N-acetyl-2-chloro-N-methylacetamide | 51892-54-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-acetyl-2-chloro-N-methylacetamide
• CAS: 51892-54-7
• 化学式: C₅H₈ClNO₂
• mdl: MFCD19236591
• 分子量: 149.577
• InChiKey: MTMQULAXWHFSNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-acetyl-2-chloro-N-methylacetamide 在 sodium azide 、 三苯基膦 作用下， 以 二甲基亚砜 、 甲苯 为溶剂， 反应 24.0h， 生成 1,2-二甲基-1H-咪唑-5-(4H)-酮
  参考文献：
  名称：

  Tuning the solid-state emission of the analogous GFP chromophore by varying alkyl chains in the imidazolinone ring

  摘要：

  具有不同长度烷基链的绿色荧光蛋白（GFP）类色素分子GFP-C_n（n = 1, 3, 5, 11）在咪唑啉酮环中被合成，并确定了它们的晶体结构。这些GFP类色素分子在固态下均能发光，并且随着烷基链长度的增加，固态发光量子产率提高，这是由于基于它们晶体结构的分子间π-π相互作用显著减弱所致。

  DOI：

  10.1007/s11426-013-4913-x
• 作为产物：
  描述：

  N-甲基乙酰胺 、 氯乙酰氯 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 N-acetyl-2-chloro-N-methylacetamide
  参考文献：
  名称：

  Tuning the solid-state emission of the analogous GFP chromophore by varying alkyl chains in the imidazolinone ring

  摘要：

  具有不同长度烷基链的绿色荧光蛋白（GFP）类色素分子GFP-C_n（n = 1, 3, 5, 11）在咪唑啉酮环中被合成，并确定了它们的晶体结构。这些GFP类色素分子在固态下均能发光，并且随着烷基链长度的增加，固态发光量子产率提高，这是由于基于它们晶体结构的分子间π-π相互作用显著减弱所致。

  DOI：

  10.1007/s11426-013-4913-x

文献信息

• Tuning the solid-state emission of the analogous GFP chromophore by varying alkyl chains in the imidazolinone ring
  作者：Xiang Shen、GuangXi Huang、Kan Li、GuanXin Zhang、DeQing Zhang

  DOI：10.1007/s11426-013-4913-x

  日期：2013.9

  New analogues of green fluorescent protein (GFP) chromophore m GFP-C n (n = 1, 3, 5, 11) with alkyl chains of different lengths in the imidazolinone rings were synthesized and their crystal structures were determined. These GFP-like chromophores are all emissive in the solid state. And the solid-state emission quantum yields of increase by extending the lengths of alkyl chains, owing to the fact that the intermolecular pi-pi interactions are significantly weakened based on their crystal structures.

  具有不同长度烷基链的绿色荧光蛋白（GFP）类色素分子GFP-C_n（n = 1, 3, 5, 11）在咪唑啉酮环中被合成，并确定了它们的晶体结构。这些GFP类色素分子在固态下均能发光，并且随着烷基链长度的增加，固态发光量子产率提高，这是由于基于它们晶体结构的分子间π-π相互作用显著减弱所致。
• Syntheses of Highly Fluorescent GFP-Chromophore Analogues
  作者：Liangxing Wu、Kevin Burgess

  DOI：10.1021/ja710388h

  日期：2008.3.1

  Eight B-containing compounds, i.e., 1a-h, were prepared as mimics of the green fluorescent protein (GFP) fluorophore. The underlying concept was that synthetic GFP chromophore analogues are not fluorescent primarily because of free rotation about an aryl-alkene bond (Figure 1b). This rotation is not possible in the beta-barrel of GFP; hence, the molecule is strongly fluorescent. In compounds 1a-h, radiationless decay via this mechanism is prevented by complexation of the BF2 entity. The target materials were prepared via two methods; most were obtained according to the novel route shown in Scheme 1 b, but compound 1f was made via the procedure described in Scheme 2. Both syntheses involved formation of undesired compounds E-4a-h that formed simultaneously with the desired isomeric intermediates Z-4a-h. Both compounds form BF2 adducts, i.e., 1 a-h and 5a-h, respectively. Methods used for spectroscopic characterization and differentiation of compounds in the series 1 and 5 are discussed, and these are supported by single-crystal X-ray diffraction analyses for compounds 1c, 5c, 1f, and 5f. Electronic spectra of compounds la-h and 5a-h were studied in detail. Those in the 5 series were shown to be only weakly fluorescent, but the 1 series were strongly fluorescent compounds (comparable to the boraindacene, BODIPY, dyes). Compounds 1g and 1h are water soluble, and 1h has particularly significant potential as a probe, since it also has a carboxylic acid group for attachment to biomolecules.
• Locked <i>ortho</i>- and <i>para</i>-Core Chromophores of Green Fluorescent Protein; Dramatic Emission Enhancement via Structural Constraint
  作者：Yen-Hao Hsu、Yi-An Chen、Huan-Wei Tseng、Zhiyun Zhang、Jiun-Yi Shen、Wei-Ti Chuang、Tzu-Chieh Lin、Chun-Shu Lee、Wen-Yi Hung、Bor-Cherng Hong、Shih-Hung Liu、Pi-Tai Chou

  DOI：10.1021/ja5062856

  日期：2014.8.20

  We report the design strategy and synthesis of a structurally locked GFP core chromophore p-LHBDI, its ortho-derivative, o-LHBDI, and H2BDI possessing both para- and ortho-hydroxyl groups such that the inherent rotational motion of the titled compounds has been partially restricted. o-LHBDI possesses a doubly locked configuration, i.e., the seven-membered ring hydrogen bond and five-membered ring C(4-5-10-13-14) cyclization, from which the excited-state intramolecular proton transfer takes place, rendering a record high tautomer emission yield (0.18 in toluene) and the generation of amplified spontaneous emission. Compared with their unlocked counterparts, a substantial increase in the emission yield is also observed for p-LHBDI and H2BDI in anionic forms in water, and accordingly the structure versus luminescence relationship is fully discussed based on their chemistry and spectroscopy aspect. In solid, o-LHBDI exhibits an H-aggregate-like molecular packing, offers narrow-bandwidth emission, and has been successfully applied to fabricate a yellow organic light emitting diodes (λmax = 568 nm, ηext = 1.9%) with an emission full width at half-maximum as narrow as 70 nm.