3-溴-2-[(3-溴噻吩-2-基)甲基]噻吩 | 17965-59-2

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 中文名称: 3-溴-2-[(3-溴噻吩-2-基)甲基]噻吩
• 英文名称: 3,3'-Dibromo-2,2'-dithienylmethane
• 英文别名: bis(3-bromo-2-thienyl)methane；3,3'-dibromo-2,2'-methanediyl-bis-thiophene；Bis(3-bromothiophen-2-yl)methane；3-bromo-2-[(3-bromothiophen-2-yl)methyl]thiophene
• CAS: 17965-59-2
• 化学式: C₉H₆Br₂S₂
• 分子量: 338.087
• InChiKey: QFUWWMYEZXFRSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-溴-2-[(3-溴噻吩-2-基)甲基]噻吩 在 正丁基锂 、 氧气 作用下， 以 四氢呋喃 为溶剂， 以45%的产率得到5,9,16,20-Tetrathiapentacyclo[17.3.0.02,6.08,12.013,17]docosa-1(19),2(6),3,8(12),10,13(17),14,21-octaene
  参考文献：
  名称：

  氰基-吉尔曼铜酸盐的选择性：10元环环烷的合成

  摘要：

  氰基-吉尔曼铜酸盐（衍生自二溴二噻吩基硫化物、二溴二噻吩基二甲基硅烷和二溴二噻吩基甲烷）与分子氧的氧化选择性地提供了 10 元环环烷，环烷 9 的 X 射线分析表明它具有反构象。

  DOI：

  10.1039/b008102g
• 作为产物：
  描述：

  3-溴噻吩 、 甲氧基乙酰氯 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 以45%的产率得到3-溴-2-[(3-溴噻吩-2-基)甲基]噻吩
  参考文献：
  名称：

  一种简单且廉价的方法，用于某些芳香族化合物的氯甲基化

  摘要：

  一系列芳族化合物与甲氧基乙酰氯和氯化铝在硝基甲烷或二硫化碳中的反应导致氯甲基化，收率好至极佳。

  DOI：

  10.1016/s0040-4039(00)81809-2

文献信息

• Synthesis of dithienothiophenes, cyclopentadithiophene and silacyclopentadithiophenes using palladium-catalyzed cyclization
  作者：Masahiko Iyoda、Mami Miura、Shigeru Sasaki、S.M.Humayun Kabir、Yoshiyuki Kuwatani、Masato Yoshida

  DOI：10.1016/s0040-4039(97)00979-9

  日期：1997.6

  The intramolecular cyclization of bromothiophene derivatives with hexamethylditin in the presence of tetrakis(triphenylphosphine)palladium(0) gave dithienothiophenes, cyclopentadithiophene, and silacyclopentadithiophenes in moderate to good yields.

  在四（三苯基膦）钯（0）​​存在下，溴化噻吩衍生物与六甲基二锡的分子内环化反应以中等至良好的产率得到了二噻吩并噻吩，环戊二噻吩和硅环戊二噻吩。
• Kabir, S. M. Humayun; Miura, Mami; Sasaki, Shigeru, Heterocycles, 2000, vol. 52, # 2, p. 761 - 774
  作者：Kabir, S. M. Humayun、Miura, Mami、Sasaki, Shigeru、Harada, Genta、Kuwatani, Yoshiyuki、Yoshida, Masato、Iyoda, Masahiko

  DOI：——

  日期：——
• Efficient Construction of Biaryls and Macrocyclic Cyclophanes via Electron-Transfer Oxidation of Lipshutz Cuprates
  作者：Yoshihiro Miyake、Mo Wu、M. Jalilur Rahman、Yoshiyuki Kuwatani、Masahiko Iyoda

  DOI：10.1021/jo0608063

  日期：2006.8.1

  An efficient method for the homocoupling of aryl halides by electron-transfer oxidation of Lipshutz cuprates (Ar2Cu(CN)Li-2) with organic electron acceptors is disclosed. Thus, various types of Lipshutz cuprates are prepared by successive treatment of aryl or heteroaryl bromides with tert-butyllithium and CuCN. The electron-transfer oxidation of Lipshutz cuprates with p-benzoquinones proceeds smoothly to afford the corresponding homocoupling products in moderate to good yields. Furthermore, it can be applied to the construction of either thiophene- or benzene-fused 10-membered ring cyclophanes. For the synthesis of 10-membered cyclophanes, the linear C-Cu-C structure of Lipshutz cuprates should be maintained in the dimetallacyclic intermediates, producing the large ring cyclophanes efficiently. The X-ray analysis of the cyclophanes reveals that the difference in the bridging atoms results in the different conformations of the macrocyclic rings. Thus, the silicon-bridged cyclophane 5a adopts a D-2-symmetric structure with a twisted rhombic arrangement of four thiophene rings, whereas the methylene- and oxygen-bridged cyclophanes 5b and 5c possess C2h- and C-2-symmetric structures with chair- and boatlike conformations, respectively. The H-1 NMR spectrum of C-2-symmetric 5c is temperature- dependent, and the activation energy (Delta G double dagger) for the conformational change is 10.1 kcal/mol.
• MCKILLOP, A.;MADJDABADI, FERREIDON, ABBASI;LONG, D. A., TETRAHEDRON LETT., 1983, 24, N 18, 1933-1936
  作者：MCKILLOP, A.、MADJDABADI, FERREIDON, ABBASI、LONG, D. A.

  DOI：——

  日期：——
• A simple and inexpensive procedure for chloromethylation of certain aromatic compounds
  作者：Alexander McKillop、Fereidon Abbasi Madjdabadi、David A. Long

  DOI：10.1016/s0040-4039(00)81809-2

  日期：1983.1

  Reaction of a range of aromatic compounds with methoxyacetyl chloride and aluminium chloride in either nitromethane or carbon disulphide results in chloromethylation in good to excellent yield.

  一系列芳族化合物与甲氧基乙酰氯和氯化铝在硝基甲烷或二硫化碳中的反应导致氯甲基化，收率好至极佳。