5,6-二甲基-2-甲氧基-3-硝基吡啶 | 441304-11-6

• 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
• 中文名称: 5,6-二甲基-2-甲氧基-3-硝基吡啶
• 英文名称: 5,6-dimethyl-2-methoxy-3-nitropyridine
• 英文别名: 2-methoxy-5,6-dimethyl-3-nitropyridine
• CAS: 441304-11-6
• 化学式: C₈H₁₀N₂O₃
• 分子量: 182.179
• InChiKey: SRJVPJPQVFTOJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,6-二甲基-2-甲氧基-3-硝基吡啶 在 镍 盐酸 、 正丁基锂 、 四甲基乙二胺 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、202.65 kPa 条件下， 反应 6.0h， 生成 3-amino-4-[(3,5-dimethylphenyl)methyl]-5,6-dimethyl-1H-pyridin-2-one
  参考文献：
  名称：

  4-Benzyl and 4-Benzoyl-3-dimethylaminopyridin-2(1H)-ones:  In Vitro Evaluation of New C-3-Amino-Substituted and C-5,6-Alkyl-Substituted Analogues against Clinically Important HIV Mutant Strains

  摘要：

  In a program to optimize the anti-HIV activity of the 4-benzyl and 4-benzoyl-3-dimethylaminopyridinones 9 and 10, lead compounds in a new class of highly potent non-nucleoside type inhibitors of HIV-1 reverse transcriptase, modification of the alkyl substitutents at the C-5 and C-6 positions on the pyridinone ring and of the substitutents on the C-3 amino group has been studied. Of the 17 new 5/6-modified analogues prepared, compounds 31b and 32b substituted at C-5 by an extended nonpolar chain containing an ether function and a C-6 methyl group and compound 35 bearing a C-5 ethyl/C-6 hydroxymethyl substituent pattern were selected on the basis of their in vitro activity against wild-type HIV and the three principle mutant strains, K103N, Y181C, and Y188L. When tested further, it was shown that these molecules, and in particular compound 35, are globally more active than 9, 10, and efavirenz against an additional eight single [L100I, K101E, V106A, E138K, V179E, G190A/S, and F227C] and four double HIV mutant strains [L1001 + K103N, K101E + K103N, K103N + Y181C, and F227L + V106A] which are clinically relevant. Concerning modulation of the N-3 substituent, 36 new analogues were prepared. Of these, the N-methyl-N-(2-methoxyethyl)-substituted compounds 40, 42, and 62, as well as the doubly modified compounds 77a and 77b, were selected from the initial screen and were subsequently shown to be active at sub-micromolar concentrations (IC50'S) against all the other mutant strains except K103N + Y181C and F227L + V106A. Two possible, but distinct, modes of binding of these analogues in RT were suggested from molecular modeling studies. The preferred mode of binding for compound 62, corresponding to the predicted "orientation 1", was revealed in the X-ray crystal structure of the compound 62-RT complex.

  DOI：

  10.1021/jm0408621
• 作为产物：
  描述：

  2-甲基乙酰乙酸乙酯 在 palladium diacetate ammonium hydroxide 、 sodium hydroxide 、 乙醇 、 Bentonite K-10 、 硫酸 、 四丁基氟化铵 、 硝酸 、 sodium 、 三苯基膦 、 silver carbonate 、 三溴氧磷 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， 反应 185.5h， 生成 5,6-二甲基-2-甲氧基-3-硝基吡啶
  参考文献：
  名称：

  基于硅氧烷的溴吡啶衍生物的交叉偶联：链霉菌素和拉维霉素的合成研究。

  摘要：

  制备了高度官能化的4-溴吡啶，并发现它们与芳基三烷氧基硅烷发生了氟化物促进的，Pd催化的交叉偶联，从而产生了空间上要求的联芳基。3-硝基-4-溴吡啶衍生物以高收率与TBAT（四丁基三苯基二氟硅酸铵）偶联，形成联芳基加合物，可作为抗肿瘤抗生素链霉菌素和拉文霉素的总合成的模型系统。[反应：看文字]

  DOI：

  10.1021/ol0357503

文献信息

• Synthesis of the CD-ring of the anticancer agent streptonigrin: studies of aryl–aryl coupling methodologies
  作者：William T. McElroy、Philip DeShong

  DOI：10.1016/j.tet.2006.04.074

  日期：2006.7

  the success of the coupling process. Analogs of the CD biaryl were prepared by coupling of aryl siloxane derivatives (D-ring component) with highly functionalized 4-bromopyridines (C-ring); however, the CD biaryl of the natural product could not be prepared in high yield by siloxane coupling due to the facile formation of reduced pyridine under the coupling conditions. Alternatively, the fully functionalized

  制备了一系列代表抗癌药链霉菌素C环的功能化4-溴吡啶，并评估了它们与链霉菌素D环硅氧烷进行Pd催化交叉偶联的能力。偶联反应通常耐受受阻CD联芳基的制备。然而，双方的电子效应在耦合过程的成功中起着举足轻重的作用。CD联芳基的类似物是通过将芳基硅氧烷衍生物（D-环组分）与高度官能化的4-溴吡啶（C-环）偶联而制得的。然而，由于在偶联条件下容易形成还原的吡啶，因此不能通过硅氧烷偶联以高产率制备天然产物的CD联芳基。或者，用适当官能化的C-环溴化物和D-环芳基硼酸的Suzuki偶联制备链霉菌素的完全官能化的CD联芳基。所描述的方法是高度收敛的并且容易适用于类似物的合成。
• Antipruritics
  申请人：Yasui Kiyoshi

  公开号：US20050101590A1

  公开（公告）日：2005-05-12

  It is intended to provide antipruritics (drugs to control itching, antiitch agents and drugs to stop itching). It is found out that a compound having an agonistic activity to the cannabinoid receptor shows an antipruritics effect.

  这意味着它旨在提供止痒药（用于控制瘙痒的药物，抗瘙痒剂和止痒药）。研究发现，具有激动性作用的大麻素受体的化合物具有止痒效果。
• Pyridone derivatives having affinity for cannabinoid 2-type receptor
  申请人：——

  公开号：US20040082619A1

  公开（公告）日：2004-04-29

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): 1 wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  发现具有与cannabinoid 2型受体结合活性的化合物，其代表式为（I）：1其中R1是由式表示的基团：—Y1—Y2—Y3—Ra其中Y1是单键或类似物；Y2是—C(═O)—NH—或类似物；Y3是可选取代芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选取代烷基或类似物；或R3和R4与相邻原子结合形成环状基团或类似物。
• Pyridone derivatives having a binding activity to the cannabinoid type 2 receptor
  申请人：Tada Yukio

  公开号：US20060052411A1

  公开（公告）日：2006-03-09

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  被发现的化合物具有与cannabinoid type 2 受体结合活性，其化学式为(I)，其中R1是由公式表示的基团：—Y1—Y2—Y3—Ra，其中Y1是单键或类似物；Y2是—C(═O)—NH—或类似物；Y3是可选择取代的芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选择取代的烷基或类似物；或R3和R4与相邻原子一起形成环状基团或类似物。
• Pyridone derivatives having a binding activity to the cannabinoid type 2 recepter
  申请人：TADA Yukio

  公开号：US20100081686A1

  公开（公告）日：2010-04-01

  It was found that the compound having a binding activity to the cannabinoid type 2 receptor represented by the formula (I): wherein R 1 is a group represented by the formula: —Y 1 —Y 2 —Y 3 —R a wherein Y 1 is single bond or the like; Y 2 is —C(═O)—NH— or the like; Y 3 is optionally substituted aryl or the like; R 2 is hydrogen or the like; R 3 is alkyl or the like; R 4 is alkyl or the like; R 5 is optionally substituted alkyl or the like; or R 3 and R 4 taken together with the adjacent atom form cyclic group or the like.

  发现化合物具有与cannabinoid type 2受体结合活性，该化合物的公式为（I）：其中R1是由公式表示的基团：—Y1—Y2—Y3—Ra，其中Y1是单键或类似物；Y2是—C（═O）—NH—或类似物；Y3是可选择的取代芳基或类似物；R2是氢或类似物；R3是烷基或类似物；R4是烷基或类似物；R5是可选择的取代烷基或类似物；或R3和R4与相邻原子结合形成环状基团或类似物。