2-(羟)-5,6-(亚甲二氧基)-1-茚酮 | 38489-93-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 中文名称: 2-(羟)-5,6-(亚甲二氧基)-1-茚酮
• 中文别名: 5H-茚并[5,6-D]-1,3-二氧杂-5,6(7H)-二酮
• 英文名称: 2-(hydroxyimino)-5,6-(methylenedioxy)-1-indanone
• 英文别名: 6-(Hydroxyimino)-6,7-dihydro-5H-indeno[5,6-d][1,3]dioxol-5-one；(6Z)-6-hydroxyimino-5H-cyclopenta[f][1,3]benzodioxol-7-one
• CAS: 38489-93-9
• 化学式: C₁₀H₇NO₄
• 分子量: 205.17
• InChiKey: MOASMPMCEFUTPH-XFFZJAGNSA-N

物化性质

• 熔点：
  201-204°C (dec.)
• 沸点：
  460.1±45.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  68.1
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  2-(羟)-5,6-(亚甲二氧基)-1-茚酮 在 palladium on activated charcoal 盐酸 、 sodium tetrahydroborate 、 氢气 作用下， 以 乙醇 为溶剂， 生成 5,6-亚甲二氧基-2-氨基茚满
  参考文献：
  名称：

  N-（2-芳基乙基）邻苯二甲酰亚胺的光环合成4-芳基-2-苯并ze庚因-1,5-二酮

  摘要：

  描述了N-（2-芳基乙基）邻苯二甲酰亚胺向4-芳基-2-苯并ze庚因-1,5-二酮的光环化。我们发现芳基环上的供电子取代基的存在（如10a和b所示）对于环化过程的发生是必要的。该方法还允许合成在C 3（11c和d）具有羧酸根基团的2-苯并ze庚二酮，其以非对映异构体的1：1混合物获得。照射邻苯二甲酰亚胺12的结果取决于在取代基的性质，该邻苯二甲酰亚胺在苄基的位置带有一个氧化的取代基。尝试光环化N-（茚满-2-基）邻苯二甲酰亚胺16富电子的邻苯二甲酰亚胺23失效。

  DOI：

  10.1016/s0040-4020(01)87039-3
• 作为产物：
  描述：

  3-[3,4-(亚甲二氧基)苯基]丙酸 在 盐酸 、 氯化亚砜 、 四氯化锡 、 亚硝酸异戊酯 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 4.92h， 生成 2-(羟)-5,6-(亚甲二氧基)-1-茚酮
  参考文献：
  名称：

  Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)

  摘要：

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.

  DOI：

  10.1021/jm00164a037

文献信息

• Nouveaux dérivés de l'indane-1-ol, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent.
  申请人：ADIR ET COMPAGNIE

  公开号：EP0982305A1

  公开（公告）日：2000-03-01

  Composés de formule (I) : dans laquelle : R1, R2, R3, R4 identiques ou différents, représentent un atome d'hydrogène, d'halogène, un groupement alkyle, alkényle, alkynyle, hydroxy, alkoxy, trihalogénoalkyle, ou forment un hétérocycle lorsqu'ils sont pris deux par deux, R5 représente un atome d'hydrogène, un groupement alkyle ou arylalkyle, R6 représente un atome d'hydrogène, d'halogène, un groupement alkyle, hydroxy, alkoxy, ou trihalogénoalkyle, A représente, avec les atomes communs du noyau phényle, un hétérocycle, leurs isomères ainsi que leur sels d'addition à un acide ou à une base pharmaceutiquement acceptable. Médicaments.

  式(I)化合物 其中： R1、R2、R3 和 R4（可以相同或不同）代表氢原子或卤素原子或烷基、烯基、炔基、羟基、烷氧基或三卤烷基，或当它们两个两个相连时形成杂环、 R5 代表氢原子或烷基或芳烷基、 R6 代表氢原子或卤素原子或烷基、羟基、烷氧基或三卤烷基、 A 与苯环上的原子一起代表杂环、 它们的异构体及其与药学上可接受的酸或碱的加成盐。 药用产品。
• US6153625A
  申请人：——

  公开号：US6153625A

  公开（公告）日：2000-11-28
• Synthesis of 4-aryl-2-benzazepine-1,5-diones by photocyclization of N-(2-arylethyl)phthalimides
  作者：M.Rita Paleo、Domingo Domínguez、Luis Castedo

  DOI：10.1016/s0040-4020(01)87039-3

  日期：1994.3

  The photocyclization of N-(2-arylethyl)phthalimides to 4-aryl-2-benzazepine-1,5-diones is described. We found that the presence of electron donating substituents on the aryl ring (as in 10a and b) is necessary for the cyclization process to occur. The procedure also allowed synthesis of 2-benzazepinediones with a carboxylate group at C3 (11c and d) which were obtained as 1:1 mixture of diastereoisomers

  描述了N-（2-芳基乙基）邻苯二甲酰亚胺向4-芳基-2-苯并ze庚因-1,5-二酮的光环化。我们发现芳基环上的供电子取代基的存在（如10a和b所示）对于环化过程的发生是必要的。该方法还允许合成在C 3（11c和d）具有羧酸根基团的2-苯并ze庚二酮，其以非对映异构体的1：1混合物获得。照射邻苯二甲酰亚胺12的结果取决于在取代基的性质，该邻苯二甲酰亚胺在苄基的位置带有一个氧化的取代基。尝试光环化N-（茚满-2-基）邻苯二甲酰亚胺16富电子的邻苯二甲酰亚胺23失效。
• Nonneurotoxic tetralin and indan analogs of 3,4-(methylenedioxy)amphetamine (MDA)
  作者：David E. Nichols、William K. Brewster、Michael P. Johnson、Robert Oberlender、Robert M. Riggs

  DOI：10.1021/jm00164a037

  日期：1990.2

  Four cyclic analogues of the psychoactive phenethylamine derivative 3,4-(methylenedioxy)amphetamine were studied. These congeners, 5,6- and 4,5-(methylenedioxy)-2-aminoindan (3a and 4a, respectively), and 6,7- and 5,6-(methylenedioxy)-2-aminotetralin (3b and 4b, respectively) were tested for stimulus generalization in the two-lever drug-discrimination paradigm. Two groups of rats were trained to discriminate either LSD tartrate (0.08 mg/kg) from saline, or (+/-)-MDMA.HCl (1.75 mg/kg) from saline. In addition, a 2-aminoindan (5a) and 2-aminotetralin (5b) congener of the hallucinogenic amphetamine 1-(2,5-dimethoxy-4- methylphenyl)-2-aminopropane (DOM) were also evaluated. None of the methylenedioxy compounds substituted in LSD-trained rats, while both 3a and 3b fully substituted in MDMA-trained rats. Compounds 4a and 4b did not substitute in MDMA-trained rats. Compounds 5a and 5b did not substitute in MDMA-trained rats, although 5a substituted in LSD-trained rats, but with relatively low potency compared to its open-chain counterpart. In view of the now well-established serotonin neurotoxicity of 3,4-(methylenedioxy)amphetamine and its N-methyl homologue 1, 3a and 3b were evaluated and compared to 1 for similar toxic effects following a single acute dose of 40 mg/kg sc. Sacrifice at 1 week showed that neither 3a nor 3b depressed rat cortical or hippocampal 5-HT or 5-HIAA levels nor were the number of binding sites (Bmax) depressed for [3H]paroxetine. By contrast, and in agreement with other reports, 1 significantly depressed all three indices of neurotoxicity. These results indicate that 3a and 3b have acute behavioral pharmacology similar to 1 but that they lack similar serotonin neurotoxicity.