(4S,5S)-4,5-Dimethyl-pyrrolidin-2-one | 138816-49-6

• 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: (4S,5S)-4,5-Dimethyl-pyrrolidin-2-one
• 英文别名: (4S,5S)-4,5-dimethylpyrrolidin-2-one
• CAS: 138816-49-6
• 化学式: C₆H₁₁NO
• 分子量: 113.159
• InChiKey: URLVRPKEOGBFHJ-WHFBIAKZSA-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：

  N-<(3-butenyl)> trichloroacetamide 在 tris(triphenylphosphine)ruthenium(II) chloride 偶氮二异丁腈 、 三正丁基氢锡 作用下， 生成 (4R,5S)-4,5-Dimethyl-pyrrolidin-2-one 、 (4S,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

• Bicyclic And Tricyclic Derivatives As Thrombin Receptor Antagonists
  申请人：Chackalamannil Samuel

  公开号：US20080090830A1

  公开（公告）日：2008-04-17

  Heterocyclic-substituted tricyclics of the formula or a pharmaceutically acceptable salt or solvate of said compound, isomer or racemic mixture wherein represents an optional double bonds the dotted line is optionally a bond or no bonds resulting in a double bond or a single bond, as permitted by the valency requirement and wherein E, A, G M, Het, B, X, R 3 , R 10 , R 11 , R 32 and R 33 are herein defined and the remaining substituents are as defined in the specification, are disclosed, as well as pharmaceutical compositions containing them and a method of treating diseases associated with thrombosis, atherosclerosis, restenosis, hypertension, angina pectoris, arrhythmia, heart failures and cancer by administering said compounds. Combination therapy with other cardiovascular agents is also claimed.

  具有以下结构的杂环取代的三环化合物，或者该化合物的药用盐或溶剂化合物、异构体或消旋混合物，其中表示一个可选的双键，虚线可以是一个键或无键，从而形成一个双键或一个单键，符合化合价要求，E、A、G、M、Het、B、X、R3、R10、R11、R32和R33在此有定义，其余取代基如规范中所定义，以及含有它们的药物组合物和通过给予该化合物治疗与血栓形成、动脉粥样硬化、再狭窄、高血压、心绞痛、心律失常、心力衰竭和癌症相关的疾病的方法。还声称与其他心血管药物的联合疗法。
• 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。
• 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
• US8153664B2
  申请人：——

  公开号：US8153664B2

  公开（公告）日：2012-04-10