5,5-dimethyl-2-(nitromethylene)hexahydropyrimidine | 1353880-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 5,5-dimethyl-2-(nitromethylene)hexahydropyrimidine
• 英文别名: 5,5-Dimethyl-2-(nitromethylidene)-1,3-diazinane
• CAS: 1353880-58-6
• 化学式: C₇H₁₃N₃O₂
• 分子量: 171.199
• InChiKey: ZNRBQLSNLDLMHS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  69.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-(nitromethylene)hexahydropyrimidine 在 tin(II) chloride dihdyrate 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 0.67h， 生成 1-butyl-5,5-dimethyl-1,4,5,6-tetrahydropyrimidine-2-carbaldehyde oxime
  参考文献：
  名称：

  Nonquaternary Reactivators for Organophosphate-Inhibited Cholinesterases

  摘要：

  A new class of amidine-oxime reactivators of organophosphate (OP)-inhibited cholinesterases (ChE) was synthesized and tested in vitro and in vivo. Compared with 2-PAM, the most promising cyclic amidine-oxime (i.e., 12e) showed comparable or greater reactivation of OP-inactivated AChE and OP-inactivated BChE. To the best of our knowledge, this is the first report of a nonquaternary oxime that has, comparable to 2-PAM, in vitro potency for reactivation of Sarin (GB)-inhibited AChE and BChE. Amidine-oximes were tested in vitro, and reactivation rates for OP-inactivated butyrylcholinesterase (BChE) were greater than those for 2-PAM or MINA. Amidine-oxime reactivation rates for OP-inactivated acetylcholinesterase (AChE) were lower compared to 2-PAM but greater compared with MINA. Amidine-oximes were tested in vivo for protection against the toxicity of nerve agent model compounds. (i.e., a model of Sarin). Post-treatment (i.e., 5 min after OP exposure, i.p,) with amidine oximes 7a-c and 12a, 12c, 12e, 12f, and 15b (145 mu mol/kg, i.p.) protected 100% of the mice challenged with the satin model compound. Even at 25% of the initial dose of amidine-oxime (i.e., a dose of 36 mu mol/kg, i.p.), 7b and 12e protected 100% of the animals challenged with the sarin nerve agent model compound that caused lethality in 6/11 animals without amidine-oxime.

  DOI：

  10.1021/jm201364d
• 作为产物：
  描述：

  二甲基丙二胺 、 1,1-bis(methylthio)-2-nitroethylene 以 乙醇 为溶剂， 生成 5,5-dimethyl-2-(nitromethylene)hexahydropyrimidine
  参考文献：
  名称：

  由α-溴苯乙酮和2-硝基乙烯-1,1-二胺合成1,2,3,5-取代的吡咯

  摘要：

  描述了在120°C的DMF中，在K 2 CO 3存在下，由α-溴苯乙酮和2-硝基乙烯-1,1-二胺简单合成1,2,3,5-取代的吡咯。以高收率和较短的反应时间制备了一系列稠合和非稠合的多取代吡咯。

  DOI：

  10.1016/j.tetlet.2017.05.063

文献信息

• Oxidation Strategy for the Synthesis of Regioisomeric Spiroisobenzofuranopyrroles: Facile Entries to Spiro[isobenzofuran-1,2′-pyrrole] and Spiro[isobenzofuran-1,3′-pyrrole] Derivatives
  作者：Xusheng Shao、Zhong Li、Yefeng Fan、Song Liu、Nanyang Chen、Xiaoyong Xu

  DOI：10.1055/s-0034-1379617

  日期：——

  developed to synthesize two kinds of racemic spiroisobenzofuranopyrrole analogues as regioisomers. In the presence of sodium periodate, cis-indeno[1,2-b]pyrrol-4(1H)-ones were converted into spiro[isobenzofuran-1,2′-pyrrole] derivatives by a two-step process. In addition, oxidative reactions promoted by lead tetraacetate were demonstrated using cis-indeno[2,1-b]pyrrol-8(1H)-ones as substrates, affording

  已经开发了两种实用且有效的方法来合成两种作为区域异构体的外消旋螺异苯并呋喃吡咯类似物。在高碘酸钠存在下，顺式茚并[1,2-b]吡咯-4(1H)-酮通过两步法转化为螺[异苯并呋喃-1,2'-吡咯]衍生物。此外，使用顺式茚并[2,1-b]吡咯-8(1H)-酮作为底物证明了四乙酸铅促进的氧化反应，得到了螺[异苯并呋喃-1,3'-吡咯]衍生物。两种方法的显着特点包括反应条件温和方便，底物范围广，收率中等至极好。根据中间体和产物的比较，提出了可能的机制。
• One-Pot, Three-Component Synthesis of 1,8-Naphthyridine Derivatives from Heterocyclic Ketene Aminals, Malononitrile Dimer, and Aryl Aldehydes
  作者：Xusheng Shao、Zhong Li、Feilong Sun、Fengjuan Zhu

  DOI：10.1055/s-0034-1378823

  日期：——

  was developed for the access of multisubstituted 1,8-naphthyridine derivatives through a one-pot, three-component protocol from heterocyclic ketene animals, malononitrile dimer, and aryl aldehydes in high yields. The 1,8-naphthyridines were formed via Knoevenagel condensation, aza–ene reaction, imine–enamine tautomerization, and intramolecular cyclization.

  开发了一种高效、通用的方法，用于通过单锅、三组分方案从杂环乙烯酮动物、丙二腈二聚体和芳基醛中以高产率获取多取代的 1,8-萘啶衍生物。1,8-萘啶是通过 Knoevenagel 缩合、氮杂-烯反应、亚胺-烯胺互变异构和分子内环化形成的。
• Efficient access to pyrido[1,2-a]pyrimidines and imidazo[1,2-a]pyridines through Knoevenagel reaction/aza–ene addition/intramolecular cyclization
  作者：Abdolali Alizadeh、Atefeh Roosta、Reza Rezaiyehraad

  DOI：10.1007/s13738-019-01845-6

  日期：2020.5

  AbstractAn expeditious metal-free heteroannulation reaction for pyrido[1,2-a]pyrimidines/imidazo[1,2-a]pyridines was developed in green solvent under mild reaction conditions by using three-component reaction of 2-chloroquinoline-3-carbaldehyde, malononitrile and nitroketen aminals, which obtained from the reaction between 1,1-bis(methylthio)-2-nitroethylene and diamines in green solvent under EtOH reflux

  摘要通过2-氯喹啉-3-甲醛的三组分反应，在温和的反应条件下，在绿色溶剂中开发了吡啶[1,2- a ]嘧啶/咪唑并[1,2- a ]吡啶的快速无金属杂环反应。，丙二腈和亚硝基缩醛，它们是由1,1-双（甲硫基）-2-硝基乙烯与二胺在绿色溶剂中于EtOH回流条件下反应制得的。这种一锅法非常简单，分两个步骤进行。本序列可视为具有优良纯度和高收率的对环境有益的过程。 图形摘要通过2-氯喹啉-3-甲醛，丙二腈/一锅三组分反应制备吡啶并[1,2- a ]嘧啶/咪唑并[1,2- a ]吡啶的有效，通用方法描述了在温和且无催化剂的条件下以优异的收率得到的2-氰基乙酸乙酯和亚硝基缩醛。该方案的主要优点是高产率，温和且无催化剂的条件，较短的反应时间和绿色溶剂的应用。
• Application of PEG-400 as a green biodegradable polymeric medium for the catalyst-free synthesis of spiro-dihydropyridines and their use as acetyl and butyrylcholinesterase inhibitors
  作者：Ammar Maryamabadi、Alireza Hasaninejad、Najmeh Nowrouzi、Gholamhossein Mohebbi、Behvar Asghari

  DOI：10.1016/j.bmc.2016.02.019

  日期：2016.3

  A simple, efficient and green approach for the synthesis of spiro-dihydropyridines derivatives by one-pot multi-component reaction of isatin or acenaphthoquinone derivatives (1 equiv) with malononitrile (1 equiv) and N,N′-substituted-2-nitroethene-1,1-diamines (1 equiv) in PEG-400 under catalyst-free conditions is described. This method provides several advantages such as environmental friendliness

  一种简单，有效且绿色的方法，是通过一锅多组分的靛红或萘醌衍生物（1当量）与丙二腈（1当量）和N，N合成螺二氢吡啶衍生物描述了在无催化剂条件下在PEG-400中的'-取代的-2-硝基乙烯-1,1-二胺（1当量）。该方法具有许多优点，例如环境友好，反应时间短和生物重要化合物合成的简单后处理程序。在体外和计算机上研究了合成的化合物抑制乙酰基和丁酰胆碱酯酶的能力。所有化合物均显示出对乙酰和丁酰胆碱酯酶的中等至高水平活性。体外和计算机模拟研究之间具有良好的相关性。
• Highly efficient, one-pot synthesis of novel bis-spirooxindoles with skeletal diversity via sequential multi-component reaction in PEG-400 as a biodegradable solvent
  作者：Ensieh Safari、Ammar Maryamabadi、Alireza Hasaninejad

  DOI：10.1039/c7ra06017c

  日期：——

  A green and efficient one-pot, sequential, multi-component protocol has been developed for the synthesis of some novel symmetrical bis-spirooxindole derivatives from the reaction of isatins, dihalides, malono derivatives and C–H activated carbonyl compounds or ketene aminal derivatives in the presence of potassium carbonate (K2CO3) in polyethylene glycol 400 (PEG-400) as a biodegradable polymeric solvent

  已开发出一种绿色高效的一锅，顺序，多组分方案，该方案用于从靛红，二卤化物，丙二酸衍生物和CH活化的羰基化合物或乙烯酮缩醛衍生物反应中合成一些新颖的对称双螺氧并吲哚衍生物。在室温下，聚乙二醇400（PEG-400）中存在碳酸钾（K 2 CO 3）作为可生物降解的聚合物溶剂。在这项研究中，各种双螺吲哚并吡喃并吡喃，双螺吲哚并苯并吡喃，双螺吲哚并吡啶并嘧啶，双螺吲哚并咪唑并吡啶和双螺吲哚并吡啶。在较短的反应时间内以优异的收率获得了目标化合物，无需进行色谱分离。