5-bromofurfural (Z)-oxime | 57784-55-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 5-bromofurfural (Z)-oxime
• 英文别名: (Z)-5-bromofuran-2-carbaldehydeoxime；(NZ)-N-[(5-bromofuran-2-yl)methylidene]hydroxylamine
• CAS: 57784-55-1
• 化学式: C₅H₄BrNO₂
• 分子量: 189.996
• InChiKey: IFWZXDMZYQEEFZ-CLTKARDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromofurfural (Z)-oxime 、 苯甲酰氯 在 吡啶 作用下， 反应 0.17h， 以40%的产率得到[(Z)-(5-bromofuran-2-yl)methylideneamino] benzoate
  参考文献：
  名称：

  Elimination Reactions of (Z)-Thiophene- and (Z)-Furan-2-carbaldehyde O-Benzoyloximes. Effect of β-Aryl Group upon the Nitrile-Forming Anti Transition State

  摘要：

  Elimination reactions of(Z)-thiophene- and (Z)-furan-2-carbaldehyde O-benzoyloximes 1 and 2 with DBU in MeCN have been investigated kinetically. The reactions are second order and exhibit substantial values of Hammett rho and k(H)/k(D) values, and an E2 mechanism is evident. The relative rates of elimination from (Z)-ArCH=NOC(O)C6H4Y are 1/1.1/0.6 for Ar = phenyl/thienyl/furyl, respectively. For reactions of 1 with DBU in MeCN, k(H)/k(D) = 8.2 +/- 0.1, Hammett rho = 1.22 +/- 0.19, beta(1g) = -0.43 +/- 0.01, Delta H-double dagger = 5.9 +/- 0.1 kcal/mol, and Delta S-double dagger = -28.5 +/- 0.3 eu have been determined. The corresponding values for 2 are k(H)/k(D) = 8.8 +/- 0.2, rho = 1.87 +/- 0.05, beta(1g) = -0.55 +/- 0.10, Delta H-double dagger = 6.5 +/- 0.1 kcal/mol, and Delta S-double dagger = -29.0 +/- 1.5 eu. The k(H)/k(D), Hammett rho, and \beta(1g)\ values increase as the beta-aryl group is changed in the order phenyl < thienyl < furyl. The results indicate that the transition state structure for the nitrile-forming elimination changes slightly toward product-like with the change of the beta-aryl group.

  DOI：

  10.1021/jo981169m
• 作为产物：
  描述：

  5-溴-2-呋喃甲醛 在 吡啶 、 盐酸羟胺 作用下， 以 甲醇 为溶剂， 生成 5-bromofurfural (Z)-oxime 、 (E)-5-bromofuran-2-carbaldehydeoxime
  参考文献：
  名称：

  Synthesis and biological evaluation of novel marine-derived indole-based 1,2,4-oxadiazoles derivatives as multifunctional neuroprotective agents

  摘要：

  Phidianidines (1), isolated from the marine opisthobranch mollusk Phidiana militaris, present the first example of natural products possessing an 1,2,4-oxadiazole ring system and show various bioactivities. However, the structure-activity relationship study related to 1 has not been reported yet. As our ongoing effect toward marine-derived potential neuroprotective agents, a series of phidianidine-based derivatives have been synthesized and evaluated for neuroprotective effects against amyloid-beta(25-35) (A beta(25-35))-, hydrogenperoxide (H2O2)-, and oxygen-glucose deprivation (OGD)-induced neurotoxicity in SH-SY5Y cells. The bioassay results indicated that some of analogs, especially 2q and 2r, exhibited good in vitro neuroprotective effects in the above three screening models. The preliminary SAR study indicated that substituent groups introduced to the benzene ring play a crucial role in their bioactivity. In particular, the linear alkoxy group at 4-position favors the neuroprotective activity, while a bulky group could lead the activity decrease or loss. These findings could provide an alternative strategy for the development of novel indole-based 1,2,4-oxadiazole derivatives for the treatment of Alzheimer's disease. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.068