(S)-2,2,5,5-tetrahydro-1,5-dimethyl-4-phenyl-2(1H)-pyrrolone | 161297-29-6

• 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: (S)-2,2,5,5-tetrahydro-1,5-dimethyl-4-phenyl-2(1H)-pyrrolone
• 英文别名: (S)-(+)-1,5-Dimethyl-4-phenyl-1,5-dihydro-2H-pyrrol-2-on；(5S)-1,5-dimethyl-4-phenyl-1,5-dihydropyrrol-2-one；(2S)-1,2-dimethyl-3-phenyl-2H-pyrrol-5-one
• CAS: 161297-29-6
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: QLCPYHKRCGVOOA-VIFPVBQESA-N

物化性质

• 熔点：
  129-131 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  352.5±32.0 °C(Predicted)
• 密度：
  1.090±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (S)-2,2,5,5-tetrahydro-1,5-dimethyl-4-phenyl-2(1H)-pyrrolone 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 (4S,5S)-1,5-Dimethyl-4-phenyl-pyrrolidin-2-one 、 (4R,5S)-(-)-1,5-Dimethyl-4-phenyl-2-pyrrolidinon
  参考文献：
  名称：

  Chelucci, Giorgio; Saba, Antonio, Angewandte Chemie, 1995, vol. 107, # 1, p. 104 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  (-)-N-benzoyl-ephedrine 在 盐酸 、 正丁基锂 、 乙醇 、 Celite 、 甲基锂 、 叔丁基锂 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 14.0h， 生成 (S)-2,2,5,5-tetrahydro-1,5-dimethyl-4-phenyl-2(1H)-pyrrolone
  参考文献：
  名称：

  Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis

  摘要：

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.

  DOI：

  10.1016/0957-4166(95)00271-p

文献信息

• Reactivity of cyclic sulfamidates towards sulfur-stabilised enolates. Stereocontrolled synthesis of functionalised lactams
  作者：John F. Bower、Suda Chakthong、Jakub Švenda、Andrew J. Williams、Ron M. Lawrence、Peter Szeto、Timothy Gallagher

  DOI：10.1039/b601804a

  日期：——

  A structurally representative series of 1,2- and 1,3-cyclic sulfamidates react with enolates derived from methyl α-phenylthioacetate 9b to give 5- and 6-substituted α-phenylthio lactams 20–24. These products provide, via the corresponding sulfoxides, an entry to α,β-unsaturated lactams e.g.12, 27, 29 and their α-phenylthio analogues e.g.26 and 30. With the enantiomerically pure 1,2-cyclic sulfamidates 10, 15 and 17, these reactions all proceed with no detectable loss of stereochemical integrity.

  一系列结构上具有代表性的1,2-和1,3-环状硫酰胺与来源于甲基α-苯硫乙酸酯9b的烯醇盐发生反应，生成5-和6-取代的α-苯硫内酰胺20–24。这些产物通过相应的亚砜，为α,β-不饱和内酰胺（例如12、27、29）及其α-苯硫类似物（例如26和30）提供了一个合成途径。使用对映体纯净的1,2-环状硫酰胺10、15和17，所有这些反应均在没有可检测的立体化学完整性损失的情况下进行。
• Stereospecific course of a transannular CH insertion process
  作者：Giorgio Chelucci、Antonio Saba、Giovanni Valle

  DOI：10.1016/0957-4166(95)00077-3

  日期：1995.3

  The steric course of the catalytic decomposition of the chiral diazoxazepanedione 1 to 2-pyrrolone 3 was clarified by the X-ray diffraction study of the enantiomerically pure pyrrolidine 5, obtained by reductive cleavage of the unisolated intermediate bicyclic compound 2.
• Diastereoselective preparation of chiral lithiated allyl amines: Application in EPC-synthesis
  作者：Miguel Yus、Francisco Foubelo、Larry R. Falvello

  DOI：10.1016/0957-4166(95)00271-p

  日期：1995.8

  Lithiation of chiral allylamine (R)-1 with Bu(n)Li and Bu(t)Li leads to the formation of intermediate (R)-2, which by reaction with D2O, Me(2)CO or (CH2)(5)CO affords the expected chiral compounds (R)-3, (R)-4 and (R)-5, respectively. With Bu(1)CHO the corresponding aminoalcohols (R,R)6 and(R,S)-6 are separated in pure form by their transformation into the corresponding benzamides 6', which yield again the precursor aminoalcohols with MeLi. The carbonation of (R)-2 followed by esterification affords the unexpected ester trans- (R)-7. The same set of reactions is carried out with (S)-1 yielding the corresponding series of(S) derivatives. X-Ray analysis of(S,S)-6' allows the assignement of the stereochemistry for all aminoalcohols 6. The same processes are applied to more substituted chiralamines (R)- and (S)-11 obtaining the corresponding chiral products (R)- and (S)-13 and (S)-14.
• Chelucci, Giorgio; Saba, Antonio, Angewandte Chemie, 1995, vol. 107, # 1, p. 104 - 106
  作者：Chelucci, Giorgio、Saba, Antonio

  DOI：——

  日期：——