methyl 4-[(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl]benzoate | 455321-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: methyl 4-[(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl]benzoate
• 英文别名: Methyl 4-((1,3-dioxoindan-2-ylidene)methyl)benzoate；methyl 4-[(1,3-dioxoinden-2-ylidene)methyl]benzoate
• CAS: 455321-49-0
• 化学式: C₁₈H₁₂O₄
• 分子量: 292.291
• InChiKey: AIXJJLCDYFYXKS-UHFFFAOYSA-N

物化性质

• 沸点：
  505.0±50.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-[(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl]benzoate 、 氨基邻苯二甲胺 在 lead(IV) tetraacetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以81%的产率得到methyl 4-(1-phthalimido-1',3'-dioxo-1',3'-dihydrospiro[aziridine-2,2'-inden]-3-yl)benzoate
  参考文献：
  名称：

  Synthesis and thermal transformations of spiro-fused N-phthalimidoaziridines

  摘要：

  Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3-diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2'-indene]-1',3'-diones in good yields. Heating these aziridines with standard dipolarophiles (N-phenylmaleimide, dimethyl acetylenedicarboxylate, maleate, and fumarate) leads, in most cases, to spiro[inden-2,2'-pyrrole] derivatives as products of 1,3-dipolar cycloaddition of the intermediate azomethine ylides with up to 70-95% yields in the case of N-phenylmaleimide. As is typical for 2-acylaziridines, the competing rearrangement into 2-aryl-4H-indeno[2,1-d][1,3]oxazol-4-ones prevails for less active dipolarophiles. Increasing the electron-releasing properties of the 3-aryl ring allows the observation of the push-pull effect of electron-donating and electron-withdrawing substituents on the ease of the three-membered ring-opening. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.014
• 作为产物：
  描述：

  sodium 2-(ethoxycarbonyl)-1-oxo-1H-inden-3-olate 、 对甲酰基苯甲酸甲酯 在 硫酸 、 溶剂黄146 作用下， 反应 1.08h， 以72%的产率得到methyl 4-[(1,3-dioxo-1,3-dihydro-2H-inden-2-ylidene)methyl]benzoate
  参考文献：
  名称：

  Synthesis and thermal transformations of spiro-fused N-phthalimidoaziridines

  摘要：

  Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3-diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2'-indene]-1',3'-diones in good yields. Heating these aziridines with standard dipolarophiles (N-phenylmaleimide, dimethyl acetylenedicarboxylate, maleate, and fumarate) leads, in most cases, to spiro[inden-2,2'-pyrrole] derivatives as products of 1,3-dipolar cycloaddition of the intermediate azomethine ylides with up to 70-95% yields in the case of N-phenylmaleimide. As is typical for 2-acylaziridines, the competing rearrangement into 2-aryl-4H-indeno[2,1-d][1,3]oxazol-4-ones prevails for less active dipolarophiles. Increasing the electron-releasing properties of the 3-aryl ring allows the observation of the push-pull effect of electron-donating and electron-withdrawing substituents on the ease of the three-membered ring-opening. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.03.014

文献信息

• Three-Component Triple Organocascade Synthesis of Hexahydropyridazine Derivatives via a Sequential Michael/Amination/Cyclization Reaction
  作者：Yan Ming Chen、Kwunmin Chen

  DOI：10.1002/jccs.201500227

  日期：2015.10

  The organocatalytic asymmetric synthesis of hexahydropyridazines were performed through a unique Michael/amination/cyclization reaction. The organocascade reaction proceeded smoothly between 2‐arylidene‐1,3‐indandiones and aldehydes followed by the addition of azodicarboxylates catalyzed by the privileged organocatalyst α,‐α‐L‐diphenylprolinol trimethylsilyl ether (10 mol%) in the presence of a base

  通过独特的迈克尔/胺化/环化反应进行六氢哒嗪的有机催化不对称合成。有机级联反应在2-芳基-1,3-茚满二酮和醛之间平稳进行，然后在碱性添加剂存在下，由特权有机催化剂α，-α-L-二苯基脯氨醇三甲基甲硅烷基醚（10 mol％）催化的偶氮二羧酸酯的添加等3 N（20 MO％）在0℃下。获得了一系列取代的六氢哒嗪，化学收率高至高（55-78％），立体选择性高至合理（51-93％ee和4：1 dr）。
• Phosphine-Catalyzed Internal Redox [4 + 2] Annulation between 1,4-Enynoates and Electron-Deficient Alkenes
  作者：Dongqiu Li、Fang Cheng、Yuhai Tang、Jing Li、Yang Li、Jiao Jiao、Silong Xu

  DOI：10.1021/acs.orglett.1c03206

  日期：2021.12.3

  enynoates are formally oxidized for the annulation while the alkynyl moiety is converted to an alkene. The reaction offers an efficient synthesis of highly functionalized cyclohexenes in moderate to good yields with exclusive regioselectivity and high diastereoselectivity under mild conditions.

  在本文中，我们描述了 1,4-烯炔酸酯与缺电子烯烃的膦催化内部氧化还原 [4 + 2] 环化，其中烯炔酸酯的 γ- 和 φ-C(sp 3 )-H 被正式氧化为环化，而炔基部分转化为烯烃。该反应以中等至良好的产率有效合成高度官能化的环己烯，在温和条件下具有独特的区域选择性和高非对映选择性。
• [3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones towards synthesis of spirocyclopentenes: understanding the mechanism of γ-attack<i>vs.</i>α-attack using DFT studies
  作者：Shaik Anwar、Li-Tzu Lin、V. Srinivasadesikan、Veera Babu Gudise、Kwunmin Chen

  DOI：10.1039/d1ra07165c

  日期：——

  A [3+2] annulation protocol for the construction of functionalized spirocyclopentenes utilizing 1,3-indanedione derived benzylidene-1,3-indanedione and ethyl-2,3-butadienoate at room temperature was developed.

  开发了一种[3+2]环加成协议，利用1,3-茚二酮衍生的苯甲醛基-1,3-茚二酮和2,3-丁二烯酸乙酯在室温下构建官能化螺环戊烯。
• Rauhut-Currier-Initiated Organocascade Reaction: Synthesis of Substituted Dispirocyclohexanes through a [2+2+2] Strategy Between 2-Arylideneindan-1,3-diones and Activated Alkenes
  作者：Yi-Ya Zhang、Ramani Gurubrahamam、Kwunmin Chen

  DOI：10.1002/adsc.201500091

  日期：2015.8.10

  For the synthesis of multisubstituted dispirocyclohexane derivatives, a Rauhut–Currier‐initiated organocascade reaction between 2‐arylideneindan‐1,3‐diones and activated alkenes in the presence of diazabicyclo[2.2.2]octane (DABCO) was demonstrated. The functionalized dispirocyclohexanes with a wide range of substituents were obtained in satisfactory to excellent chemical yields (58–99%) with high chemo‐

  为了合成多取代的二螺环己烷衍生物，在二氮杂双环[2.2.2]辛烷（DABCO）存在下，Rauhut-Currier引发的有机级联反应在2-芳基亚砜-1,3-二酮与活化的烯烃之间进行。具有令人满意的化学收率（58–99％），化学和非对映选择性高（> 95：5 dr）的令人满意的化学收率（58-99％）获得了具有广泛取代基的功能化双螺环己烷。这种有机催化反应通过迈克尔/迈克尔环化反应顺利进行，该反应涉及形成三个新的碳-碳键并同时构建两个全碳螺环季铵盐中心。
• Organocatalytic synthesis of spirocyclohexane indane-1,3-diones via a chiral squaramide-catalyzed Michael/aldol cascade reaction of γ-nitro ketones and 2-arylideneindane-1,3-diones
  作者：Mamatha Amireddy、Kwunmin Chen

  DOI：10.1016/j.tet.2015.08.061

  日期：2015.10

  The paper presents an efficient and stereoselective method for constructing spirocyclohexane indane-1,3-diones. This method is based on a chiral squaramide-catalysed highly diastereo- and enantioselective cascade Michael/aldol reaction between gamma-nitro ketones and 2-arylidene-1,3-indanedione that affords functionalised spirocyclohexane products in high chemical yields with the formation of three stereogenic centres (57-97%; up to >20;1 dr and 86% ee). (C) 2015 Elsevier Ltd. All rights reserved.