1,2-dibenzoyl-1,1,2,2-tetradeuteroethane | 97405-82-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-dibenzoyl-1,1,2,2-tetradeuteroethane
• 英文别名: 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione；1,2-Dibenzoyl-1,1,2,2-tetradeuterioethane；1,2-Dibenzoyltetradeuteroethan；1,1,2,2-Tetradeuterio-1,2-dibenzoylethan；2,2,3,3-tetradeuterio-1,4-diphenyl-butane-1,4-dione；2,2,3,3-Tetradeuterio-1,4-diphenylbutane-1,4-dione
• CAS: 97405-82-8
• 化学式: C₁₆H₁₄O₂
• 分子量: 242.254
• InChiKey: OSWWFLDIIGGSJV-AREBVXNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,2-dibenzoyl-1,1,2,2-tetradeuteroethane 在 三氢化钐 作用下， 以 四氢呋喃 为溶剂， 以68%的产率得到2,2-Dideuterio-1-phenylcyclopropane
  参考文献：
  名称：

  Imamoto, Tsuneo; Hatajima, Toshihiko; Takiyama, Nobuyuki, Journal of the Chemical Society. Perkin transactions I, 1991, # 12, p. 3127 - 3135

  摘要：

  DOI：
• 作为产物：
  描述：

  二苯甲酰基乙炔 在 氘代甲醇 、 Woollins 试剂 作用下， 生成 1,2-dibenzoyl-1,1,2,2-tetradeuteroethane
  参考文献：
  名称：

  Woollins Reagent: A Chemoselective Reducing Agent for 1,4-Enediones and 1,4-Ynediones to Saturated 1,4-Diones

  摘要：

  Woollins reagent was found to act as a highly chemoselective reagent for the reduction of a wide range of 1,4-enediones and 1,4-ynediones in methanol to afford the corresponding saturated 1,4-diketones in good yields under mild reaction conditions.

  DOI：

  10.1055/s-0032-1317343

文献信息

• The reaction of carbonyl compounds with diiodomethane in the presence of samarium: Novel syntheses of iodohydrins and cyclopropanols
  作者：Tsuneo Imamoto、Toshiaki Takeyama、Hiroyasu Koto

  DOI：10.1016/s0040-4039(00)84764-4

  日期：1986.1

  The iodomethylation of carbonyl compounds giving iodohydrins has been achieved under ordinary conditions by the use of diiodomethane and samarium. A novel synthesis of cyclopropanols from α-haloketones or 1,2-dibenzoylethane is also described.

  在通常条件下，通过使用二碘甲烷和sa可以实现羰基化合物的碘甲基化，从而得到碘醇。还描述了由α-卤代酮或1，2-二苯甲酰基乙烷新型合成环丙醇。
• Intermediates in the Paal-Knorr synthesis of pyrroles
  作者：Venkataraman Amarnath、Douglas C. Anthony、Kalyani Amarnath、William M. Valentine、Lawrence A. Wetterau、Doyle G. Graham

  DOI：10.1021/jo00024a040

  日期：1991.11

  The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored. In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m). This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step. The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:03:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.
• IMAMOTO TSUNEO; TAKEYAMA TOSHIAKI; KOTO HIROYASU, TETRAHEDRON LETT., 27,(1986) N 28, 3243-3246
  作者：IMAMOTO TSUNEO、 TAKEYAMA TOSHIAKI、 KOTO HIROYASU

  DOI：——

  日期：——