cis-4a,5,6,7,8,8a-hexahydro-4-(p-tolyl)-phthalazin-1(2H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: cis-4a,5,6,7,8,8a-hexahydro-4-(p-tolyl)-phthalazin-1(2H)-one
• 英文别名: (4aR,8aS)-4-(4-methylphenyl)-4a,5,6,7,8,8a-hexahydro-2H-phthalazin-1-one
• 化学式: C₁₅H₁₈N₂O
• 分子量: 242.321
• InChiKey: CAGGMZIQVSXHRG-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  41.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  cis-4a,5,6,7,8,8a-hexahydro-4-(p-tolyl)-phthalazin-1(2H)-one 在 溴 、 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 2-(2-cyanoethyl)-4-(4-methylphenyl)-5,6,7,8-tetrahydro-1(2H)phthalazinone
  参考文献：
  名称：

  Dumitraşcu, Florea; Mitan, Carmen Irena; Drǎghici, Constantin, Revue Roumaine de Chimie, 2002, vol. 47, # 1-2, p. 179 - 183

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-cis-cyclohexanedicarboxylic anhydride 在 三氯化铝 、 一水合肼 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 cis-4a,5,6,7,8,8a-hexahydro-4-(p-tolyl)-phthalazin-1(2H)-one
  参考文献：
  名称：

  Preparation and steric structure of 3(2H)-pyridazinones and 1,2-oxazin-6-ones fused with three- to six-membered saturated carbocycles or norbornane skeleton

  摘要：

  Reactions of cis-2-(4-methylbenzoyl)-cyclopropane- (1) and -cyclobutanecarboxylic acids (2), the stereoisomeric cyclohexyl homologues (3 and 4), and di-endo-3-(4-methylbenzoyl)-bi-cyclo [2.2.1]heptane-2-carboxylic acid (5) with hydrazines yield the cycloalkane-condensed (3(2H)pyridazinones 6-9 and the norbornane di-endo-fused derivatives 10. With hydroxylamine, compounds 1 and 3-5 were transformed to the cycloalkane- and norbornane-condensed 1,2-oxazin-6-ones 11-14. Transformation of 3-5 led to the trans-hexahydroanthrone 17a and its methylene-bridged analogue 24. From the stereoisomeric hexahydro-1(3H)-isobenzofuranones 20 and 21, the partly saturated anthrones were also prepared; the products (16b and 17b) contain the methyl substituent in position 6. On reduction, 16b yield the 2-methyloctahydroanthracene 22. The structures of tl;e compounds were proved by H-1 and C-13 NMR spectroscopy, making use of NOE, DEFT, and CH-COSY techniques.

  DOI：

  10.1007/bf00812708

文献信息

• Copper(II) Chloride as an Efficient Reagent for the Dehydrogenation of Pyridazinone Derivatives
  作者：Ferenc Csende、Zoltán Szabó、Gábor Bernáth、Géza Stájer

  DOI：10.1055/s-1995-4079

  日期：1995.10

  A new procedure is described for the preparation of pyridazinones from 4,5-dihydropyridazinones under mild conditions with CuCl2 in MeCN via halogenation and spontaneous HCl elimination. For the trans-hexahydrophthalazin-8(1H)-one 1B*, the HCl elimination is five times faster than for the corresponding cis isomer 1B.

  描述了一种新方法，通过在温和条件下使用氯化铜（CuCl2）和醋腈（MeCN），从4,5-二氢吡嗪酮制备吡嗪酮，过程包括卤化和自发性盐酸消除。对于反式-六氢邻苯二氮杂酮1B*，盐酸消除的速度是相应顺式异构体1B的五倍。
• Partial Dehydrogenation of Saturated 4-Phenyl-1(2<i>H</i>)-phthalazinone Derivatives by Thionyl Chloride
  作者：Ferenc Csende、Zoltitn Szabó

  DOI：10.1080/00397919308011137

  日期：1993.12

  Abstract cis-4a, 5,6,7,8,8a-Hexahydro-4-phenyl-1(2H)-phthalazinones (2) react with thionyl chloride in benzene to give tetrahydro derivatives (3); the corresponding reaction of methylene bridged derivatives (5) is also described.

  摘要 cis-4a, 5,6,7,8,8a-Hexahydro-4-phenyl-1(2H)-phthalazinones (2) 在苯中与亚硫酰氯反应生成四氢衍生物 (3)；还描述了亚甲基桥连衍生物 (5) 的相应反应。
• Synthesis and structure of cycloalkane- and norbornane-condensed 6-aryl-1,2,4,5-tetrahydropyridazinones
  作者：Ferenc Csende、Anasztárzia Hetényi、Géza Stájer、Ferenc Fülöp

  DOI：10.1002/jhet.5570410217

  日期：2004.3

  The C=N double bond of certain cis- or trans-cycloalkane and diexo- or diendo-norbornane-condensed pyridazinones was reduced with NaBH3CN. The cis- or trans nature of the starting cycloalkane derivatives was always retained in the saturated products, with a high degree of diastereoselectivity: the hydrogen on the new stereocenter and the annelational hydrogen next to the carbonyl always exhibited the

  某些的C = N双键的顺式-或反式-cycloalkane和diexo -或diendo -norbornane缩合哒嗪酮用NaBH减少3 CN。起始环烷烃衍生物的顺式或反式性质始终保留在饱和产物中，并具有高度的非对映选择性：新的立体中心上的氢和羰基旁边的芳基氢始终显示相同的空间取向。立体结构通过核磁共振测量确定，并通过分子建模证实。
• Synthesis and Structural Study of New Saturated Isoindol-1-one Derivatives
  作者：Ferenc Csende、Zolt� Szab�、G斯a St�er

  DOI：10.3987/com-93-6366

  日期：——

  Condensation of 2-p-toluoylcyclohexanecarboxylic acid (1a,b) with primary amines gave the corresponding hexahydroisoindol-1-ones (2a-g) in good yield. The octahydro derivatives (4a-g) were prepared from cis- and trans-hexahydro-1-(2H)-phthalazinone (3a,b) by reduction with zinc-hydrochloric acid via ring contraction. Stereoselective synthesis of cis-N-phenyloctahydroisoindol-1-one (4h) was performed starting from 2b by reduction with magnesium-methanol at room temperature. Configurational assignments of cis and trans isomers were based on H-1- and C-13-nmr spectroscopic studies.