(1Z)-1-bromo-1-(2-thiazolyl)-1-octene | 656242-85-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (1Z)-1-bromo-1-(2-thiazolyl)-1-octene
• 英文别名: 2-[(Z)-1-bromooct-1-enyl]-1,3-thiazole
• CAS: 656242-85-2
• 化学式: C₁₁H₁₆BrNS
• 分子量: 274.225
• InChiKey: VVAGOIBNXVMMTN-YFHOEESVSA-N

物化性质

• 沸点：
  335.4±35.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 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：

  Dimethylzinc 、 (1Z)-1-bromo-1-(2-thiazolyl)-1-octene 在 二(三叔丁基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到(2E)-2-(2'-thiazolyl)-2-nonene
  参考文献：
  名称：

  Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

  摘要：

  Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2003.09.008
• 作为产物：
  描述：

  1,1-dibromo-1-octene 、 bromozinc(1+),2H-1,3-thiazol-2-ide 在 Cl₂Pd(DPEphos) 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以84%的产率得到(1Z)-1-bromo-1-(2-thiazolyl)-1-octene
  参考文献：
  名称：

  Pd-catalyzed selective tandem arylation–alkylation of 1,1-dihalo-1-alkenes with aryl- and alkylzinc derivatives to produce α-alkyl-substituted styrene derivatives

  摘要：

  Trans-selective monoarylation of 1, 1-dibromo- and 1,1-dichloro-1-alkenes (1) can be achieved in > 80% yields and in > 98-99% stereo selectivity with arylzinc bromides in the presence of a catalytic amount of Cl2Pd(DPEphos) or Cl2Pd(dppb), the former permitting cleaner and higher yielding reactions. Although THF is a generally satisfactory solvent, ether and toluene are superior to THF in some cases. The second substitution of (Z)-alpha-bromostyrenes (3) with alkylzincs in the presence of 2 mol% of Pd('Bu3P)(2) proceeds to give the corresponding 2 in >90% yields and in greater than or equal to98-99% stereoselectivity. Although somewhat less satisfactory, the use of Cl2Pd(DPEphos) permits a one-pot tandem arylation-alkylation. (C) 2003 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2003.09.008