4-nitro-1,3-diphenyl-pentan-1-one | 6277-76-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 4-nitro-1,3-diphenyl-pentan-1-one
• 英文别名: 4-nitro-1,3-diphenyl-1-pentanone；4-Nitro-1,3-diphenyl-pentan-1-on；Phenyl-(γ-nitro-β-phenyl-butyl)-keton；γ-Nitro-β-phenyl-valerophenon；4-nitro-1,3-diphenylpentan-1-one
• CAS: 6277-76-5
• 化学式: C₁₇H₁₇NO₃
• 分子量: 283.327
• InChiKey: ZISZMLQGFYEQMF-UHFFFAOYSA-N

物化性质

• 熔点：
  100 °C
• 沸点：
  456.1±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-nitro-1,3-diphenyl-pentan-1-one 在 氢氧化钾 、 溴 作用下， 以 氯仿 为溶剂， 反应 0.25h， 生成 (3aR*,3bS*,8aS*)-3a,8a-Dihydro-6,8a-dimethyl-2,3a,3b,5-tetraphenyl-3H-dipyrrol<1,2-b:3',2'-d>isoxazole-3,4(3bH)-dione-1-Oxide
  参考文献：
  名称：

  Self-condensation of 3H-pyrrol-3-one 1-oxides

  摘要：

  DOI：

  10.1021/jo00189a041
• 作为产物：
  描述：

  2-(4-nitro-1,3-diphenylpentylidene)hydrazine-1-carboxamide 在 氯化亚砜 作用下， 生成 4-nitro-1,3-diphenyl-pentan-1-one
  参考文献：
  名称：

  Saravanan; Amuthavalli; Muthusubramanian, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2009, vol. 48, # 8, p. 1144 - 1147

  摘要：

  DOI：

文献信息

• Solvent-Free Synthesis of <b>γ</b>-Nitroketones and <b>γ</b>-Nitroesters Promoted by the Ionic Liquid/K₂CO₃ Catalytic System
  作者：Sergey Zlotin、Andrey Bogolyubov、Galina Kryshtal、Galina Zhdankina、Marina Struchkova、Vladimir Tartakovsky

  DOI：10.1055/s-2006-950306

  日期：2006.11

  A convenient solvent-free synthesis of γ-nitroketones and γ-nitroesters based on the reaction of nitroalkanes with α,β-unsaturated carbonyl compounds in the ultrasonically activated hete­rogeneous catalytic system 1-butyl-3-methylimidazolium tetra­-fluoroborate ([bmim][BF4])/K2CO3 has been developed. The system retained its catalytic activity over three reaction cycles.

  基于1-丁基-3-甲基咪唑四氟硼酸盐（[bmim][BF4]）/K2CO3在超声激活的非均相催化体系中，通过硝基烷与α,β-不饱和羰基化合物的反应，已开发出一种方便的无溶剂合成γ-硝基酮和γ-硝基酯的方法。该系统在三次反应循环中保持了其催化活性。
• Henry Reaction and 1,4-Addition of Nitroalkanes to α,β-Unsaturated Carbonyl Compounds under the Influence of MS 4 Å in DMSO
  作者：Takeshi Oriyama、Masaru Aoyagi、Katsuyuki Iwanami

  DOI：10.1246/cl.2007.612

  日期：2007.5.5

  In the presence of MS 4 Å in DMSO (dimethyl sulfoxide), Henry reaction with various carbonyl compounds and nitroalkanes proceeded smoothly to give the corresponding β-nitroalcohol without a base catalyst. Moreover, 1,4-additon of nitroalkane to α,β-unsaturated ketones was also performed in DMSO.

  在 DMSO（二甲基亚砜）中加入 MS 4 Å 的情况下，各种羰基化合物与硝基烷烃的 Henry 反应顺利进行，无需碱催化剂即可得到相应的 β-硝基醇。此外，硝基烷烃对 α,β-不饱和酮的 1,4-加成反应也在 DMSO 中得以实现。
• Synthesis of 1,4-diketones by fluoride-catalysed Michael addition and supported permanganate oxidation
  作者：James H. Clark、David G. Cork

  DOI：10.1039/c39820000635

  日期：——

  A wide variety of 1,4-diketones may be prepared from simple starting materials by using fluoride ion-catalysed Michael additions and silica gel-supported permanganate-promoted Nef transformations.

  通过使用氟化物离子催化的迈克尔加成反应和硅胶负载的高锰酸盐促进的Nef转化，可以从简单的起始原料制备各种1,4-二酮。
• Synthesis of multisubstituted 1H-pyrrole: selenium-catalyzed reaction of γ-nitro substituted carbonyl compounds and carbon monoxide
  作者：Rui Umeda、Tsukasa Mashino、Yutaka Nishiyama

  DOI：10.1016/j.tet.2014.04.061

  日期：2014.7

  The novel and efficient selenium-catalyzed reductive N-heterocyclization of γ-nitro substituted carbonyl compounds with carbon monoxide has been developed. Various multisubstituted 1H-pyrroles can be easily prepared by this protocol. The one-pot synthesis of ethyl 1H-pyrrole-3-carboxylate derivatives was also successfully attained by the selenium-catalyzed reaction of β-ketoester, vinyl nitro compounds and

  已经开发出新颖和有效的硒催化一氧化碳对γ-硝基取代的羰基化合物进行硒催化的还原性N-杂环化。通过该方案可以容易地制备各种多取代的1 H-吡咯。通过硒催化β-酮酸酯，乙烯基硝基化合物和一氧化碳的反应，也成功地完成了1 H-吡咯-3-羧酸乙酯衍生物的一锅法合成。
• The synthesis and chemistry of azolenines.1
  作者：Pak-Kan Chiu、Michael P. Sammes

  DOI：10.1016/s0040-4020(01)85983-4

  日期：1988.1

  Treatment of 1,4-diketones with liquid ammonia gives high yields of isolable 2-hydroxy-3,4-dihydro-2H-pyrrole intermediates. These intermediates, which do not appear to have been observed previously in the Paal-Knorr synthesis with ammonia, have been fully characterized by i.r. and 1H and 13C n.m.r. spectroscopy; in most cases they decompose quantitatively into 1H-pyrroles on standing. The intermediate from

  用液氨处理1，4-二酮可获得高产率的可分离的2-羟基-3，4-二氢-2 H-吡咯中间体。这些中间体，以前似乎没有在Paal-Knorr与氨的合成中观察到，已通过ir，1 H和13 C nmr光谱进行了全面表征。在大多数情况下，它们在站立时会定量分解为1 H-吡咯。来自己烷-2，4-二酮的中间体也可以使用浓氨水制备。