3-nitro-1,4-diphenyl-2-butanol | 151830-79-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-nitro-1,4-diphenyl-2-butanol
• 英文别名: 3-nitro-1,4-diphenylbutan-2-ol
• CAS: 151830-79-4
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: AWAVEGGZOTYWEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.37
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-nitro-1,4-diphenyl-2-butanol 在 chromium(VI) oxide 、 platinum(IV) oxide 、 sodium hydroxide 、 硫酸 、 氢气 作用下， 以 乙醇 、 丙酮 为溶剂， 90.0 ℃ 、344.73 kPa 条件下， 反应 5.0h， 生成 2-amino-4,5-bis(phenylmethyl)imidazole
  参考文献：
  名称：

  Synthesis and LTB4 receptor antagonist activities of the naturally occurring LTB4 receptor antagonist leucettamine A and related analogs

  摘要：

  The isolation and structure determination of the naturally occurring LTB4 receptor antagonist Leucettamine A (1) was recently reported.1 Herein we describe the synthesis of this natural product, the preparation of several analogues, and their effectiveness as antagonists of [H-3]LTB4 binding to intact human U-937 cells. Total synthesis of Leucettamine A 1) is achieved by a convergent route which takes advantage of the elements of symmetry within the molecule. Syntheses of analogues of 1, which lacked the same degree of symmetry, are achieved by a different approach starting from alpha-amino acids. The natural product 1 inhibits [H-3]LTB4 binding to its receptors on intact human U-937 cells with a K(i) = 3.5 +/- 0. 8 muM and is devoid of measurable agonist activity at the concentrations tested. 2-Amino imidazole analogues of 1 lacking the dioxolane groups were prepared. Generally these are significantly less potent than 1. However, one (26), designed on the basis of a putative structural overlay with LTB4, demonstrated potency comparable to that of the natural product (K(i) = 2.4 +/- 0.2 muM).

  DOI：

  10.1021/jm00074a014
• 作为产物：
  描述：

  2-苯乙胺 在 potassium fluoride on basic alumina 、 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 反应 8.0h， 生成 3-nitro-1,4-diphenyl-2-butanol
  参考文献：
  名称：

  Synthesis and LTB4 receptor antagonist activities of the naturally occurring LTB4 receptor antagonist leucettamine A and related analogs

  摘要：

  The isolation and structure determination of the naturally occurring LTB4 receptor antagonist Leucettamine A (1) was recently reported.1 Herein we describe the synthesis of this natural product, the preparation of several analogues, and their effectiveness as antagonists of [H-3]LTB4 binding to intact human U-937 cells. Total synthesis of Leucettamine A 1) is achieved by a convergent route which takes advantage of the elements of symmetry within the molecule. Syntheses of analogues of 1, which lacked the same degree of symmetry, are achieved by a different approach starting from alpha-amino acids. The natural product 1 inhibits [H-3]LTB4 binding to its receptors on intact human U-937 cells with a K(i) = 3.5 +/- 0. 8 muM and is devoid of measurable agonist activity at the concentrations tested. 2-Amino imidazole analogues of 1 lacking the dioxolane groups were prepared. Generally these are significantly less potent than 1. However, one (26), designed on the basis of a putative structural overlay with LTB4, demonstrated potency comparable to that of the natural product (K(i) = 2.4 +/- 0.2 muM).

  DOI：

  10.1021/jm00074a014

文献信息

• Synthesis of Nitro Alcohols by Riboflavin Promoted Tandem Nef‐Henry Reactions on Nitroalkanes
  作者：Gabriele Lupidi、Alessandro Palmieri、Marino Petrini

  DOI：10.1002/adsc.202001344

  日期：2021.2.2

  We disclose a unprecedented riboflavin promoted Nef reaction of primary nitroalkanes coupled with a nitroaldol reaction. This tandem process allows the synthesis of functionalized nitro alcohols under mild reaction conditions. Secondary nitroalkanes fail to give the expected nitroaldol products although they are consumed under the reaction conditions.

  我们公开了空前的核黄素促进伯硝基烷烃的Nef反应与硝基醛醇反应的结合。该串联过程允许在温和的反应条件下合成官能化的硝基醇。尽管仲硝基烷烃在反应条件下被消耗，但它们不能提供预期的硝基醛醇产物。