1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene | 878658-70-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene
• 英文别名: 8-[3-[2-(3-Quinolin-8-ylsulfanylprop-1-ynyl)phenyl]prop-2-ynylsulfanyl]quinoline；8-[3-[2-(3-quinolin-8-ylsulfanylprop-1-ynyl)phenyl]prop-2-ynylsulfanyl]quinoline
• CAS: 878658-70-9
• 化学式: C₃₀H₂₀N₂S₂
• 分子量: 472.634
• InChiKey: NXWZFUNLFFOJJL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tetrakis(acetonitrile)palladium(II) tetrafluoroborate 、 1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene 以 氯仿 、 乙腈 为溶剂， 以90%的产率得到[Pd(1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene)](BF4)2
  参考文献：
  名称：

  Thioether coordinated metalloenediynes: Syntheses, structures and thermal reactivity comparison

  摘要：

  Two novel, thioether containing benzannulated enediyne ligands, 1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene (1), and 1,2-bis(3-(pyridin-2-ylmethylsulfanyl)prop-I-ynyl)benzene (2) have been synthesized and characterized along with their corresponding Cu(I), Ag(I), Cu(II), and Pd(II) metalloenediyne complexes (3-10). Single crystal X-ray structures of the d(10) and d(8) N2S2 complexes show thioether coordination leading to distorted tetrahedral and trans square planar geometries about the metal centers, respectively. Based on their X-ray structures, all complexes are expected to exhibit high Bergman cyclization temperatures (> 200 degrees C), and indeed this is the case for the Cu(I) and Ag(I) complexes (211-218 degrees C). In contrast, the corresponding divalent, tetragonal and trans square planar complexes of Cu(II) and Pd(II) exhibit more facile reactivity and lower solid state Bergman cyclization temperatures (186-190 degrees C) which more closely resemble values expected for cis-complexes. The unusual order in the thermal reactivities of these constructs can be attributed to a previously evaluated mechanism by which weak thioether coordination permits an elevated temperature trans-to-cis geometric rearrangement prior to Bergman cyclization. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2005.07.032

文献信息

• Thioether coordinated metalloenediynes: Syntheses, structures and thermal reactivity comparison
  作者：Sibaprasad Bhattacharyya、Maren Pink、John C. Huffman、Jeffrey M. Zaleski

  DOI：10.1016/j.poly.2005.07.032

  日期：2006.1

  Two novel, thioether containing benzannulated enediyne ligands, 1,2-bis(3-(quinolin-8-ylsulfanyl)prop-1-ynyl)benzene (1), and 1,2-bis(3-(pyridin-2-ylmethylsulfanyl)prop-I-ynyl)benzene (2) have been synthesized and characterized along with their corresponding Cu(I), Ag(I), Cu(II), and Pd(II) metalloenediyne complexes (3-10). Single crystal X-ray structures of the d(10) and d(8) N2S2 complexes show thioether coordination leading to distorted tetrahedral and trans square planar geometries about the metal centers, respectively. Based on their X-ray structures, all complexes are expected to exhibit high Bergman cyclization temperatures (> 200 degrees C), and indeed this is the case for the Cu(I) and Ag(I) complexes (211-218 degrees C). In contrast, the corresponding divalent, tetragonal and trans square planar complexes of Cu(II) and Pd(II) exhibit more facile reactivity and lower solid state Bergman cyclization temperatures (186-190 degrees C) which more closely resemble values expected for cis-complexes. The unusual order in the thermal reactivities of these constructs can be attributed to a previously evaluated mechanism by which weak thioether coordination permits an elevated temperature trans-to-cis geometric rearrangement prior to Bergman cyclization. (c) 2005 Elsevier Ltd. All rights reserved.