5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one | 96013-62-6

• 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: 5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one
• 英文别名: N-tosyl-5-methyl-3-pyrrolin-2-one；2-methyl-1-(4-methylphenyl)sulfonyl-2H-pyrrol-5-one
• CAS: 96013-62-6
• 化学式: C₁₂H₁₃NO₃S
• 分子量: 251.306
• InChiKey: PGQWTQRCHFCFNB-UHFFFAOYSA-N

物化性质

• 沸点：
  387.9±45.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one 在 copper(l) iodide 萘 、 sodium 作用下， 以 乙醚 为溶剂， 反应 5.5h， 生成 threo-(4S,5S)-5-methyl-4-phenylpyrrolidin-2-one
  参考文献：
  名称：

  将有机铜试剂加到正甲苯基化的α，β-不饱和酰胺上

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)89172-8
• 作为产物：
  描述：

  4-oxo-N-tosylpentanamide 在 对甲苯磺酸 作用下， 以 水 、 甲苯 为溶剂， 生成 5-methyl-1-tosyl-1,5-dihydro-2H-pyrrol-2-one
  参考文献：
  名称：

  铜催化 γ-取代 α,β-不饱和 γ-内酰胺的不对称动力学硼共轭加成

  摘要：

  据报道，Cu 催化的 γ-取代的 α,β-不饱和 γ-内酰胺的不对称动态硼共轭加成反应随后进行氧化，取得了良好的结果。该策略提供了一种有效获得有价值的对映体富集的α,β-不饱和γ-内酰胺的途径，该内酰胺带有简单的γ-烷基或芳基取代基，其对顺铂敏感的卵巢癌细胞A2780表现出抑制活性。提出了一种新的路易斯酸铜催化机理。

  DOI：

  10.1002/anie.202304640

文献信息

• Iridium-Catalyzed Intramolecular Oxidative Cyclization of Alkenyl Amides and Alkenoic Acids
  作者：Takahiro Nishimura、Midori Nagamoto、Hideki Yorimitsu

  DOI：10.1055/s-0036-1588435

  日期：2017.9

  Published as part of the Special Topic Modern Cyclization Strategies in Synthesis Abstract An iridium/dppf complex efficiently catalyzed the oxidative cyclization of N-sulfonyl alkenyl amides and alkenoic acids. Electron-deficien­t alkenes were effective as sacrificial hydrogen acceptors. High selectivity of the oxidative cyclization over the competing addition reaction has been realized by the use

  作为专题“现代合成中的环化策略”的一部分发布 抽象的 铱/ dppf络合物可有效催化N-磺酰基烯基酰胺和烯酸的氧化环化。缺电子的烯烃有效地用作牺牲氢受体。通过使用NaI作为添加剂已经实现了在竞争性加成反应中氧化环化的高选择性。 铱/ dppf络合物可有效催化N-磺酰基烯基酰胺和烯酸的氧化环化。缺电子的烯烃有效地用作牺牲氢受体。通过使用NaI作为添加剂已经实现了在竞争性加成反应中氧化环化的高选择性。
• Pd-catalyzed 5-endo-trig-type cyclization of β,γ-unsaturated carbonyl compounds: an efficient ring closing reaction to give γ-butenolides and 3-pyrrolin-2-ones
  作者：Gan B. Bajracharya、Priti S. Koranne、Rashid N. Nadaf、Randa Kassem Mohamed Gabr、Kazuhiro Takenaka、Shinobu Takizawa、Hiroaki Sasai

  DOI：10.1039/c0cc02352c

  日期：——

  The 5-endo-trig-type cyclization has been performed using a Pd-bis(isoxazoline) catalyst. The present cyclization of beta,gamma-unsaturated carbonyl compounds gave gamma-butenolides and 3-pyrrolin-2-ones in good to excellent yields.

  已经使用Pd-双（异恶唑啉）催化剂进行了5-内-trig-型环化。β，γ-不饱和羰基化合物的当前环化以良好至优异的产率得到γ-丁烯内酯和3-吡咯啉-2-酮。
• Enantioselective direct vinylogous Michael addition for constructing enantioenriched γ,γ-dialkyl substituted butyrolactams and octahydroindoles
  作者：Jiahang Yan、Wenting Zhang、Qiaoqiao He、Jun Hou、Hongxin Zeng、Hongbo Wei、Weiqing Xie

  DOI：10.1039/d2ob00112h

  日期：——

  A nickel(II)-catalyzed asymmetric direct vinylogous Michael addition of γ-alkyl monosubstituted α,β-unsaturated butyrolactams to α,β-unsaturated carbonyl compounds has been disclosed, affording γ,γ-dialkyl substituted butyrolactams in good yields and satisfactory enantioselectivities. A tandem catalytic asymmetric vinylogous Michael addition/intramolecular Michael addition has also been developed based

  镍( II )催化的γ-烷基单取代的α,β-不饱和丁内酰胺与α,β-不饱和羰基化合物的不对称直接乙烯基Michael加成，以良好的收率和令人满意的对映选择性得到γ,γ-二烷基取代的丁内酰胺。基于该反应还开发了串联催化不对称插烯迈克尔加成/分子内迈克尔加成，这使得能够构建具有三个连续立体碳中心的对映体富集的八氢吲哚。
• 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
  作者：Hideo Nagashima、Hidetoshi Wakamatsu、Nobuyasu Ozaki、Tsutomu Ishii、Masakazu Watanabe、Tomonori Tajima、Kenji Itoh

  DOI：10.1021/jo00032a016

  日期：1992.3

  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.
• Cu(I)–NHC Catalyzed Asymmetric Silyl Transfer to Unsaturated Lactams and Amides
  作者：Vittorio Pace、James P. Rae、David J. Procter

  DOI：10.1021/ol4033623

  日期：2014.1.17

  The first asymmetric silylation of unsaturated lactams and amides using Cu(I)-NHC catalysts and PhMe(2)SiBpin has been accomplished. The method has been exploited in an expedient asymmetric synthesis of the (R)-enantiomer of the nootropic drug oxiracetam.