9b-hydroxy-1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 9b-hydroxy-1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one
• 英文别名: 9b-hydroxy-2,3-dihydro-1H-pyrrolo[2,1-a]isoindol-5-one
• 化学式: C₁₁H₁₁NO₂
• 分子量: 189.214
• InChiKey: AEEWRCLMCFNCEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  9b-hydroxy-1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one 在 niobium phosphate 作用下， 生成 2,3-dihydro-5H-pyrrolo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  A laboratory-scale annular continuous flow reactor for UV photochemistry using excimer lamps for discrete wavelength excitation and its use in a wavelength study of a photodecarboxlyative cyclisation

  摘要：

  一种新型环形流反应器，用于紫外光化学反应。

  DOI：

  10.1039/c6gc02888h
• 作为产物：
  描述：

  邻苯二甲酰亚胺钠盐 在 水 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 7.33h， 生成 9b-hydroxy-1,2,3,9b-tetrahydro-5H-pyrrolo[2,1-a]isoindol-5-one
  参考文献：
  名称：

  Exploratory Studies of H-Atom Abstraction and Silyl-Transfer Photoreactions of Silylalkyl Ketones and (Silylalkyl)phthalimides

  摘要：

  Exploratory studies have been conducted to probe competitive H-atom abstraction and SET-promoted, silyl-transfer reactions of excited states of silylalkyl ketones and (silylalkyl)phthalimides. Photochemical investigations with the (silylalkyl)phthalimides have demonstrated that typical gamma-H atom abstraction reactions occur upon irradiation in less polar and less silophilic solvents. In contrast, irradiation of these substances in polar-protic-silophilic solvents results in product formation via pathways involving SET-induced desilylation. Photoreactions of silylamido-aryl ketones in either nonsilophilic or silophilic solvents take place almost exclusively by sequential SET silyl-transfer routes to produce azetidine products. Finally, the chemical selectivities of photochemical reactions of silylpropyl-aryl ketones appear to depend on medium polarity and silophilicity. Irradiation of these substrates in less polar-nonsilophilic solvents leads to almost exclusive formation of acetophenone and vinyltrimethylsilane in essentially equal yields by a reaction pathway initiated by gamma-H atom abstraction and 1,4-biradical fragmentation. However, irradiation of these substances in polar-silophilic solvents produces acetophenone and vinyltrimethylsilane in an ca. 1.7:1 ratio reflecting the fact that a silyl-transfer pathway competes with H-atom abstraction under these conditions.

  DOI：

  10.1021/jo9522623

文献信息

• Reductive cyclization of N-iodoalkyl cyclic imides to nitrogen-fused polycyclic amides induced by samarium diiodide
  作者：Deok-Chan Ha、Chang-Soo Yun、Eunsun Yu

  DOI：10.1016/0040-4039(96)00374-7

  日期：1996.4

  SmI2-promoted cyclizations of cyclic imides having 3-iodopropyl or 4-iodobutyl groups on the imide nitrogen have been studied for construction of nitrogen-fused polycyclic amides.

  已经研究了SmI 2促进的在酰亚胺氮上具有3-碘丙基或4-碘丁基的环状酰亚胺的环化，以构建氮稠合的多环酰胺。
• Synthesis of Medium- and Large-Ring Compounds Initiated by Photochemical Decarboxylation of ω-Phthalimidoalkanoates
  作者：Axel G. Griesbeck、Andreas Henz、Wolfgang Kramer、Johann Lex、Frank Nerowski、Michael Oelgemöller、Karl Peters、Eva-Maria Peters

  DOI：10.1002/hlca.19970800324

  日期：1997.5.12

  reaction initiated by intramolecular photo electron transfer is described. Ring sizes available by this method span from 4 (benzazepine-1,5-dione 7) to 26 (cyclodipeptide 26e). Ground-state template formation is proposed as the explanation for the high efficiency of this reaction and for the decrease in reactivity in the presence of organic bases instead of metal carbonates. The crucial step in this

  描述了使用由分子内光电子转移引发的三重态敏化的光脱羧反应，由ω-邻苯二甲酰亚胺基链烷酸酯合成多种羟基内酰胺。通过该方法可获得的环的大小为4（苯并ze庚因-1，5-二酮7）至26（环二肽26e）。提出了基态模板形成作为该反应的高效率和在存在有机碱而不是金属碳酸盐的情况下反应性降低的解释。在该大环化反应中的关键步骤似乎是中间的酮基放射状质子的质子化（方案4）。研究的间隔基是烷基链（C 3 -C 11：5c-h，11a，12），醚（16、18），酯（20、22）和酰胺（26a-f）键。在检测限内，未观察到二聚体（=脱羧偶联）产物，表明分子间光电子转移与分子间光电子转移具有高度优先性。与可比的单线态反应相反，C，C自由基组合步骤以低的立体选择性进行（参见产品11和12）。除了内酯22以外，所有产物在光解条件下都是稳定的。的延长照射22导致螺形成的化合物23，可能通过中间体酰基甜菜碱甜菜碱（方案8）
• Light‐Triggered Transformation of Molecular Baskets into Organic Nanoparticles
  作者：Sarah E. Border、Radoslav Z. Pavlović、Lei Zhiquan、Michael J. Gunther、Han Wang、Honggang Cui、Jovica D. Badjić

  DOI：10.1002/chem.201803693

  日期：2019.1.2

  Discovering novel and functional photoresponsive materials is of interest for improving controlled release of molecules and scavenging toxic compounds for cleaning our environment or designing chemosensors. In this study, we report on the photoinduced decarboxylation of basket 16−, containing three glutamic acids at its rim. This concave compound is, in an aqueous environment (30 mm phosphate buffer at pH 7

  发现新颖的功能性光响应材料对于改善分子的受控释放并清除有毒化合物以清洁环境或设计化学传感器具有重要意义。在这项研究中，我们报告了篮子1 6−的光诱导脱羧，篮子的边缘含有3种谷氨酸。这种凹面化合物在水性环境（pH 7.0的30 m m磷酸盐缓冲液）中是单体（1 H NMR DOSY，DLS），其谷氨酸残基随机排列在其边缘（1 H NMR和MM-OPLS3）。1 6−的辐照（300 nm）导致其α-羧酸盐被完全去除，从而形成两亲2 3−拥有γ-羧酸盐。光化学转化是通过1 H NMR光谱和ESI质谱观察到的与单脱羧和双脱羧产物的连续反应。两亲2 3-是一个预组织分子（MM-OPLS3），在水，骨料成有机纳米颗粒（大约在50-200直径纳米; DLS，TEM和低温TEM），其具有12μ的临界聚集浓度米（ UV / Vis）。由于光触发了单体1 6−向纳米颗粒2 3−的转变，因此我们认为，软材料的刺
• Photochemistry of N-(selenoalkyl)-phthalimides. Formation of N, Se-heterocyclic systems
  作者：Gabriela Oksdath-Mansilla、Adrián A. Heredia、Juan E. Argüello、Alicia B. Peñéñory

  DOI：10.1039/c4pp00452c

  日期：2015.4

  synthesized and their photochemistry was studied at lambda = 300 nm. Steady-state photolysis and laser time-resolved spectroscopy studies confirmed that these reactions proceeded by direct or acetone-sensitized excitation followed by intramolecular electron transfer (ET) between Se atom and the phthalimide moiety. Two main pathways are possible after ET: proton transfer to the ketyl radical anion from the

  合成了多种N-（硒代甲基）烷基邻苯二甲酰亚胺（烷基=-（CH2）n-; n = 2-5，1a，b，d，e）和N-（硒代苄基）丙基邻苯二甲酰亚胺（1c）在λ＝ 300nm下研究了光化学。稳态光解和激光时间分辨光谱研究证实，这些反应是通过直接或丙酮敏化的激发，然后在Se原子和邻苯二甲酰亚胺部分之间进行分子内电子转移（ET）进行的。ET后可能有两个主要途径：质子从CH3Se（+）或-CH2Se（+）-部分转移至酮基自由基阴离子，从而产生相应的双自由基。这些双自由基的崩溃产生具有各自的内或外含硒杂环的环化产物。
• Microphotochemistry: 4,4'-Dimethoxybenzophenone mediated photodecarboxylation reactions involving phthalimides
  作者：Oksana Shvydkiv、Kieran Nolan、Michael Oelgemöller

  DOI：10.3762/bjoc.7.121

  日期：——

  A series of 4,4'-dimethoxybenzophenone mediated intra- and intermolecular photodecarboxylation reactions involving phthalimides have been examined under microflow conditions. Conversion rates, isolated yields and chemoselectivities were compared to analogous reactions in a batch photoreactor. In all cases investigated, the microreactions gave superior results thus proving the superiority of microphotochemistry over conventional technologies.

  一系列4,4'-二甲氧基苯甲酮介导的分子内和分子间光脱羧反应涉及邻苯二甲酰亚胺在微流条件下进行了研究。将转化率、分离收率和化学选择性与批量光反应器中类似反应进行了比较。在所有研究案例中，微反应给出了更好的结果，从而证明了微光化学技术的优越性。