2-(2-nitrobenzylidene)indan-1,3-dione | 15875-61-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(2-nitrobenzylidene)indan-1,3-dione
• 英文别名: 2-(2-nitrobenzylidene)-1H-indene-1,3(2H)-dione；2-(2-nitrobenzylidene)-1,3-indandione；2-(2-nitro-benzylidene)-indan-1,3-dione；1.3-Dioxo-2-(2-nitro-benzyliden)-hydrinden；2-(2-Nitro-benzyliden)-indan-1,3-dion；2-(2-Nitro-benzyliden)-indandion-(1,3)；2-[(2-nitrophenyl)methylene]-1H-indene-1,3(2H)-dione；2-[(2-nitrophenyl)methylidene]indene-1,3-dione
• CAS: 15875-61-3
• 化学式: C₁₆H₉NO₄
• mdl: MFCD00170369
• 分子量: 279.252
• InChiKey: LNZCOFHMUCVBOR-UHFFFAOYSA-N

物化性质

• 熔点：
  182-183 °C
• 沸点：
  513.7±50.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-nitrobenzylidene)indan-1,3-dione 在 盐酸 、 锌 作用下， 以 溶剂黄146 为溶剂， 反应 3.0h， 以45%的产率得到11H-茚并[1,2-B]喹啉-11-酮
  参考文献：
  名称：

  Etmann, H.A.; Sofan, M.A.; Metwally, M.A., Bollettino Chimico Farmaceutico, 1995, vol. 134, # 5, p. 249 - 253

  摘要：

  DOI：
• 作为产物：
  描述：

  碘正离子,苯基-,3,4-二氢-1,3,4-三羰基-2(1H)-萘自由基负离子 、 邻硝基苯甲醛 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 1.33h， 以57%的产率得到2-(2-nitrobenzylidene)indan-1,3-dione
  参考文献：
  名称：

  Styryl and functionalized aryl derivatives of lawsone through metal-free cross-coupling of its BF3-activated phenyliodonium ylide with cinnamaldehydes and arylaldehydes

  摘要：

  Phenyliodonium ylide of lawsone activated with BF3 center dot Et2O reacts with cinnamaldehydes to afford 2-hydroxy-3-styryl-1,4-naphthoquinones in good to excellent yields and relatively high level of stereospecificity through deformylation of the aldehydes. The product yield is diminished with a methoxy substituted cinnamaldehyde and becomes zero with a dimethoxy substituted substrate giving rise to another product, 2-hydroxy-3-aryl-1,4-naphthoquinone. The reaction of the same ylide with salicylic aldehydes forms 2-hydroxy-3-(2-hydroxyary1)-1,4-naphthoquinones and/or benzo[d]naphtha[2,1-b]furano-5,6-diones, depending on the reaction conditions applied. Plausible reaction mechanisms explaining the formation of these products are proposed. The products showed potent antioxidant activity and inhibited lipoxygenase. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.037

文献信息

• Asymmetric Organocatalytic One-Pot, Two-Step Sequential Process to Synthesize Chiral Acetal-Containing Polycyclic Derivatives from Cyclic Hemiacetals and Enones
  作者：Chao Liu、Yan-Kai Liu

  DOI：10.1021/acs.joc.7b01915

  日期：2017.10.6

  synthesize biologically and synthetically important chiral acetal-containing polycyclic derivatives. This novel protocol had been proved to proceed via Michael-lactolization-oxocarbenium ion ring-closing sequence, which was initiated by a key reactive enamine intermediate and interrupted the previously established reaction pathway of two different enones used in this work, and generated the corresponding

  我们已经开发了一种有效的一锅，两步顺序方法，可以合成生物学上和合成上重要的手性含缩醛的多环衍生物。事实证明，该新方案可通过迈克尔-乳化-氧碳鎓离子闭环序列进行，该过程由关键的反应性烯胺中间体引发，中断了先前在该工作中使用的两种不同烯酮的反应路径，并生成了相应的环加合物具有出色的立体选择性，最多可容纳七个连续的立体中心。手性和外消旋起始环状半缩醛在该策略中均能很好地发挥作用。还证明了所得多环产物的合成应用。
• Aqueous extract of Balanites roxburghii fruit: a green dispersant for C–C bond formation
  作者：Madhuri Barge、Rajashri Salunkhe

  DOI：10.1039/c4ra04387a

  日期：——

  A natural dispersant exhibiting recyclable buffer property is obtained from aqueous extract ofBalanites roxburghiifruit and used as a highly efficient catalytic medium for C–C bond constructionviaKnoevenagel condensation and tandem Knoevenagel–Michael reaction.

  从Balanites roxburghii果实的水提取物中获得一种具有可回收缓冲特性的天然分散剂，并将其用作高效的催化介质，用于通过Knoevenagel缩合和串联Knoevenagel-Michael反应构建C-C键。
• Clean synthesis of 2-arylideneindan-1,3-diones in water
  作者：Peng Hui Yang、Qun Zheng Zhang、Wei Sun

  DOI：10.1007/s11164-011-0442-4

  日期：2012.3

  A high-yield synthesis of 2-arylideneindan-1,3-diones in water was achieved by the Knoevenagel condensation of indan-1,3-dione with aromatic aldehydes at ambient temperature avoiding the addition of any catalyst. The procedure is simple, efficient, as well as environmentally friendly.

  在常温下，通过与芳香醛的Knoevenagel缩合反应，在水中高产合成了2-芳基亚甲基茚-1,3-二酮，且无需添加任何催化剂。该方法简单、高效，并且对环境友好。
• Efficient syntheses of novel indeno[1,2-b]chromenone derivatives via hetero-Diels-Alder reactions of 2-(arylmethylene)-1H-indene-1,3(2H)-diones with enaminones
  作者：Kalawati Meena、Sudesh Kumari、Jitender M. Khurana、Amita Malik

  DOI：10.1016/j.tetlet.2018.03.014

  日期：2018.4

  Efficient syntheses of novel 10-aryl-5a-(arylamino)-9-hydroxy-5a,6,7,8-tetrahydroindeno[1,2-b]chromen-11(10H)-one derivatives has been reported by [4+2] cycloaddition reactions of electron-deficient 2-(arylmethylene)-1H-indene-1,3(2H)-dione heterodienes with electron-rich enaminones in [bmim]BF4 at 80 °C and in acetic acid at 80 °C. Dimedone/cyclohexane-1,3-dione enaminones have been used as dienophiles

  新颖10芳基-5-的高效合成一- （芳基氨基）-9-羟基-5-一个，6,7,8-四氢茚并[1,2- b ]苯并吡喃11（10 ħ） -酮衍生物已经报道由[ bmim] BF 4中在80°C和乙酸中，缺电子的2-（芳基亚甲基）-1 H-茚-1,3（2 H）-二酮杂二烯与富电子的烯酮的[4 + 2]环加成反应80°C时呈酸性。在反电子需量异Diels-Alder反应中，二甲酮/环己烷-1,3-二酮烯酮已被用作亲二烯体。通过简单的后处理即可以高收率获得产品。
• Regioselective and diastereoselective synthesis of two functionalized 1,5-methanoindeno[1,2-<i>d</i>]azocines <i>via</i> a three-component reaction
  作者：Jun Cao、Jing Sun、Chao-Guo Yan

  DOI：10.1039/c8ob00144h

  日期：——

  The morpholine promoted three-component reaction of N-alkylpiperidinone, indane-1,3-dione and 2-arylideneindane-1,3-dione in ethanol at room temperature resulted in the (1H-1,5-methanoindeno[1,2-d]azocin-12-ylidene)-1H-indene-1,3(2H)-dione derivatives in good yields and with exo-configuration. Under similar conditions, the reaction of N-alkylpiperidinone with 2-arylideneindane-1,3-dione afforded 7H-1

  在室温下，吗啉在乙醇中促进了N-烷基哌啶酮，茚满-1,3-二酮和2-芳撑茚满-1,3-二酮的三组分反应，生成了（1 H -1,5-甲亚胺[1,2] - d ]吖辛因-12-亚基）-1- ħ -茚-1,3（2 ħ）以良好的收率和与-二酮衍生物外-构型。在相似的条件下，N-烷基哌啶酮与2-芳基茚满-1,3-二酮的反应提供了7 H -1,5-甲亚甲基[1,2 - d ]偶氮电影-7,12-二酮，内含-配置。据信多米诺反应是用多米诺Knoevenagel缩合，迈克尔加成和醛醇缩合反应进行的。