3,3,5-三甲基-2,4-二氢吡唑 | 3975-85-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 中文名称: 3,3,5-三甲基-2,4-二氢吡唑
• 英文名称: 3,5,5-Trimethylpyrazolin
• 英文别名: 3,5,5-Trimethyl-Δ²-pyrazolin；3,5,5-Trimethyl-2-pyrazolin；3,5,5,-trimethyl-4,5-dihydro-1H-pyrazole；3,5,5-trimethyl Δ²-pyrazoline；3,5,5-trimethylpyrazoline；3,5,5-trimethyl-2-pyrazoline；3,5,5-trimethyl-1,4-dihydropyrazole
• CAS: 3975-85-7
• 化学式: C₆H₁₂N₂
• 分子量: 112.175
• InChiKey: MEVTUZFUVAZEPY-UHFFFAOYSA-N

物化性质

• 沸点：
  160.5 °C(Press: 764 Torr)
• 密度：
  0.8997 g/cm3
• 保留指数：
  910

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,3,5-三甲基-2,4-二氢吡唑 在 lithium perchlorate 作用下， 以 水 、 乙腈 为溶剂， 生成 4-甲基-2-戊酮
  参考文献：
  名称：

  的电化学氧化

  摘要：

  酮-芳基hydr的阳极氧化产生母体酮，而环状则产生重排产物。

  DOI：

  10.1039/c39820001176
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 一水合肼 作用下， 生成 3,3,5-三甲基-2,4-二氢吡唑
  参考文献：
  名称：

  Curtius; Wirsing, Journal fur praktische Chemie (Leipzig 1954), 1894, vol. <2> 50, p. 551

  摘要：

  DOI：

文献信息

• Migration tendencies of functional groups toward sigmatropic rearrangement in 3,3-disubstituted 3H-pyrazoles
  作者：Peter Sciess、Henri Stalder

  DOI：10.1016/s0040-4039(00)92734-5

  日期：——

  3,3-Disubstituted 3H-pyrazoles - aromatise through an intramolecular sigmatropic 1,5-(1,2-) shift of one of the quaternary groups. From a kinetic study of the uncatalysed and of the acid catalysed isomerisation reaction migration tendencies of functional groups in sigmatropic rearrangement toward neutral and toward cationic centers are obtained.

  3,3-二取代的3H-吡唑-通过四元基团之一的分子内σ1,5-（1,2-）转移而芳香化。通过对未催化的和酸催化的异构化反应的动力学研究，获得了在σ重排的官能团向中性中心和向阳离子中心迁移的趋势。
• Complex of titanium halides with acetone azine and its isomer 3, 5, 5-trimethyl-pyrazoline
  作者：Fiona King、David Nicholls

  DOI：10.1016/s0020-1693(00)87413-7

  日期：1978.1

  formed are (TiCl 4 ) 4 (Me 2 C N N CMe 2 ) 3 and TiBr 4 (Me 2 C N N CMe 2 ). Titanium(III) chloride isomerises acetone azine to 3, 5, 5-trimethyl-2-pyrazoline catalytically at 100 °C; titanium(III) is oxidised to titanium(IV) under these conditions or upon long standing at room temperature and the complex [TiCl 3 (Pz′)Pz0 3 ] can be isolated (Pz = 3, 5, 5-trimethyl-2-pyrazoline; Pz′–H).

  摘要在过量的丙酮嗪存在下，氯化钛与溴化物形成配合物TiX 4（Me 2CNNCMe 2）2。当卤化物过量时，形成的产物是（TiCl 4）4（Me 2CNNCMe 2）3和TiBr 4（Me 2CNNCMe 2）。氯化钛（III）在100°C下将丙酮嗪异构化为3，5，5-三甲基-2-吡唑啉; 在这些条件下或长时间在室温下将钛（III）氧化为钛（IV），可以分离出配合物[TiCl 3（Pz'）Pz0 3]（Pz = 3，5，5-三甲基-2-吡唑啉； Pz'–H）。
• Theoretical Analysis and Experimental Study of the Spatial Structure and Isomerism of Acetone Azine and Its Cyclization to 3,5,5-Trimethyl-4,5-dihydro-1H-pyrazole
  作者：V. B. Kobychev、N. M. Vitkovskaya、N. V. Pavlova、E. Yu. Schmidt、B. A. Trofimov

  DOI：10.1007/s10947-005-0054-1

  日期：2004.9

  relative stability of the acyclic isomers of acetone azine (acetone N-(1-methylethylidene) hydrazone (CH3)2C=N-N=C(CH3)2), differing in the position of multiple bonds, and of the cyclic isomer 3,5,5-trimethyl-4,5-dihydro-1H-pyrazole. In the series of structures under study, the latter possesses the greatest thermodynamic stability so that formation of acyclic isomers such as 1-isopropenyl-2-isopropyldiazene

  已进行了一项从头算（RHF/6-31G* 和 MP2/6-31G*）研究，以研究丙酮吖嗪（丙酮 N-（1-甲基亚乙基）腙（CH3）的无环异构体的空间结构和相对稳定性） 2C=NN=C(CH3)2)，在多个键的位置和环状异构体 3,5,5-三甲基-4,5-二氢-1H-吡唑的位置不同。在所研究的一系列结构中，后者具有最大的热力学稳定性，因此从热力学上讲，由丙酮吖嗪形成 1-异丙烯基-2-异丙基二氮烯、丙酮 N-异丙烯基腙和 1,2-二异丙烯基肼等无环异构体在热力学上是不利的。对于每个结构，都发现了稳定的构象，并且估计了分子相对于 NN、CN 和 CC 单键的内部旋转障碍。发现丙酮吖嗪的非共面 goshconformer 具有最大的热力学稳定性。将丙酮吖嗪分子与模型肼、丁二烯和乙烯胺分子进行比较。丙酮吖嗪在构象上是优选的，不仅因为空间因素，还因为氮原子的孤电子对 (LEP) 与相邻的 N=C 多重键的相互作用。
• 1-carbonyl-2-pyrazoline derivatives having herbicidal activity
  申请人：Duphar International Research B.V.

  公开号：US04927452A1

  公开（公告）日：1990-05-22

  The invention relates to a herbicidally active compound of the general ##STR1## wherein R.sub.1, R.sub.2 R.sub.3 and R.sub.4 are equal or different and represent hydrogen atoms, alkyl groups having 1-6 carbon atoms, cycloalkyl groups having 3-6 carbon atoms or alkoxycarbonyl groups having 2-5 carbon atoms; R.sub.5 is a hydrogen atom, an alkyl group or haloalkyl group having 1-8 carbon atoms, a substituted or non-substituted phenyl group, a substituted or non-substituted heterocyclic group, or an alkenyl, alkynyl or alkoxycarbonyl group having 2-5 carbon atoms; and wherein two of the groups R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 together may form a straight or branched alkylene group having 3-5 carbon atoms; Ar is a phenyl group, a phenyl (C.sub.1 -C.sub.4)alkyl group or a heteroaryl group; R.sub.6 is a hydrogen atom or substitutent to Ar, which substituent, in case Ar is a phenyl or phenylalkyl group, is attached to the phenyl group in the ortho position with respect to the sulphonyl or sulphonylalkyl group, and which substituent is selected from the following atoms and groups: a halogen atom; a nitro group; an alkoxycarbonyl group that has 2-8 carbon atoms and is unsubstituted or substituted with one or more hydroxy or C.sub.1 -C.sub.4 alkoxy groups; and an alkyl, hydroxyalkyl, haloalkyl, alkoxy, haloalkoxy, alkylthio, haloalkylthio, alkylsulphonyl and haloalkylsulphonyl group having 1-6 carbon atoms; and R.sub.7 represent a hydrogen atom or one or two halogen atoms or C.sub.1 -C.sub.4 alkyl groups.

  本发明涉及一种具有除草活性的化合物，其一般式为##STR1##其中R.sub.1、R.sub.2、R.sub.3和R.sub.4相等或不同，表示氢原子、具有1-6个碳原子的烷基、具有3-6个碳原子的环烷基或具有2-5个碳原子的烷氧羰基基团；R.sub.5表示氢原子、具有1-8个碳原子的烷基或卤代烷基、取代或未取代的苯基、取代或未取代的杂环基或具有2-5个碳原子的烯基、炔基或烷氧羰基基团；其中R.sub.1、R.sub.2、R.sub.3、R.sub.4和R.sub.5中的两个基团可以共同形成一个直链或分支链的3-5个碳原子的烷基基团；Ar表示苯基、苯基（C.sub.1-C.sub.4）烷基基团或杂环基；R.sub.6表示与Ar相连的氢原子或取代基，该取代基在Ar为苯基或苯基烷基基团时，与磺酰基或磺酰基烷基基团相对应的苯基在邻位上连接，所述取代基选自以下原子和基团：卤原子；硝基基团；具有2-8个碳原子且未取代或取代有一个或多个羟基或C.sub.1-C.sub.4烷氧基团的烷氧羰基基团；以及具有1-6个碳原子的烷基、羟基烷基、卤代烷基、烷氧基、卤代烷氧基、烷硫基、卤代烷硫基、烷基磺酰基和卤代烷基磺酰基基团；R.sub.7表示氢原子或1-2个卤原子或C.sub.1-C.sub.4烷基基团。
• HETEROCYCLIC ASPARTYL PROTEASE INHIBITORS
  申请人：Zhu Zhaoning

  公开号：US20100292203A1

  公开（公告）日：2010-11-18

  Disclosed are compounds of the formula I or a stereoisomer, tautomer, or pharmaceutically acceptable salt or solvate thereof, wherein W is a bond, —C(═S)—, —S(O)—, —S(O) 2 —, —C(═O)—, —O—, —C(R 6 )(R 7 )—, —N(R 5 )— or —C(═N(R 5 ))—; X is —O—, —N(R 5 )— or —C(R 6 )(R 7 )—; provided that when X is —O—, U is not —O—, —S(O)—, —S(O) 2 —, —C(═O)— or —C(═NR 5 )—; U is a bond, —S(O)—, —S(O) 2 —, —C(O)—, —O—, —P(O)(OR 15 )—, —C(═NR 5 )—, —(C(R 6 )(R 7 )) b — or —N(R 5 )—; wherein b is 1 or 2; provided that when W is —S(O)—, —S(O) 2 —, —O—, or —N(R 5 )—, U is not —S(O)—, —S(O) 2 —, —O—, or —N(R 5 )—; provided that when X is —N(R 5 )— and W is —S(O)—, —S(O) 2 —, —O—, or —N(R 5 )—, then U is not a bond; and R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are as defined in the specification; and pharmaceutical compositions comprising the compounds of formula I. Also disclosed is the method of inhibiting aspartyl protease, and in particular, the methods of treating cardiovascular diseases, cognitive and neurodegenerative diseases, and the methods of inhibiting of Human Immunodeficiency Virus, plasmepins, cathepsin D and protozoal enzymes. Also disclosed are methods of treating cognitive or neurodegenerative diseases using the compounds of formula I in combination with a cholinesterase inhibitor or a muscarinic m 1 agonist or m 2 antagonist.

  本发明公开了式I的化合物或其立体异构体、互变异构体、药学上可接受的盐或溶剂，其中W是键，—C(═S)—、—S(O)—、—S(O)2—、—C(═O)—、—O—、—C(R6)(R7)—、—N(R5)—或—C(═N(R5))—；X是—O—、—N(R5)—或—C(R6)(R7)—；但当X为—O—时，U不是—O—、—S(O)—、—S(O)2—、—C(═O)—或—C(═NR5)—；U是键，—S(O)—、—S(O)2—、—C(O)—、—O—、—P(O)(OR15)—、—C(═NR5)—、—(C(R6)(R7))b—或—N(R5)—；其中b为1或2；但当W为—S(O)—、—S(O)2—、—O—或—N(R5)—时，U不是—S(O)—、—S(O)2—、—O—或—N(R5)—；但当X为—N(R5)—且W为—S(O)—、—S(O)2—、—O—或—N(R5)—时，U则不是键；R1、R2、R3、R4、R5、R6和R7如说明书所定义；以及包含式I化合物的药物组合物。本发明还公开了抑制天冬氨酸蛋白酶的方法，特别是治疗心血管疾病、认知和神经退行性疾病的方法，以及抑制人类免疫缺陷病毒、质膜蛋白酶、组织蛋白酶D和原虫酶的方法。本发明还公开了使用式I化合物与胆碱酯酶抑制剂或肌动蛋白M1激动剂或M2拮抗剂相结合治疗认知或神经退行性疾病的方法。