1,6-dimethyl-1,6-diphenylhexa-2,4-diyne-1,6-diol | 62051-68-7

• 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: 1,6-dimethyl-1,6-diphenylhexa-2,4-diyne-1,6-diol
• 英文别名: meso-2,7-diphenyl-3,5-octadiyne-2,7-diol；2,7-diphenyl-3,5-octadiyne-2,7-diol；2,7-diphenylocta-3,5-diyne-2,7-diol；2,7-diphenyl-octa-3,5-diyne-2,7-diol；2,7-Diphenyl-octa-3,5-diin-2,7-diol；2.7-Dihydroxy-2.7-diphenyl-octadiin-(3.5)；3,5-Octadiyne-2,7-diol, 2,7-diphenyl-
• CAS: 62051-68-7
• 化学式: C₂₀H₁₈O₂
• 分子量: 290.362
• InChiKey: TTXACJSKPHFKQD-UHFFFAOYSA-N

物化性质

• 熔点：
  195 °C
• 沸点：
  494.7±45.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  22
• 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：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,6-dimethyl-1,6-diphenylhexa-2,4-diyne-1,6-diol 在 三苯基膦 作用下， 以 甲苯 为溶剂， 以51%的产率得到1,6-diphenylhepta-4,5-dien-2-yn-1-ol
  参考文献：
  名称：

  通过磷烷介导的 2,4-戊二炔-1-醇脱氧合成三取代的艾伦炔

  摘要：

  已开发出一种合成三取代丙炔的简便方法。该过程涉及磷烷介导的 2,4-戊二炔-1-醇衍生物的脱氧。多种炔丙醇可以在温和的反应条件下以中等至良好的产率转化为丙炔。

  DOI：

  10.1002/ejoc.201000483
• 作为产物：
  描述：

  丁二炔 在 氨 、 sodium amide 作用下， 生成 1,6-dimethyl-1,6-diphenylhexa-2,4-diyne-1,6-diol
  参考文献：
  名称：

  Armitage et al., Journal of the Chemical Society, 1951, p. 44,47

  摘要：

  DOI：

文献信息

• PMHS-Mediated Couplings of Alkynes or Benzothiazoles with Various Electrophiles:  Application to the Synthesis of (−)-Akolactone A
  作者：William P. Gallagher、Robert E. Maleczka

  DOI：10.1021/jo034463+

  日期：2003.8.1

  Polymethylhydrosiloxane (PMHS) in combination with CsF facilitates the cross-coupling of alkynes or benzothiazoles with an array of vinyl, styryl, and aryl halides or nonaflates as well as acid chlorides. Experimental and spectroscopic evidence indicates that these reactions involve the in situ generation of a siloxyl intermediate. These cross-couplings proceed relatively quickly at room temperature

  聚甲基氢硅氧烷（PMHS）与CsF的结合有助于炔烃或苯并噻唑与一系列乙烯基，苯乙烯基和芳基卤化物或壬二酸酯以及酰基氯的交叉偶联。实验和光谱证据表明，这些反应涉及甲硅烷氧基中间体的原位生成。这些交叉偶联在室温和无胺条件下进行得相对较快。为了证明该方法的适用性，进行了全细胞毒性丁醇内酯（-）-可可内酯A的合成。
• Oxidative Coupling Reaction of Acetylene Compounds in the Solid State
  作者：Fumio Toda、Yoshihisa Tokumaru

  DOI：10.1246/cl.1990.987

  日期：1990.6

  Oxidative coupling of acetylene compound with cupric salt in the solid state was found to proceed efficiently and selectively. The coupling reaction of α,ω-diacetylenes in the solid state gave the linear oligomers in contrast with the formation of the cyclic products in the solution reaction.

  发现乙炔化合物与固态铜盐的氧化偶联有效且选择性地进行。与溶液反应中环状产物的形成相反，固态下的α,ω-二乙炔的偶联反应产生线性低聚物。
• Synthesis of Conjugated Diallenes by Double [2,3]-Sigmatropic Rearrangement of Conjugated Diyne Trichloromethanesulfenates
  作者：C. Paul Raj、S. Braverman

  DOI：10.1080/00397919908086424

  日期：1999.8.1

  trichloromethanesulfenyl chloride is described. The thus generated bis-propargylic trichloromethanesulfenates undergo spontaneous double [2,3]-sigmatropic rearrangement which leads to the formation of conjugated diallenic trichloromethyl sulfoxides in good to excellent yields.

  摘要 描述了几种 2,4-二炔-1,6-二醇的制备及其与三氯甲磺酰氯的酯化反应。如此生成的双炔丙基三氯甲磺酸盐发生自发的双 [2,3]-σ 重排，导致以良好至极好的产率形成共轭二烯三氯甲基亚砜。
• Cu(<scp>ii</scp>) complex heterogenized on SBA-15: a highly efficient and additive-free solid catalyst for the homocoupling of alkynes
  作者：Anand Narani、Ravi Kumar Marella、Pochamoni Ramudu、Kamaraju Seetha Rama Rao、David Raju Burri

  DOI：10.1039/c3ra44213f

  日期：——

  A Cu(II) complex has been heterogenized on SBA-15 by functionalization of SBA-15 with (N1-propylethane-1,2-diamine) triethoxysilane (NN-SBA-15) followed by anchoring of 2-pyridinecarboxaldehyde through Schiff's base formation between the terminal –NH2 and the aldehyde group of 2-pyridinecarboxaldehyde (Py-NN-SBA-15), and finally, copper(II) was immobilized through complexation. Copper(II) complex heterogenized on SBA-15 (Cu(II)-SBA-15) has been thoroughly characterized by different techniques such as N2 sorption, small-angle X-ray diffraction (XRD), thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), transmission electron microscopy (TEM) and solid-state 13C CP-MAS NMR spectroscopy. Cu(II)-SBA-15 is an efficient heterogenized solid catalyst for the oxidative homocoupling of phenyl acetylene into 1,4-diphenylbuta-1,3-diyne with a yield of 97%, even in the absence of palladium, co-catalyst and base additives. In the case of the homocoupling of other aromatic and aliphatic terminal alkynes, the yields were 85–98%.

  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%。
• Ligand- and Base-Free Synthesis of 1,3-Diynes Catalyzed by Low Loading of Heterogeneous Pd/C and CuI
  作者：Hironao Sajiki、Takanori Kurita、Masami Abe、Tomohiro Maegawa、Yasunari Monguchi

  DOI：10.1055/s-2007-986663

  日期：2007.10

  A facile and environmentally friendly synthetic method for a variety of symmetrical 1,3-diyne derivatives based on the Pd/C-CuI-catalyzed homocoupling reaction of terminal alkynes has been developed. The reaction was efficiently catalyzed by the ­extremely low loading (0.01-0.03 mol%) of Pd/C and CuI (3 mol%) in the presence of molecular oxygen (O2) as an oxidant without any phosphine ligands and bases.

  一种简便且环保的合成方法已被开发应用于多种对称的1,3-二炔衍生物，基于Pd/C-CuI催化的末端炔烃自偶联反应。该反应在分子氧（O2）作为氧化剂的存在下，高效催化，仅使用极低负载量（0.01-0.03 mol%）的Pd/C和3 mol%的CuI，无需任何膦配体和碱。