1-methyl-3,3-diphenyl-pyrrolidin-2-one | 20538-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-methyl-3,3-diphenyl-pyrrolidin-2-one
• 英文别名: 1-Methyl-3,3-diphenyl-pyrrolidin-2-on；2-Pyrrolidinone, 1-methyl-3,3-diphenyl-；1-methyl-3,3-diphenylpyrrolidin-2-one
• CAS: 20538-39-0
• 化学式: C₁₇H₁₇NO
• 分子量: 251.328
• InChiKey: JIGLHNCQVJAREG-UHFFFAOYSA-N

物化性质

• 熔点：
  146.5-147 °C
• 沸点：
  412.3±45.0 °C(Predicted)
• 密度：
  1.126±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methyl-3,3-diphenyl-pyrrolidin-2-one 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 1-methyl-3,3-diphenylpyrrolidine
  参考文献：
  名称：

  Morrison et al., Journal of the Chemical Society, 1951, p. 952,955

  摘要：

  DOI：
• 作为产物：
  描述：

  4-(dimethylamino)-2,2-diphenylbutanenitrile 在 盐酸 、 氯化亚砜 作用下， 生成 1-methyl-3,3-diphenyl-pyrrolidin-2-one
  参考文献：
  名称：

  Dupre et al., Journal of the Chemical Society, 1949, p. 500,505

  摘要：

  DOI：

文献信息

• Moffett; Aspergren, Journal of the American Chemical Society, 1957, vol. 79, p. 4462,4464, 4465
  作者：Moffett、Aspergren

  DOI：——

  日期：——
• Ocular toxicity study of trypan blue injected into the vitreous cavity of rabbit eyes
  作者：Marc Veckeneer、Koen Overdam、Jan Monzer、Karin Kobuch、Wilfried Marle、Henk Spekreijse、Jan Meurs

  DOI：10.1007/s004170100341

  日期：2001.9

  Background: To evaluate the ocular toxicity of trypan blue (TB) injected into the vitreous cavity of rabbit eyes. TB is a dye that could be useful for staining epiretinal membranes during vitrectomy surgery. Methods: Ten New Zealand White (NZW) rabbits underwent gas-compression vitrectomy. Rabbits were divided into three groups to receive injections of 0.1 ml basic salt solution, 0.1 ml of a 0.06% TB solution or 0.1 ml of a 0.2% TB solution. Ocular toxicity was assessed by slit-lamp biomicroscopy, ophthalmoscopy, electroretinography and histology. Results: Transient posterior capsule opacification was noted in all animals. No significant reductions in a-wave or b-wave amplitudes were found in any of the animals. Light and electron microscopic examination of the inferior retina in the 0.2% TB-treated eyes showed damaged photoreceptors and marked disorganization. Immunohistochemical staining for rhodopsin was strongly reduced in those sections and staining for proliferation with Ki-67 was positive. No histological abnormalities were found in the upper retina of the 0.2% TB-treated eyes or in any part of the retina of the 0.06% TB-treated or control eyes. No histological abnormalities were found in any of the anterior chamber angle specimens. Conclusions: Although no signs of toxicity were found after the prolonged presence of TB at a concentration of 0.06% in the vitreous cavity of rabbit eyes, marked damage occurred in the lower retina of 0.2% TB-treated eyes. The shortterm presence of TB at a concentration of 0.06% in the vitreous cavity is harmless to the rabbit eye but a higher concentration of TB could be unsafe.
• Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles
  作者：Kevin H. Shaughnessy、Blake C. Hamann、John F. Hartwig

  DOI：10.1021/jo980611y

  日期：1998.9.1

  2A palladium-catalyzed alpha-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)(2) (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave alpha-arylamides in 48 - 75% yield and N-methyl-alpha-phenyl pyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52-82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.
• King et al., Journal of the Chemical Society, 1952, p. 4268,4270
  作者：King et al.

  DOI：——

  日期：——
• Reactivity of N,N-dialkylamide enolate ions. Arylation of 1-methyl-2-pyrrolidinone enolate ions by the SRN1 mechanism
  作者：Ruben A. Alonso、Carlos H. Rodriguez、Roberto A. Rossi

  DOI：10.1021/jo00286a035

  日期：1989.12