1,2,4,8-tetraacetoxy-naphthalene | 24291-21-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,2,4,8-tetraacetoxy-naphthalene
• 英文别名: Naphthalintetrayl-(1.2.4.8)-tetraacetat；1,2,4,8-Tetraacetoxy-naphthalin；(5,7,8-Triacetyloxynaphthalen-1-yl) acetate
• CAS: 24291-21-2
• 化学式: C₁₈H₁₆O₈
• 分子量: 360.32
• InChiKey: OFRADTYNMFQVST-UHFFFAOYSA-N

物化性质

• 熔点：
  167-168 °C
• 沸点：
  512.1±50.0 °C(Predicted)
• 密度：
  1.314±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,2,4,8-tetraacetoxy-naphthalene 在 氢氧化钾 作用下， 生成 4,8-dihydroxynaphthalene-1,2-dione
  参考文献：
  名称：

  Mentally disordered parricide and stranger killers admitted to high-security care. 1: A descriptive comparison

  摘要：

  Parricide is an uncommon crime, so that many of the descriptive studies suffer from methodological shortcomings of small sample sizes and a non-representative ascertainment. We describe a consecutive series of mentally disordered offenders convicted of parricide who were admitted to high-security care and we compare their index characteristics with a group convicted of killing one or more strangers. The main findings were that the parricides were more likely to suffer from schizophrenia but less likely to have had a disrupted childhood and criminal history, as compared with those who had killed a stranger. Those in the parricide group had made a previous attack on their victim in 40% of cases. Overall, the study confirmed some of the differences that one might expect between these two groups of homicides, which had entirely different relationships to their victims.

  DOI：

  10.1080/09585180122057
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 生成 1,2,4,8-tetraacetoxy-naphthalene
  参考文献：
  名称：

  The chemistry of Quinones. I. Directive effects in the Substitution of Naphthoquinones

  摘要：

  二甲胺与 与 5-甲氧基-1,4-萘醌的反应会产生近似等量的两种可能的取代产物。 与 6-甲基-1,4-萘醌反应，然后进行酸水解，可生成 2-羟基-6-甲基-1,4-萘醌。 2-hydroxy-6-methyl-l,4-naphtho-quinone 是主要产物。 产物。对 5-甲基-1,4-萘醌进行类似处理后，主要产物为 3-羟基-5-甲基-l,4-萘醌。异构体 2-羟基-5-甲基-1,4-萘醌是主要产物。 甲基-1,4-萘醌的异构体。其产物为 乙酸酐与丁二酮的 Thiele-Winter 加成产物被证明是两种可能异构体的混合物。 但真正的 1，3，4，5-四乙酰氧基萘是由 3，5-二乙酰氧基萘制备的。 但真正的 1,3,4,5-四乙酰氧基萘是由 3,5-二羟基-1,4-萘醌制备的。乙酸酐与 反应生成三种化合物，混合物的成分取决于接触的时间。 取决于接触的时间。Juglone 和 plumbagin 在 6 位被选择性溴化。 6 位溴化，并制备出了这些醌类化合物的某些其他卤素衍生物。 醌的某些其他卤素衍生物。3-氯-5-羟基-2-甲基-1,4-萘醌的制备方法 提供了一条从 plumbagin 中获得 droserone 的新途径。

  DOI：

  10.1071/ch9530038

文献信息

• Synthesis of juglone derivatives
  作者：H. Singh、T.L. Folk、P.J. Scheuer

  DOI：10.1016/0040-4020(69)80052-9

  日期：——

  A number of hydroxyjuglones were prepared by the Thiele-Winter reaction onjuglone derivatives and by hydroxylation with ethanol-hydrochloric acid: 2-hydroxy, 3-hydroxy, 2,7-dihydroxy, 3,7-di-hydroxy, 6-acetyl-2-hydroxy, and 6-acetyl-3-hydroxyjuglone. By reductive acetylation of hydroxyjuglones, followed by Fries rearrangement and oxidative hydrolysis several acetyljuglones, and from them ethyljuglones

  通过Thiele-Winter反应onjuglone衍生物并用乙醇-盐酸进行羟基化反应，制得了许多羟基juglones：2-羟基，3-羟基，2,7-二羟基，3,7-二羟基，6-乙酰基-2 -羟基和6-乙酰基-3-羟基juglone。通过对羟基juglones进行还原性乙酰化，然后进行弗里斯重排和氧化水解，从而合成了几个乙酰juglones，并通过硼氢化钠还原从中合成了乙基juglones：3-乙酰基-2-羟基，6-乙酰基-2,3-二羟基，6-乙酰基- 2,7-二羟基和6-乙酰基-2,3,7-三羟基胡胶。先前已从海胆棘中分离出几种新合成的化合物。
• Triflic acid an efficient catalyst for the Thiele-Winter reaction
  作者：Didier Villemin、Nathalie Bar、Mohamed Hammadi

  DOI：10.1016/s0040-4039(97)01049-6

  日期：1997.7

  Triflic acid is a convenient and non hazardous acid for the Thiele-Winter reaction of quinones. The synthetic scope of the Thiele-Winter reaction was increased by the use of triflic acid. (C) 1997 Elsevier Science Ltd.
• STUDIES IN THE JUGLONE SERIES. II. HYDROXY AND HYDROXYHALOGENO DERIVATIVES
  作者：R. H. THOMSON

  DOI：10.1021/jo01164a015

  日期：1948.11
• Mentally disordered parricide and stranger killers admitted to high-security care. 1: A descriptive comparison
  作者：Helen Baxter、Conor Duggan、Emmet Larkin、Christopher Cordess、Kim Page

  DOI：10.1080/09585180122057

  日期：2001.1

  Parricide is an uncommon crime, so that many of the descriptive studies suffer from methodological shortcomings of small sample sizes and a non-representative ascertainment. We describe a consecutive series of mentally disordered offenders convicted of parricide who were admitted to high-security care and we compare their index characteristics with a group convicted of killing one or more strangers. The main findings were that the parricides were more likely to suffer from schizophrenia but less likely to have had a disrupted childhood and criminal history, as compared with those who had killed a stranger. Those in the parricide group had made a previous attack on their victim in 40% of cases. Overall, the study confirmed some of the differences that one might expect between these two groups of homicides, which had entirely different relationships to their victims.
• The chemistry of Quinones. I. Directive effects in the Substitution of Naphthoquinones
  作者：RG Cooke、H Dowd、W Segal

  DOI：10.1071/ch9530038

  日期：——

  The reaction of dimethylamine with 5-methoxy-1,4-naphthoquinone gives approximately equal amounts of the two possible substitution products and with 6-methyl-1,4-naphthoquinone followed by acid hydrolysis 2-hydroxy-6-methyl-l,4-naphtho-quinone is the principal product. Similar treatment of 5-methyl-1,4-naphthoquinone gives mostly 3-hydroxy-5-methyl-l,4-naphtlioquinone. The isomer, 2-hydroxy-5- methyl-1,4-naphthoquinone, has been prepared by another method. The product of Thiele-Winter addition of acetic anhydride to juglone is shown to be a mixture of the two possible isomers, but authentic 1,3,4,5-tetra-acetoxynaphthalene has been prepared from 3,5-dihydroxy-1,4-naphthoquinone. The reaction of acetic anhydride with plumbagin gives three compounds, the composition of the mixture depending on the time of contact. Juglone and plumbagin have been selectively brominated in the 6-position and certain other halogen derivatives of these quinones have been prepared. The preparation of 3-chloro-5-hydroxy-2-methyl-1,4-naphthoquinone provides a new route by which droserone may be obtained from plumbagin.

  二甲胺与 与 5-甲氧基-1,4-萘醌的反应会产生近似等量的两种可能的取代产物。 与 6-甲基-1,4-萘醌反应，然后进行酸水解，可生成 2-羟基-6-甲基-1,4-萘醌。 2-hydroxy-6-methyl-l,4-naphtho-quinone 是主要产物。 产物。对 5-甲基-1,4-萘醌进行类似处理后，主要产物为 3-羟基-5-甲基-l,4-萘醌。异构体 2-羟基-5-甲基-1,4-萘醌是主要产物。 甲基-1,4-萘醌的异构体。其产物为 乙酸酐与丁二酮的 Thiele-Winter 加成产物被证明是两种可能异构体的混合物。 但真正的 1，3，4，5-四乙酰氧基萘是由 3，5-二乙酰氧基萘制备的。 但真正的 1,3,4,5-四乙酰氧基萘是由 3,5-二羟基-1,4-萘醌制备的。乙酸酐与 反应生成三种化合物，混合物的成分取决于接触的时间。 取决于接触的时间。Juglone 和 plumbagin 在 6 位被选择性溴化。 6 位溴化，并制备出了这些醌类化合物的某些其他卤素衍生物。 醌的某些其他卤素衍生物。3-氯-5-羟基-2-甲基-1,4-萘醌的制备方法 提供了一条从 plumbagin 中获得 droserone 的新途径。