2-benzoyl-1,3-indandione | 27963-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-benzoyl-1,3-indandione
• 英文别名: 3-hydroxy-2-(phenylcarbonyl)-1H-inden-1-one；2-[hydroxy(phenyl)methylidene]indene-1,3-dione
• CAS: 27963-46-8
• 化学式: C₁₆H₁₀O₃
• 分子量: 250.254
• InChiKey: LMYFYBHZOMGFRR-UHFFFAOYSA-N

物化性质

• 沸点：
  447.0±45.0 °C(Predicted)
• 密度：
  1.388±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 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：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-benzoyl-1,3-indandione 在 氯化亚砜 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 生成 (±)-3',3'-dimethyl-7a'-phenyl-2'H-spiro[indene-2,7'-pyrrolo[2,1-b]oxazole]-1,3,5'(3'H,6'H,7a'H)-trione
  参考文献：
  名称：

  简单访问功能强大的双环γ-和δ-内酰胺：DFT评估手性转移至连续的第三/四级立体中心的起源

  摘要：

  本文描述了通过多米诺法合成多取代的恶唑并吡咯烷酮和哌啶子酮的方法。该方法基于羟基卤代酰胺与迈克尔受体之间的反应，该反应可有效生成双环内酰胺。该过程与迈克尔受体上的不对称吸电子基团兼容，从而可以形成两个连续且完全受控的三级和四级立体中心。在四取代的迈克尔受体的情况下，两个相邻的季立体中心以良好的产率形成。从（R）-苯基甘氨醇衍生的酰胺导致收率高到低且立体选择性高的对映体富集的双环内酰胺的形成，因此大大增加了该策略的范围和兴趣。通过DFT计算研究了手性转移和非对映选择性的起源，并将其归因于反应顺序的最后两个步骤之一中的动力学控制。该选择性取决于迈克尔受体上的取代基和钠阳离子螯合。

  DOI：

  10.1002/chem.201405094
• 作为产物：
  描述：

  邻苯二甲酸二甲酯 、 苯乙酮 在 sodium methylate 作用下， 以 甲苯 为溶剂， 生成 2-benzoyl-1,3-indandione
  参考文献：
  名称：

  Luminescence properties of 2-benzoyl-1,3-indandione based Eu3+ ternary and tetrakis complexes and their polymer films

  摘要：

  Six new Europium (III) complexes with ternary and tetrakis structures - Eu(BID)(3)(PHEN), Eu(MBID)(3)(PHEN), [Eu (BID)(4)]N--(+)(Et)(4), [Eu(MBID)4]N--(+)(Et)(4), [Eu(BID)4]N--(+)(Bu)(4), and [Eu(MBID)(4)]N--(+)(Bu)(4) (BID - 2-benzoyl1,3-indandionate, MBID - 2-(4-methylbenzoyI)-1,3-indandionate and PHEN - 1,10-phenantroline) are synthesized, characterized, and incorporated into poly-N-vinylcarbazole (PVK) and poly methyl methacrylate (PMMA) matrices. Complex structure shows significant effect on thermal properties and emission properties of complexes in solid-state. Used countercations (N+(Et)(4) or N+(Bu)(4)) greatly affects complex solubility in solvents, absolute photoluminescence quantum yields and photoluminescence lifetimes in solid-state. Complexes exhibit red-light emission attributed to D-5(0)-> F-7(J) (J = 0-4) transitions of Eu3+ ion with moderate to high quantum yields (0.06-0.60), bi-exponential lifetimes and pure red-light CIE chromaticity coordinates (x = 0.670; y = 0.330) in solid-state. Incorporation of synthesized complexes in PVK matrices leads to significant emission intensity and quantum yield decrease.However, doped PMMA films with synthesized complexes exhibit moderate PLQY (0.09-0.14) and longer lifetime values than in solid-state and could show potential application as polymer optical fibers or in OLED's and other devices.

  DOI：

  10.1016/j.dyepig.2018.07.003

文献信息

• USOVA T. L.; KORCHEVIN N. A.; USOV V. A.; BOPOHKOB M. G., ZH. ORGAN. XIMII, 1980, 16, HO 8, 1789-1790
  作者：USOVA T. L.、 KORCHEVIN N. A.、 USOV V. A.、 BOPOHKOB M. G.

  DOI：——

  日期：——
• Luminescence properties of 2-benzoyl-1,3-indandione based Eu3+ ternary and tetrakis complexes and their polymer films
  作者：Ilze Malina、Valdis Kampars、Sergey Belyakov

  DOI：10.1016/j.dyepig.2018.07.003

  日期：2018.12

  Six new Europium (III) complexes with ternary and tetrakis structures - Eu(BID)(3)(PHEN), Eu(MBID)(3)(PHEN), [Eu (BID)(4)]N--(+)(Et)(4), [Eu(MBID)4]N--(+)(Et)(4), [Eu(BID)4]N--(+)(Bu)(4), and [Eu(MBID)(4)]N--(+)(Bu)(4) (BID - 2-benzoyl1,3-indandionate, MBID - 2-(4-methylbenzoyI)-1,3-indandionate and PHEN - 1,10-phenantroline) are synthesized, characterized, and incorporated into poly-N-vinylcarbazole (PVK) and poly methyl methacrylate (PMMA) matrices. Complex structure shows significant effect on thermal properties and emission properties of complexes in solid-state. Used countercations (N+(Et)(4) or N+(Bu)(4)) greatly affects complex solubility in solvents, absolute photoluminescence quantum yields and photoluminescence lifetimes in solid-state. Complexes exhibit red-light emission attributed to D-5(0)-> F-7(J) (J = 0-4) transitions of Eu3+ ion with moderate to high quantum yields (0.06-0.60), bi-exponential lifetimes and pure red-light CIE chromaticity coordinates (x = 0.670; y = 0.330) in solid-state. Incorporation of synthesized complexes in PVK matrices leads to significant emission intensity and quantum yield decrease.However, doped PMMA films with synthesized complexes exhibit moderate PLQY (0.09-0.14) and longer lifetime values than in solid-state and could show potential application as polymer optical fibers or in OLED's and other devices.
• Simple Access to Highly Functional Bicyclic γ- and δ-Lactams: Origins of Chirality Transfer to Contiguous Tertiary/Quaternary Stereocenters Assessed by DFT
  作者：Ronan Le Goff、Arnaud Martel、Morgane Sanselme、Ata Martin Lawson、Adam Daïch、Sébastien Comesse

  DOI：10.1002/chem.201405094

  日期：2015.2.9

  Michael acceptors, which leads efficiently to bicyclic lactams. The process is compatible with unsymmetrical electron‐withdrawing groups on the Michael acceptor, which allows the formation of two contiguous and fully controlled tertiary and quaternary stereocenters. In the case of tetrasubstituted Michael acceptors, two adjacent quaternary stereocenters are formed in good yield. Starting from (R)‐phenylglycinol

  本文描述了通过多米诺法合成多取代的恶唑并吡咯烷酮和哌啶子酮的方法。该方法基于羟基卤代酰胺与迈克尔受体之间的反应，该反应可有效生成双环内酰胺。该过程与迈克尔受体上的不对称吸电子基团兼容，从而可以形成两个连续且完全受控的三级和四级立体中心。在四取代的迈克尔受体的情况下，两个相邻的季立体中心以良好的产率形成。从（R）-苯基甘氨醇衍生的酰胺导致收率高到低且立体选择性高的对映体富集的双环内酰胺的形成，因此大大增加了该策略的范围和兴趣。通过DFT计算研究了手性转移和非对映选择性的起源，并将其归因于反应顺序的最后两个步骤之一中的动力学控制。该选择性取决于迈克尔受体上的取代基和钠阳离子螯合。