2,4-bis(1,1-dibromoethyl)thiazole | 1028539-29-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2,4-bis(1,1-dibromoethyl)thiazole
• 英文别名: 2,4-Bis(1,1-dibromoethyl)-1,3-thiazole；2,4-bis(1,1-dibromoethyl)-1,3-thiazole
• CAS: 1028539-29-8
• 化学式: C₇H₇Br₄NS
• 分子量: 456.821
• InChiKey: WCMCHLHDEXTLBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  41.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4-bis(1,1-dibromoethyl)thiazole 在 silver nitrate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.33h， 以49%的产率得到2,4-diacetylthiazole
  参考文献：
  名称：

  Synthesis of 2,4-diacetylthiazole and 2,5-diacetylthiazole

  摘要：

  Compounds 2,4-diacetylthiazole 5 and 2,5-diacetylthiazole 6, of interest for their flavour and aroma properties, have been prepared for the first time by tetrabromination and silver nitrate treatment of the corresponding diethylthiazoles. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.064
• 作为产物：
  描述：

  2,4-二乙基-1,3-噻唑 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 various solvent(s) 为溶剂， 反应 7.0h， 以23.7 g的产率得到2,4-bis(1,1-dibromoethyl)thiazole
  参考文献：
  名称：

  Synthesis of 2,4-diacetylthiazole and 2,5-diacetylthiazole

  摘要：

  Compounds 2,4-diacetylthiazole 5 and 2,5-diacetylthiazole 6, of interest for their flavour and aroma properties, have been prepared for the first time by tetrabromination and silver nitrate treatment of the corresponding diethylthiazoles. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.064

文献信息

• The X-ray Structures of 2,4-Dibromothiazole and 2,4-Diacetyl-5-bromothiazole
  作者：Kati M. Aitken、R. Alan Aitken、Callum I. MacGregor、Mohamed D. M. Traore、Alexandra M. Z. Slawin

  DOI：10.1007/s10870-015-0615-x

  日期：2015.12

  2,4-Dibromothiazole [orthorhombic, a = 6.700 (10), b = 16.21 (3), c = 5.516 (8) Å, space group Fmm2] shows a disordered crystal structure with molecules randomly oriented with respect to the direction of the Br–C(2)–N–C(2)–Br unit and the remaining ring atoms S(3) and C(3)H showing mixed occupancy. 2,4-Diacetyl-5-bromothiazole [triclinic, a = 4.040 (2), b = 8.254 (5), c = 13.208 (8) Å, α = 96.191 (17), β = 93.865 (16), γ = 94.067 (11)°, space group P-1] shows a structure dominated by halogen bonding, intramolecular between 4-COMe and 5-Br and intermolecular between 2-COMe of one molecule and 5-Br of the next. 2,4-Dibromothiazole is disordered in the crystal structure with molecules randomly oriented either way round as shown. There is evidence for unusual intramolecular, and perhaps also intermolecular, halogen bonding between Br and C = O in the structure of 2,4-diacetyl-5-bromothiazole.

  2,4-二溴噻唑 [正交，a = 6.700 (10)，b = 16.21 (3)，c = 5.516 (8) Å, 空间群 Fmm2] 显示出无序的晶体结构，分子相对于 Br-C(2)-N-C(2)-Br 单元的方向随机定向，其余环原子 S(3) 和 C(3)H 显示出混合占有。2,4-二乙酰基-5-溴噻唑 [三菱形，a = 4.040 (2)，b = 8.254 (5)，c = 13.208 (8) 埃，α = 96.191 (17)，β = 93.865 (16)，γ = 94.067 (11)°，空间群 P-1]显示出以卤素键为主的结构，4-COMe 和 5-Br 之间为分子内键，一个分子的 2-COMe 和下一个分子的 5-Br 之间为分子间键。如图所示，2,4-二溴噻唑在晶体结构中是无序的，分子的方向是随机的。有证据表明，在 2,4-二乙酰基-5-溴噻唑的结构中，Br 和 C = O 之间存在不寻常的分子内卤素键，或许还有分子间卤素键。
• Synthesis of 2,4-diacetylthiazole and 2,5-diacetylthiazole
  作者：Kati M. Aitken、R. Alan Aitken

  DOI：10.1016/j.tet.2008.02.064

  日期：2008.5

  Compounds 2,4-diacetylthiazole 5 and 2,5-diacetylthiazole 6, of interest for their flavour and aroma properties, have been prepared for the first time by tetrabromination and silver nitrate treatment of the corresponding diethylthiazoles. (c) 2008 Elsevier Ltd. All rights reserved.