3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine | 74204-92-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine
• 英文别名: 1-phenyl-3-methyltetrahydropyridazine；3-methyl-1-phenyl-1,4,5,6-tetrahydro-pyridazine；3-Methyl-1-phenyl-1,4,5,6-tetrahydro-pyridazin；6-methyl-2-phenyl-4,5-dihydro-3H-pyridazine
• CAS: 74204-92-5
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: AJPYHPVITAVBAY-UHFFFAOYSA-N

物化性质

• 沸点：
  197-198 °C(Press: 6 Torr)
• 密度：
  1.04±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  15.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine 在 PPA 、 Polyphosphoric acid (PPA) 作用下， 反应 0.75h， 以11%的产率得到4-(4-acetyl-1,2,3,4-tetrahydroquinolin-1-yl)butan-2-one
  参考文献：
  名称：

  Benincori, Tiziana; Brenna, Elisabetta; Sannicolo, Franco, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2139 - 2145

  摘要：

  DOI：
• 作为产物：
  描述：

  3-甲基-1-苯基六氢哒嗪 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 3-methyl-1-phenyl-1,4,5,6-tetrahydropyridazine
  参考文献：
  名称：

  Aldehyde dehydrogenase (ALDH) isozymes in the gray short-tailed opossum (Monodelphis domestica): Tissue and subcellular distribution and biochemical genetics of ALDH3

  摘要：

  Polyacrylamide gel isoelectric focusing (PAGE-IEF), cellulose acetate electrophoresis, and histochemical techniques were used to examine the tissue and subcellular distribution, genetics and biochemical properties of aldehyde dehydrogenase (ALDH) isozymes in a didelphid marsupial, the gray short-tail opossum (Monodelphis domestica). At least 14 zones of activity were resolved by PAGE-IEF and divided into five isozyme groups and three ALDH classes, based upon comparisons with properties previously reported for human, baboon, rat, and mouse ALDHs. Opossum liver ALDHs were distributed among cytosol (ALDHs 1 and 5) and large granular (mitochondrial) fractions (ALDHs 2 and 5). Similarly, kidney ALDHs were distributed between the cytosol (ALDH5) and the mitochondrial fractions (ALDHs 2, 4, and 5), whereas a major isozyme (ALDH3), found in high activity in cornea, esophagus, ear pinna, tail, and stomach extracts, was localized predominantly in the cytosol fraction. Phenotypic variants of the latter enzyme were shown to be inherited in a normal Mendelian fashion, with two alleles at a single locus (ALDH3) showing codominant expression. The data provided evidence for genetic identity of corneal, ear pinna, tail, and stomach ALDH3 and supported biochemical evidence from other mammalian species that this enzyme has a dimeric subunit structure.

  DOI：

  10.1007/bf00554209

文献信息

• Synthesis of 1-Aza-6,7-dehydrotropanes via Copper(I)-Catalyzed Coupling of 5-Chloropentan-2-one with Hydrazines and Terminal Alkynes
  作者：Kourosch Tehrani、Wim Van Beek、Karel Weemaes、Wouter Herrebout、Christophe Vande Velde

  DOI：10.1055/s-0037-1611041

  日期：2018.12

  A one-pot, three-component, Cu(I)-catalyzed coupling of primary hydrazines, 5-chloropentan-2-one, and terminal alkynes was developed. The resulting 1-aza-6,7-dehydrotropanes compose a new class of substances while related 1-azatropanes are scarcely described in literature and closely resemble tropane alkaloids. Hydrogenation of the double bond in 1-aza-6,7-dehydrotropanes triggered a rearrangement

  开发了一种一锅、三组分、Cu(I) 催化的伯肼、5-氯戊烷-2-one 和末端炔烃的偶联。由此产生的 1-aza-6,7-dehydrotropanes 构成了一类新的物质，而相关的 1-azatropanes 在文献中几乎没有描述，并且与托烷生物碱非常相似。1-aza-6,7-dehydrotropanes 中双键的氢化引发重排，涉及 [1,3]-氢化物移位，形成环腙。
• Grandberg et al., Zhurnal Obshchei Khimii, 1957, vol. 27, p. 3342; engl. Ausg. S. 3378
  作者：Grandberg et al.

  DOI：——

  日期：——
• The rearrangement of cyclopropylketone arylhydrazones. Synthesis of tryptamines and tetrahydropyridazines
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Yury V. Tomilov

  DOI：10.1016/j.tetlet.2014.09.017

  日期：2014.10

  The cyclopropyliminium rearrangement of cyclopropylketone arylhydrazones may result in two possible products. The first one forms via cyclopropane ring-opening and ring-closure to give six-membered tetrahydropyridazines. The second is formed via ring-closure resulting in a five-membered ring and subsequent Grandberg rearrangement into a tryptamine. The product ratio depends on the nature of the starting hydrazones. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and cytotoxic properties of tryptamine derivatives
  作者：Rinat F. Salikov、Aleksandr Yu. Belyy、Nailya S. Khusnutdinova、Yulia V. Vakhitova、Yury V. Tomilov

  DOI：10.1016/j.bmcl.2015.06.070

  日期：2015.9

  The cyclopropyliminium and subsequent Grandberg rearrangements of cyclopropylketone hydrozones lead to the formation of tryptamines, which were additionally substituted at either the aromatic ring atoms or the amino group. The products were tested for their cytotoxic properties against HepG2, Jurkat and HEK293 cell lines using MTT assay. The highest activity as well as the highest selectivity was found amongst the compounds derived with one benzyl substituent at the amino group. The flow cytometry technique revealed cell-type specificity in terms of the mechanism of viability inhibition. Thus, the compounds were found to induce mainly apoptosis in HEK293 and HepG2 cells, while Jurkat cells displayed late apoptotic and necrotic responses. The apoptosis pathway is most likely to include mitochondrial damage. (C) 2015 Elsevier Ltd. All rights reserved.
• DEEVA N. YU.; KOST A. N., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 2, 228-233
  作者：DEEVA N. YU.、 KOST A. N.

  DOI：——

  日期：——