4,4-dimethyl-5-nitropentan-2-one | 35223-73-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4,4-dimethyl-5-nitropentan-2-one
• 英文别名: 5-Nitro-4,4-dimethyl-2-pentanone；4-methyl-4-(nitromethyl)-2-pentanone；5-Nitro-4,4-dimethyl-2-pentanon；4,4-Dimethyl-5-nitro-pentan-2-on；4,4-dimethyl-5-nitro-2-pentanone
• CAS: 35223-73-5
• 化学式: C₇H₁₃NO₃
• mdl: MFCD00034778
• 分子量: 159.185
• InChiKey: HKYNUYYAUZSEKP-UHFFFAOYSA-N

物化性质

• 沸点：
  128-129 °C(Press: 22 Torr)
• 密度：
  1.0546 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  4,4-dimethyl-5-nitropentan-2-one 在 氯化铵 、 锌 作用下， 以49%的产率得到3,4-二氢-3,3,5-三甲基-2H-吡咯 1-氧化物
  参考文献：
  名称：

  Origin of "hetero effect" on nitrogen inversion. Comparison of hydroxylamines and aminoxide anions

  摘要：

  Rate constants for nitrogen inversion in N-benzyl-N-methylhydroxylamine, NN-diethylhydroxylamine, 1-hydroxy-2,2,4,4-tetramethylpyrrolidine, their conjugate bases, and their O-acetyl derivatives in dimethylformamide-d7 were determined based on the H-1 NMR coalescence temperatures. Relative to -OH, the -O- substituent ought to either raise the barrier to inversion owing to stronger lone-pair repulsions or lower the barrier owing to weaker sigma-inductive effects. Yet nearly identical barriers to inversion, DELTA-G double dagger = 12.0-13.3 kcal/mol, are observed for both the hydroxylamine and its conjugate base. Since the observed barrier is little changed upon deprotonation, it is concluded that the pi-repulsive and sigma-inductive contributions must be nearly equal.

  DOI：

  10.1021/jo00025a016
• 作为产物：
  描述：

  1-Nitro-2,4,4-trimethyl-2-pentylnitrat 在 aluminum oxide 、 perhaloalkane 作用下， 以 苯 为溶剂， 生成 4,4-dimethyl-5-nitropentan-2-one
  参考文献：
  名称：

  Thermal rearrangement of .beta.-nitro nitrates to dinitro alcohols

  摘要：

  DOI：

  10.1021/jo00985a008

文献信息

• Pyrazolopyridines and analogs thereof
  申请人：Hays S. David

  公开号：US20060100229A1

  公开（公告）日：2006-05-11

  Pyrazolopyridin-4-amines, pyrazoloquinolin-4-amines, pyrazolonaphthyridin-4-amines, and 6,7,8,9-tetrahydropyrazoloquinolin-4-amines, pharmaceutical compositions containing the compounds, intermediates, methods of making, and methods of use of these compounds as immunomodulators, for inducing or inhibiting cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases, are disclosed.

  吡唑吡啶-4-胺，吡唑喹啉-4-胺，吡唑萘啉-4-胺和6,7,8,9-四氢吡唑喹啉-4-胺，含有这些化合物的药物组合物，中间体，制备方法以及将这些化合物用作免疫调节剂的方法，用于诱导或抑制动物体内细胞因子生物合成，并用于治疗包括病毒性和肿瘤性疾病在内的疾病。
• New synthetic ‘tricks’. Direct conversion of nitro compounds to nitriles
  作者：Fèlix Urpí、Jaume Vilarrasa

  DOI：10.1016/s0040-4039(00)88527-5

  日期：1990.1

  Treatment of primary nitro groups, in CH2Cl2 at 0 °C, with Sn(SPh)4, R3P, and DEAD affords quickly and almost quantitatively the corresponding nitriles, in a combined process of deoxygenation and dehydration. The same result can be obtained, although not so rapidly, using only R3P (2 equiv.) and DEAD (1 equiv.).

  在0°C下，用Sn（SPh）4，R 3 P和DEAD处理CH 2 Cl 2中的伯硝基，可以在脱氧和脱水的组合过程中快速，几乎定量地得到相应的腈。仅使用R 3 P（2当量）和DEAD（1当量）可以获得相同的结果，尽管不是很快。
• Arginine- or Lysine-catalyzed Michael Addition of Nitromethane to α,β-Unsaturated Ketones in Aqueous Media
  作者：Seongsoon Park

  DOI：10.5012/bkcs.2014.35.12.3671

  日期：2014.12.20

  acids can catalyze numerous reactions including the aldol reaction, the Mannich reaction, an α-amination, an α-aminoxylation, the Diels Alder reaction, and an asymmetric conjugate addition. Besides, the salts of proline or modified amino acids exhibit catalytic activities towards Michael addition of nitroalkanes to enones or enals. The products of Michael addition of nitroalkanes provide a variety of key

  由于日益增加的环境问题，“绿色催化剂”正引起更多关注。“绿色催化剂”的要求之一是对生命系统无害且在自然界中可分解。为此，氨基酸是最佳候选者，因为氨基酸是生命系统的天然成分以及可生物降解的材料。最近，人们发现氨基酸可以催化许多反应，包括羟醛反应、曼尼希反应、α-氨基化、α-氨氧基化、Diels Alder 反应和不对称共轭加成。此外，脯氨酸盐或修饰氨基酸的盐对硝基烷烃与烯酮或烯醛的迈克尔加成具有催化活性。硝基烷烃的迈克尔加成产物为各种化合物提供了多种关键构件，例如胺、酮、烷烃和烯烃。作为催化剂的最广泛研究的氨基酸是脯氨酸。脯氨酸催化与羰基化合物反应的反应机理主要涉及亚胺（或亚胺离子）的初始形成，然后转化为烯胺。这种羰基底物的活化过程可以用于其他类型的反应。例如，我们小组最近报道了一种碱性氨基酸可以催化α，β-不饱和酮与过氧化氢的环氧化。筛选了 16 种氨基酸，但只有精氨酸、组氨酸和赖氨酸等三
• α-Nitrohydrazones: versatile intermediates for phosphonate derivatives formation from primary nitro compounds
  作者：L El Kaı̈m、L Grimaud、N.K Jana、C Tirla

  DOI：10.1016/s0040-4039(02)00208-3

  日期：2002.3

  Primary nitro compounds can be easily converted into hydrazonophosphonate derivatives through coupling with aryldiazonium salts followed by an Arbuzov-type reaction with phosphite.

  通过与芳基重氮盐偶合，然后与亚磷酸酯进行Arbuzov型反应，伯硝基化合物很容易转化为肼代膦酸酯衍生物。
• Substituted imidazo ring systems and methods
  申请人：Krepski R. Larry

  公开号：US20070072893A1

  公开（公告）日：2007-03-29

  Imidazo ring systems substituted at the 1-position, pharmaceutical compositions containing the compounds, inter-mediates, methods of making the compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.

  本文揭示了在1位置取代的咪唑环系统，包含这些化合物的制药组合物，中间体，制备这些化合物的方法以及将这些化合物作为免疫调节剂的使用方法，用于诱导动物细胞因子生物合成和治疗包括病毒和肿瘤疾病在内的疾病。