3,3-Di(n-butyl)phthalid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 3,3-Di(n-butyl)phthalid
• 英文别名: Dibutylphthalide；3,3-dibutyl-2-benzofuran-1-one
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: OGSQZNVXHNZJSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯酞 、 正丁基锂 以 四氢呋喃 、 正己烷 为溶剂， 以34%的产率得到3,3-Di(n-butyl)phthalid
  参考文献：
  名称：

  Umsetzungen der lithiierten Halbsandwich-Komplexe (CO)3MC5H4Li (M = Mn, Re) mit organischen carbonylverbindungen

  摘要：

  The reactions of the lithiated half-sandwich complex (CO)(3)MnC5H4-Li([Cym]-Li, 2a) with derivatives of organic dicarboxylic acids have been investigated with the goal of introducing several cymantrenyl ([Cym]) substituents in close proximity into organic molecules. The carboxylic acid chlorides of terephthalic and fumaric acid give, after reaction with excess 2a in THF solution and chromatography of the primary lithium compounds on silica, the bis(dicymantrenylcarbinols), [Cym]C-2(OH)-C6H4-C(OH)[Cym](2) (13a) and E-[Cym]C-2(OH)-CH=CH-C(OH)[Cym](2) (17a) which contain four cymantrenyl units. Phthaloyl chloride produces a product with isobenzofuranol skeleton and three cymantrenyl substituents. Cyclic anhydrides such as maleic and phthalic anhydride lead to lactons containing two geminal cymantrenyl groups.With chloroformates, the lithiated derivatives of cymantrene and cyrhetrene, (CO)(3)MC(5)H(4)-Li (M = Mn (2a), Re (2b)) can be directly converted to tris(cymantrenyl)- and tris(cyrhetrenyl) carbinol, [Cym]C-3-OH (18a) and [Cyr]C-3-OH (18b), respectively. In the presence of paraformaldehyde complexes 2a,b are first converted into the hydroxymethyl compounds (CO)(3)MC(5)H(4)-CH2OH (M = Mn (21a), Re (21b)) which then react, by further lithiation and formaldehyde insertion steps, to give 1,2-bis(hydroxymethyl) half-sandwiches, (CO)(3)MC(5)H(3)(CH2OH)(2)(M = Mn (22a), Re (22b)). Starting from thionyl chloride and 2a, dicymantrenyl sulfoxide, [Cym]2SO (28a), is obtained. The new complexes have been characterized on the basis of their H-1 and C-13 NMR data.

  DOI：

  10.1016/0022-328x(95)05552-z

文献信息

• ORGANIC COMPOUND, THREE-DIMENSIONAL ORGANIC FRAMEWORK FORMED BY USING ORGANIC COMPOUND, SEPARATION SIEVE AND OPTICAL LAYER, WHICH COMPRISE ORGANIC FRAMEWORK, AND OPTICAL DEVICE COMPRISING OPTICAL LAYER AS OPTICAL AMPLIFICATION LAYER
  申请人：INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY

  公开号：US20190031586A1

  公开（公告）日：2019-01-31

  An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.

  提供一种有机化合物，通过使用该有机化合物形成的三维有机结构、分离筛和具有该有机结构的光学层，以及具有光学层作为光学放大层的光学器件。该有机结构包括通过非共价键自组装的多个有机分子。每个单元有机分子具有芳香环，第一对取代基连接到芳香环的可取代位置的相邻位置，第二对取代基连接到芳香环的剩余可取代位置的相邻位置。单元有机分子通过范德华力相互作用、伦敦分散相互作用或氢键作用于第一和第二对取代基之间的π-π相互作用而自组装。
• Organic compound, three-dimensional organic framework formed by using organic compound, separation sieve and optical layer, which comprise organic framework, and optical device comprising optical layer as optical amplification layer
  申请人：INDUSTRY-UNIVERSITY COOPERATION FOUNDATION HANYANG UNIVERSITY

  公开号：US11066351B2

  公开（公告）日：2021-07-20

  An organic compound, a three-dimensional organic structure formed by using the organic compound, a separation sieve and an optical layer having the organic structure, and an optical device having the optical layer as an optical amplification layer are provided. The organic structure includes a plurality of organic molecules self-assembled by non-covalent bonding. Each of the unit organic molecules has an aromatic ring, a first pair of substituents being connected to immediately adjacent positions of substitutable positions of the aromatic ring, and a second pair of substituents being connected to immediately adjacent positions of remaining substitutable positions of the aromatic ring. The unit organic molecules are self-assembled by van der Waals interaction, London dispersion interaction or hydrogen bonding between the first and the second pairs of the substituents and by pi-pi interactions between the aromatic rings.

  本文提供了一种有机化合物、利用该有机化合物形成的三维有机结构、具有该有机结构的分离筛和光学层，以及具有该光学层作为光放大层的光学设备。有机结构包括多个通过非共价键自组装的有机分子。每个单元有机分子都有一个芳香环，第一对取代基连接到芳香环可取代位置的紧邻位置，第二对取代基连接到芳香环其余可取代位置的紧邻位置。通过第一对和第二对取代基之间的范德华相互作用、伦敦色散相互作用或氢键作用，以及芳香环之间的π-π相互作用，单元有机分子得以自组装。
• Umsetzungen der lithiierten Halbsandwich-Komplexe (CO)3MC5H4Li (M = Mn, Re) mit organischen carbonylverbindungen
  作者：Max Herberhold、Martin Biersack

  DOI：10.1016/0022-328x(95)05552-z

  日期：1995.11

  The reactions of the lithiated half-sandwich complex (CO)(3)MnC5H4-Li([Cym]-Li, 2a) with derivatives of organic dicarboxylic acids have been investigated with the goal of introducing several cymantrenyl ([Cym]) substituents in close proximity into organic molecules. The carboxylic acid chlorides of terephthalic and fumaric acid give, after reaction with excess 2a in THF solution and chromatography of the primary lithium compounds on silica, the bis(dicymantrenylcarbinols), [Cym]C-2(OH)-C6H4-C(OH)[Cym](2) (13a) and E-[Cym]C-2(OH)-CH=CH-C(OH)[Cym](2) (17a) which contain four cymantrenyl units. Phthaloyl chloride produces a product with isobenzofuranol skeleton and three cymantrenyl substituents. Cyclic anhydrides such as maleic and phthalic anhydride lead to lactons containing two geminal cymantrenyl groups.With chloroformates, the lithiated derivatives of cymantrene and cyrhetrene, (CO)(3)MC(5)H(4)-Li (M = Mn (2a), Re (2b)) can be directly converted to tris(cymantrenyl)- and tris(cyrhetrenyl) carbinol, [Cym]C-3-OH (18a) and [Cyr]C-3-OH (18b), respectively. In the presence of paraformaldehyde complexes 2a,b are first converted into the hydroxymethyl compounds (CO)(3)MC(5)H(4)-CH2OH (M = Mn (21a), Re (21b)) which then react, by further lithiation and formaldehyde insertion steps, to give 1,2-bis(hydroxymethyl) half-sandwiches, (CO)(3)MC(5)H(3)(CH2OH)(2)(M = Mn (22a), Re (22b)). Starting from thionyl chloride and 2a, dicymantrenyl sulfoxide, [Cym]2SO (28a), is obtained. The new complexes have been characterized on the basis of their H-1 and C-13 NMR data.