5-甲基-2-苯基-3a,7a-二氢异吲哚-1,3-二酮 | 75581-74-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: 5-甲基-2-苯基-3a,7a-二氢异吲哚-1,3-二酮
• 英文名称: 4-Methyl-N-phenyl-1,2-dihydrophthalimide
• 英文别名: N-phenyl-4-methyl-1,2-dihydrophthalimide；5-Methyl-2-phenyl-3a,7a-dihydro-1H-isoindole-1,3(2H)-dione；5-methyl-2-phenyl-3a,7a-dihydroisoindole-1,3-dione
• CAS: 75581-74-7
• 化学式: C₁₅H₁₃NO₂
• 分子量: 239.274
• InChiKey: NAPLOJOLAQTGNW-UHFFFAOYSA-N

物化性质

• 熔点：
  120-123 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  463.5±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-苯基马来酰亚胺 、 5-甲基-2-苯基-3a,7a-二氢异吲哚-1,3-二酮 以 苯 为溶剂， 反应 5.0h， 以82%的产率得到9-methyl-2,6-diphenyl-hexahydro-4,8-etheno-pyrrolo[3,4-f]isoindole-1,3,5,7-tetraone
  参考文献：
  名称：

  Shusherina, N. P.; Nesterova, T. L.; Polyakova, O. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1111 - 1115

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苯基马来酰亚胺 在 三乙胺 作用下， 以 苯 为溶剂， 25.0~150.0 ℃ 、53.33 Pa 条件下， 反应 48.33h， 生成 5-甲基-2-苯基-3a,7a-二氢异吲哚-1,3-二酮
  参考文献：
  名称：

  Experiments on the generation of 2-coordinate phosphoryl species by fragmentation of 7-phosphanorbornene and 3-phospholene derivatives

  摘要：

  2,6-Di-tert-butyl-4-methylphenylphosphenite (ArOP=O) was released into the gas phase on heating a neat sample of a 7-phosphanorbornene derivative 6 bearing this aryloxy substituent at 300-degrees-C (0.01 mm). Attempts to prepare 1-adamantyl phosphenite similarly were not successful. Irradiation of 6 in 1,2-dichloroethane at 254 nm failed to cause release of the phosphenite, but when some alcohol was present fragmentation proceeded readily to give the H-phosphonate (ArOPH(O)OR). It was deduced that the species undergoing the fragmentation was a 5-coordinate adduct of 6 and the alcohol. Similar behavior was observed for the other esters and also for a P-phenyl oxide and a P-phenyl sulfide in the 7-phosphanorbornene series, as well as for a 3-phospholene oxide. Isotope exchange experiments with (OH2)-O-18 proved the influence of the irradiation on the formation and fragmentation of the 5-coordinate adduct. Earlier literature reports that 2-coordinate species are released on irradiation of 7-phosphanorbornene and 3-phospholene derivatives therefore need reinterpretation.

  DOI：

  10.1021/jo00075a014

文献信息

• Maleimide cycloadditions by sulfinyldienes: is the sulfur configuration the only controller of the diastereofacial selectivity?
  作者：Maria C. Aversa、Anna Barattucci、Paola Bonaccorsi、Cristina Faggi、Eszter Gacs-Baitz、Assunta Marrocchi、Lucio Minuti、Aldo Taticchi

  DOI：10.1016/j.tet.2005.05.089

  日期：2005.8

  Cyclohexylsulfinyl-3-methyl-1,3-butadienes 5, 6, and 1-[1-(cyclohexylsulfinyl)ethenyl]cyclohexene (7), easily prepared from cyclohexanethiol (1) via transient cyclohexanesulfenic acid (4), were reacted with N-phenylmaleimide under different conditions, at normal and high pressure. The stereochemical outcome of these cycloadditions contributes a better understanding of the relationships among different

  Cyclohexylsulfinyl -3-甲基-1,3-丁二烯5，6，和1- [1-（cyclohexylsulfinyl）乙烯基]环己烯（7），从环己硫醇（容易地制备1）通过瞬时cyclohexanesulfenic酸（4），用与化合物Ñ -苯基马来酰亚胺在不同的条件下，在常压和高压下。这些环加成的立体化学结果有助于更好地理解控制面部非立体定向的不同因素之间的关系。
• Generation of ester and amide derivatives of metaphosphoric acid by photolysis of 2,3-oxaphosphabicyclo[2.2.2]oct-5-ene derivatives
  作者：Louis D. Quin、Béla Pete、Jerzy Szewczyk、Alan N. Hughes

  DOI：10.1016/0040-4039(88)85244-4

  日期：——

  Irradiation at 254 nm of P-NMe2 and P-OEt derivatives of phosphonates where P is incorporated into the 2,3-oxaphosphabicyclo[2.2.2]oct-5-ene framework results in fragmentation of the molecules to release N,N-dimethylamino metaphosphoramidate and ethyl metaphosphate, respectively. Both species polymerize rapidly, but are effectively trapped as phosphate deriva- tives when alcohols are included in the

  在254 nm处照射P-NMe 2和P-OEt膦酸酯衍生物，其中P掺入2,3-氧杂磷双环[2.2.2] oct-5-ene骨架中，导致分子断裂，释放N，N-二甲基氨基偏氨基磷酸酯和偏磷酸乙酯。两种物质都迅速聚合，但是当反应混合物中包含醇时，它们会有效地被捕获为磷酸盐衍生物。
• The mechanism of fragmentation of alkyl α-(oxyimino)benzylphosphonates; use of silica gel as a novel hydroxylic trapping reactant for an intermediate alkyl metaphosphate.
  作者：Louis D. Quin、Xiao-Ping Wu、Eli Breuer、Mahmoud Mahajna

  DOI：10.1016/s0040-4039(00)97042-4

  日期：1990.1

  Silica gel was employed to react with the suspected metaphosphate intermediate of the acid-promoted cleavage of monoalkyl α-(oxyimino)benzylphosphonates. The silica gels displayed CP-MAS 31P NMR signals at about δ −8. A similar value was obtained for silica gel phosphorylated with ethyl metaphosphate from a different source (thermolysis of a P-ethoxy 2,3-oxaphosphabicyclo[2.2.2]octene derivative.

  使用硅胶与α-（氧亚氨基）苄基单膦酸酯的酸促进的裂解的疑似偏磷酸盐中间体反应。硅胶在约δ-8处显示CP-MAS 31 P NMR信号。用另一种来源的偏磷酸乙酯磷酸化的硅胶（对-乙氧基2,3-氧杂磷双环[2.2.2]辛烯衍生物进行热解）获得了相似的值。
• Generation and trapping of O-alkyl metathiophosphates
  作者：Louis D. Quin、Narayan D. Sadanani、Xiao Ping Wu

  DOI：10.1021/ja00199a061

  日期：1989.8

  Synthese d'O-alkyl O-ethyl thiophosphate a partir d'un derive d'etheno oxaphosphorinne et de pentasulfure de phosphore

  合成这些 d'O-烷基 O-乙基硫代磷酸酯 a partir d'un 衍生 d'etheno oxaphosphorinne et de pentasulfure dephosphore
• Mechanistic studies on metaphosphate generation from fragmentation of 2,3-oxaphosphabicyclo[2.2.2]octene derivatives
  作者：Stefan Jankowski、Louis D. Quin

  DOI：10.1021/ja00018a045

  日期：1991.8

  The rates of fragmentation of 3-R-6-methyl-N-phenyl-2,3-oxaphosphabicyclo[2.2.2]oct-5-ene-8,9-dicarboximide 3-oxide, where R = Et2N or EtO, and of the 3-sulfide, where R = EtO, were determined in various solvents and at various temperatures. All reactions were first-order, as they were also when alcohols were present as trapping agents for the released metaphosphoric acid derivatives. From the small solvent effects on rates and activation parameters, it was concluded that the thermal fragmentations occurred by a retrocycloaddition process. This was supported by the similarity in rates for the three substrates, which differ considerably in polarity at phosphorus. The metaphosphates showed selectivity in their reactivity to alcohol mixtures; rates were faster with more nucleophilic alcohols (ethanol vs 2,2,2-trifluoroethanol) and less crowded alcohols (ethanol vs tert-butyl alcohol). A secondary reaction of the released metaphosphate with two of the substrates was detected by kinetics measurements; first-order rate constants were larger when alcohol was not present to remove metaphosphate. Quantum yields in photochemical fragmentations of the substrates were unchanged when alcohols were present; metaphosphates generated in this fashion showed selectivity effects toward alcohols as seen in the thermal fragmentation. No evidence was found for radical intermediates in either process.