(4R,5S)-4,5-Dimethyl-pyrrolidin-2-one | 138816-34-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (4R,5S)-4,5-Dimethyl-pyrrolidin-2-one
• 英文别名: (4R,5S)-4,5-dimethylpyrrolidin-2-one
• CAS: 138816-34-9
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: URLVRPKEOGBFHJ-UHNVWZDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one 在 copper(l) iodide 、 sodium naphthalenide 作用下， 以 乙二醇二甲醚 、 乙醚 为溶剂， 反应 7.67h， 生成 (4R,5S)-4,5-Dimethyl-pyrrolidin-2-one
  参考文献：
  名称：

  Transition metal catalyzed radical cyclization: new preparative route to .gamma.-lactams from allylic alcohols via the [3.3]-sigmatropic rearrangement of allylic trichloroacetimidates and the subsequent ruthenium-catalyzed cyclization of N-allyltrichloroacetamides

  摘要：

  A sequence of reactions including [3.3]-sigmatropic rearrangement of allyl trichloroacetimidates (Overman rearrangement) followed by ruthenium-catalyzed cyclization of N-allyltrichloroacetamides provided a novel method for preparing trichlorinated gamma-lactams from allylic alcohols. No delta-lactam was formed as a byproduct. The cyclization of secondary N-allyltrichloroacetamides proceeded with good diastereoselectivity. Two types of tandem cyclizations to form bicyclic lactams took place in the cyclization of N-allyltrichloroacetamides from geraniol and linalool.

  DOI：

  10.1021/jo00032a016

文献信息

• Preparation of γ- and δ-lactams by ring closure of β,γ-unsaturated amides using trifluoromethanesulfonic acid
  作者：Charles M. Marson、Asad Fallah

  DOI：10.1016/s0040-4039(00)76535-x

  日期：1994.1

  γ-Lactams and δ-lactams can be prepared by the reaction of β,γ-unsaturated amides with trifluoromethanesulfonic acid.

  γ-内酰胺和δ-内酰胺可以通过β，γ-不饱和酰胺与三氟甲磺酸反应来制备。
• PYRROLIDIN-2-ONE DERIVATIVES AS ANDROGEN RECEPTOR MODULATOR
  申请人：Hasuoka Atsushi

  公开号：US20110098336A1

  公开（公告）日：2011-04-28

  A compound represented by the formula (I) according to claim 1 or a salt thereof has a superior androgen receptor modulating action.

  根据权利要求1所述的公式（I）代表的化合物或其盐具有优异的雄激素受体调节作用。
• Transition metal-catalyzed radical cyclizations: a low-temperature process for the cyclization of N-protected N-allyltrichloroacetamides to trichlorinated .gamma.-lactams and application to the stereoselective preparation of .beta.,.gamma.-disubstituted .gamma.-lactams
  作者：Hideo Nagashima、Nobuyasu Ozaki、Masayuki Ishii、Koji Seki、Masayoshi Washiyama、Kenji Itoh

  DOI：10.1021/jo00054a034

  日期：1993.1

  Cyclizations of N-substituted N-allyltrichloroacetamides, where the substituent is an alkyl, Cbz, Boc, Ts, or Ms group, are catalyzed by a 1:1 mixture of CuCl and bipyridine to give the corresponding beta,gamma-trichlorinated gamma-lactams in high yields. The reactions proceed at temperatures from -78-degrees-C to room temperature. Cyclizations of N-allyltrichloroacetamides of acyclic secondary allylic amines are achieved with good selectivity; the cis/trans ratios of the gamma-lactams formed were dependent on the substituents on the nitrogen atom. The stereochemical outcome is compared with that of free-radical cyclization.
• Nouveaux composés aminopyrroline, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent
  申请人：LES LABORATOIRES SERVIER

  公开号：EP1101756B1

  公开（公告）日：2003-03-19
• US6300366B1
  申请人：——

  公开号：US6300366B1

  公开（公告）日：2001-10-09