(4S,5R)-4-butyl-5-methyl-1-(4-methylphenyl)sulfonylpyrrolidin-2-one | 138816-32-7

• 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: (4S,5R)-4-butyl-5-methyl-1-(4-methylphenyl)sulfonylpyrrolidin-2-one
• CAS: 138816-32-7
• 化学式: C₁₆H₂₃NO₃S
• 分子量: 309.43
• InChiKey: ZPMUJEMCJXOLML-KGLIPLIRSA-N

物化性质

• 沸点：
  428.8±38.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  21.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  54.45
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  1-tosyl-3-(phenylselenyl)-5-methyl-2-pyrrolidinone 在 sodium periodate 、 copper(l) iodide 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 3.17h， 生成 (4S,5R)-4-butyl-5-methyl-1-(4-methylphenyl)sulfonylpyrrolidin-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

• Conjugate addition of organocopper reagents to n-tosylated α, β-unsaturated amides
  作者：Hideo Nagashima、Nobuyasu Ozaki、Masayoshi Washiyama、Kenji ltoh

  DOI：10.1016/s0040-4039(00)89172-8

  日期：1985.1

  N-Tosylated α, β-unsaturated amides and lactams undergo facile conjugate addition with R2CuLi or RMgX/CuI (cat.). Stereoselective synthesis of trans-β,γ-dialkyl-γ-lactams can be achieved by this procedure. The resulting N-tosylamide moiety is further transformed to alcohol and several carbonyl compounds by way of reduction or nucleophillic displacement.

  N-甲苯磺酸化的α，β-不饱和酰胺和内酰胺与R 2 CuLi或RMgX / CuI（目录）轻松偶联。通过该方法可以实现反式-β，γ-二烷基-γ-内酰胺的立体选择性合成。通过还原或亲核取代，将所得的N-甲苯磺酰胺部分进一步转化为醇和几种羰基化合物。
• NAGASHIMA, HIDEO;OZAKI, NOBUYASU;WASHIYAMA, MASAYOSHI;ITOH, KENJI, TETRAHEDRON LETT., 1985, 26, N 5, 657-660
  作者：NAGASHIMA, HIDEO、OZAKI, NOBUYASU、WASHIYAMA, MASAYOSHI、ITOH, KENJI

  DOI：——

  日期：——