医院眼科，14名中层基质性角膜瘢痕患者接受浅层PTK手术，共14眼。术前进行常规眼科检查，测量角膜敏感性、泪膜破裂时间(BUT)、泪液分泌测试和泪膜脂质层干涉测量。还研究了15例正常对照者的共30眼。比较术前患者和对照者的泪膜功能参数和泪膜脂质层干涉测量分级。术后6个月内这些参数的变化也进行了研究。结果：12眼(86%)改善了视力。所有眼出现远视漂移。术前患者角膜敏感性和泪膜BUT低于对照组。术前患者的泪膜脂层干涉测量分级高于对照组眼。这些参数术后逐渐显著提高。PTK后Schaumberg试验结果没有显著变化。结论：，结论:我们认为PTK是治疗角膜瘢痕并获得视力提高的有效方法，即便是伴有更深层角膜病变者，并且可能不再需要进行角膜移植。角膜敏感性和泪膜稳定性同时提高，表明PTK对眼表有良好的效应。
• Tailored Palladium Catalysts for Selective Synthesis of Conjugated Enynes by Monocarbonylation of 1,3‐Diynes
  作者：Jiawang Liu、Ji Yang、Carolin Schneider、Robert Franke、Ralf Jackstell、Matthias Beller

  DOI：10.1002/anie.201915386

  日期：2020.6.2

  1'-binaphthalene (Neolephos), which permits the palladium-catalyzed selective carbonylation under mild conditions, providing a general preparation of functionalized 1,3-enynes in good-to-high yields with excellent chemoselectivities. Synthetic applications that showcase the possibilities of this novel methodology include an efficient one-pot synthesis of 4-aryl-4H-pyrans as well as the rapid construction of various

  首次实现了容易获得的 1,3-二炔的单烷氧基羰基化以产生合成有用的共轭烯炔。成功的关键是设计和利用新配体 2,2'-双(叔丁基(吡啶-2-基)膦基)-1,1'-联萘 (Neolephos)，它允许钯催化选择性羰基化在温和条件下，以良好到高的产率提供官能化 1,3-烯炔的通用制备，并具有优异的化学选择性。展示这种新方法可能性的合成应用包括 4-芳基-4H-吡喃的高效一锅法合成以及各种杂环、双环和多环化合物的快速构建。
• Ligand-accelerating low-loading copper-catalyzed effective synthesis of (E)-1,3-enynes by coupling between vinyl halides and alkynes performed in water
  作者：Peng Sun、Hong Yan、Linhua Lu、Defu Liu、Guangwei Rong、Jincheng Mao

  DOI：10.1016/j.tet.2013.06.063

  日期：2013.8

  The useful conjugated enynes could be easily prepared via low-loading (0.0001 mol %) copper-catalyzed coupling between vinyl halides and terminal alkynes. It is noteworthy that this reaction could be preformed in water without using any co-solvents and the desired 1,3-enynes could be obtained with good yields. In the catalytic reaction, ligand-acceleration effect was markable.

  有用的共轭烯炔可以通过乙烯基卤化物和末端炔烃之间的低负载（0.0001 mol％）铜催化的偶联容易地制备。值得注意的是，该反应可以在水中进行而无需使用任何助溶剂，并且可以良好的收率获得所需的1，3-烯炔。在催化反应中，配体促进作用是显着的。
• Regio‐ and Diastereoselective Copper‐Catalyzed Carbomagnesiation for the Synthesis of Penta‐ and Hexa‐Substituted Cyclopropanes
  作者：Yair Cohen、André U. Augustin、Laura Levy、Peter G. Jones、Daniel B. Werz、Ilan Marek

  DOI：10.1002/anie.202102509

  日期：2021.5.17

  Despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters, the regio‐ and diastereoselective copper‐catalyzed carbomagnesiation reaction of cyclopropenes provides an easy and efficient access to these novel persubstituted cyclopropyl cores with a complete regio‐ and diastereoselectivity.

  尽管具有三个邻位季铵碳立体中心的环丙烷具有很高的应变特性，但区域和非对映选择性铜催化的碳镁碳环化反应仍可轻松有效地获得这些具有完整区域和非对映选择性的新型取代环丙基。