1-phenyl-8-(p-tolyl)-1,3,5,7-octatetrayne | 879560-20-0

• 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-phenyl-8-(p-tolyl)-1,3,5,7-octatetrayne
• 英文别名: Benzene, 1-methyl-4-(8-phenyl-1,3,5,7-octatetraynyl)-；1-methyl-4-(8-phenylocta-1,3,5,7-tetraynyl)benzene
• CAS: 879560-20-0
• 化学式: C₂₁H₁₂
• 分子量: 264.326
• InChiKey: QVZSMIVQMHQXQV-UHFFFAOYSA-N

物化性质

• 熔点：
  93-94 °C
• 沸点：
  415.0±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  (4-甲基苯基)炔丙醛 在 2,6-二甲基吡啶 、 正丁基锂 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.5h， 生成 1-phenyl-8-(p-tolyl)-1,3,5,7-octatetrayne
  参考文献：
  名称：

  Highly Efficient and Selective Synthesis of Conjugated Triynes and Higher Oligoynes of Biological and Materials Chemical Interest via Palladium-Catalyzed Alkynyl−Alkenyl Coupling

  摘要：

  Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH-CHCI followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.

  DOI：

  10.1021/ol0623825

文献信息

• A One-Pot Synthesis and Functionalization of Polyynes
  作者：Yasuhiro Morisaki、Thanh Luu、Rik R. Tykwinski

  DOI：10.1021/ol0528888

  日期：2006.2.1

  [reaction: see text] A one-pot synthesis and derivatization of diynes and triynes is reported. The polyyne framework is formed from a dibromoolefin precursor based on a carbenoid rearrangement, and the resulting Li-acetylide is then trapped in situ with an electrophile to provide functionalized di- and triynes. Alternatively, transmetalation of the Li-acetylide intermediate provides either the Zn-

  [反应：见正文]据报道，一锅法合成和衍生了二炔和三炔。聚炔骨架是由基于类胡萝卜素重排的二溴代烯烃前体形成的，然后用亲电子试剂将所得的乙炔基锂原位捕获，以提供官能化的二炔和三炔。备选地，Li-乙炔化物中间体的重金属化提供了Zn-或Sn-乙炔化物，其然后允许经由钯催化的交叉偶联反应而发散地制备二芳基聚炔或芳基炔酮。
• One-Pot Formation and Derivatization of Di- and Triynes Based on the Fritsch−Buttenberg−Wiechell Rearrangement
  作者：Thanh Luu、Yasuhiro Morisaki、Nina Cunningham、Rik R. Tykwinski

  DOI：10.1021/jo701810g

  日期：2007.12.1

  A divergent, one-pot synthesis of functionalized polyynes has been developed. Beginning with the appropriately substituted dibromoolefinic precursor, a carbenoid Fritsch−Buttenberg−Wiechell (FBW) rearrangement is used to generate the lithium acetylide of a conjugated polyyne framework, and subsequent trapping with carbon-based electrophiles provides for in situ formation of a wide range of di- and

  已经开发了一种发散的，一锅法合成的功能化多炔。从适当取代的二溴代烯烃前体开始，类胡萝卜素Fritsch-Buttenberg-Wiechell（FBW）重排用于生成共轭多炔骨架的乙炔锂，随后被碳基亲电试剂捕集，可在原位形成多种二炔和三炔。由FBW反应形成的乙炔锂也可以进行金属转移，以提供相应的锌，铜，锡或铂乙炔，导致对称和不对称共轭乙炔以及炔酮的发散形成。
• Highly Efficient and Selective Synthesis of Conjugated Triynes and Higher Oligoynes of Biological and Materials Chemical Interest via Palladium-Catalyzed Alkynyl−Alkenyl Coupling
  作者：Estelle Métay、Qian Hu、Ei-ichi Negishi

  DOI：10.1021/ol0623825

  日期：2006.12.1

  Iteration of a Pd-catalyzed reaction of alkynyl- and oligoynylzincs with (E)-ICH-CHCI followed by metalation-termination with electrophiles(E) has provided a linear route to conjugated tri- and tetraynes, and Pd-catalyzed monoalkynylation of 1,1-dibromoenynes accompanied by dehydrobromination has provided a convergent route to conjugated tri-, tetra-, and pentaynes. Both display unprecedented high efficiency and selectivity.