(1,2-二溴-2-硝基丙基)苯 | 19419-13-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1,2-二溴-2-硝基丙基)苯
• 英文名称: erythro-dl-1,2-Dibromo-2-nitro-1-phenylpropane
• 英文别名: (1,2-Dibromo-2-nitropropyl)benzene
• CAS: 19419-13-7
• 化学式: C₉H₉Br₂NO₂
• 分子量: 322.984
• InChiKey: JCEVDZFOOWBQIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1,2-二溴-2-硝基丙基)苯 在 lithium perchlorate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 苯,(2-硝基-1-丙烯基)-,(E)-
  参考文献：
  名称：

  Electrochemical Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes in Dimethyl Sulfoxide

  摘要：

  Electrochemical debromination reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes 1a-d at a platinum electrode have been investigated by cyclic voltammetry in 0.10 M LiClO4/DMSO. The reactions produced (E)-1-aryl-2-nitropropenes 2a-d in high yields. The cyclic voltammograms were irreversible and the reduction current decreased as the number of cycles increased. The peak potential for the reductions waves are in the range of -0.51 to -0.56 V (vs Ag/Ag+) and show no clear trend with different aryl substituent. The current density increased as the concentration of the substrate increased. The slopes of the plots of log(I/A) vs log[C] are close to unity, indicating unimolecular processes. For all reactions, the Tafel slopes are in the range of 115-125 mV. The logarithm of the ratio i(X)/i(H) at -0.16 V did not correlate with the Hammett substituent constants. From these results, the mechanism of these reactions is assessed.

  DOI：

  10.1021/jo00112a031
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 溴 作用下， 生成 (1,2-二溴-2-硝基丙基)苯
  参考文献：
  名称：

  Priebs, Justus Liebigs Annalen der Chemie, 1884, vol. 225, p. 362

  摘要：

  DOI：
• 作为试剂：
  描述：

  N-苄基异丙胺 在 (1,2-二溴-2-硝基丙基)苯 作用下， 以 乙腈 为溶剂， 反应 48.0h， 以76%的产率得到N-苯亚甲基异丙醇胺
  参考文献：
  名称：

  Mechanism of Debromination of 1-Aryl-1,2-dibromo-2-nitropropanes Promoted by Secondary Amines in Acetonitrile

  摘要：

  Debromination reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes with secondary amines in MeCN have been investigated kinetically. Reactions of erythro-dl-1-aryl-1,2-dibromo-2-nitropropanes with secondary amines in MeCN are stereospecific, producing (E)-1-aryl-2-nitropropenes quantitatively. The rate equation for the reaction is k(obs) = k(2)[R(2)NH] + k(3)[R(2)NH](2), indicating that the reactions proceed by both uncatalyzed and base-catalyzed pathways. The Hammett rho, Bronsted beta, Delta H-double dagger, and Delta S-double dagger values for the k(2) and k(3) processes are 1.22 +/- 0.04 and 1.20 +/- 0.02, 0.77 +/- 0.05 and 1.05 +/- 0.13, 5.6 +/- 0.3 and 1.7 +/- 0.1 kcal/mol, and -49.1 +/- 4.5 and -60.7 +/- 204 eu, respectively. For dehalogenation reactions from vicinal dibromo and bromochloro compounds, the element effect of the leaving group k(Br)/k(Cl) = 7.8 and 25 have been determined for the k(2) and k(3) processes. From these results, the mechanism and the transition-state character of these reactions are assessed.

  DOI：

  10.1021/jo00112a030

文献信息

• Nitroolefins. II. Derivatives of α-Nitroacetophenone
  作者：RICHARD D. CAMPBELL、FREDERICK J. SCHULTZ

  DOI：10.1021/jo01081a013

  日期：1960.11
• Reactions of 1-Aryl-1,2-dibromo-2-nitropropanes with 2-Nitro-2-propyl Anion in DMSO
  作者：Bong Rae Cho、Young Sung Suh、Seung Jae Lee、Eun Jeong Cho

  DOI：10.1021/jo00092a030

  日期：1994.7
• Cho Bong Rue, Suh Young Sung, Lee Seung Jae, Cho Eun Jeong, J. Org. Chem, 59 (1994) N 13, S 3681-3682
  作者：Cho Bong Rue, Suh Young Sung, Lee Seung Jae, Cho Eun Jeong

  DOI：——

  日期：——