N-Ts-3,5-dimethoxybenzamide | 519150-72-2

• 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: N-Ts-3,5-dimethoxybenzamide
• 英文别名: 3,5-dimethoxy-N-(4-methylphenyl)sulfonylbenzamide
• CAS: 519150-72-2
• 化学式: C₁₆H₁₇NO₅S
• 分子量: 335.381
• InChiKey: HPEVXOCYJXVLSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  重氮乙酸乙酯 、 N-Ts-3,5-dimethoxybenzamide 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper(II) acetate monohydrate 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以45%的产率得到3-ethoxycarbonyl-3-ethoxycarbonylmethyl-4,6-dimethoxy-2-tosylisoindolin-1-one
  参考文献：
  名称：

  Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides

  摘要：

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [{RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.08.095
• 作为产物：
  描述：

  对甲基苯磺酰异氰酸酯 、 3,5-二甲氧基苯甲酸 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到N-Ts-3,5-dimethoxybenzamide
  参考文献：
  名称：

  N-TS-苯甲酰胺和1,3-二烯的Pd催化不对称合成3,4-二氢异喹啉酮

  摘要：

  已经开发了一种Pd（II）催化的N -Ts-苯甲酰胺与1,3-二烯的不对称氧化环合反应，使用手性吡啶-恶唑啉型配体进行手性3,4-二氢异喹啉酮的区域和立体选择性合成。

  DOI：

  10.1002/bkcs.12227

文献信息

• Rhodium catalyzed C–H olefination of N-benzoylsulfonamides with internal alkenes
  作者：Chen Zhu、John R. Falck

  DOI：10.1039/c2cc16963k

  日期：——

  An annulation via tandem rhodium catalyzed C–H olefination of N-benzoylsulfonamides with internal olefins followed by C–N bond formation is disclosed. A N-substituted quaternary center is formed during the reaction thus providing efficient access to a series of 3,3-disubstituted isoindolinones.

  通过双重铑催化的C–H烯化反应，将N-苯酰磺酰胺与内部烯烃进行环化，接着形成C–N键。这一反应过程中形成了N-取代的四价中心，从而高效地合成了一系列3,3-二取代的异吲哚啉酮。
• <i>N</i>-Acylsulfonamide Assisted Tandem C−H Olefination/Annulation: Synthesis of Isoindolinones
  作者：Chen Zhu、J. R. Falck

  DOI：10.1021/ol200093f

  日期：2011.3.4

  A tandem C-H olefination/annulation sequence directed by N-acylsulfonamides affords a variety of isoindolinones. This transformation is compatible with aliphatic alkenes as well as conjugated alkenes. Notably, molecular oxygen can be used as the sole, eco-friendly oxidant.
• <scp>Pd‐Catalyzed</scp> Asymmetric Synthesis of 3, <scp>4‐Dihydroisoquinolinones</scp> From <scp> <i>N</i> ‐Ts‐Benzamides </scp> and 1, <scp>3‐Dienes</scp>
  作者：Tae Kyun Kim、So Won Youn

  DOI：10.1002/bkcs.12227

  日期：2021.3

  A Pd(II)‐catalyzed asymmetric oxidative annulation of N‐Ts‐benzamides with 1,3‐dienes using a chiral pyridine‐oxazoline‐type ligand for the regio‐ and stereoselective synthesis of chiral 3,4‐dihydroisoquinolinones has been developed.

  已经开发了一种Pd（II）催化的N -Ts-苯甲酰胺与1,3-二烯的不对称氧化环合反应，使用手性吡啶-恶唑啉型配体进行手性3,4-二氢异喹啉酮的区域和立体选择性合成。
• Rhodium catalyzed synthesis of isoindolinones via C–H activation of N-benzoylsulfonamides
  作者：Chen Zhu、John R. Falck

  DOI：10.1016/j.tet.2012.08.095

  日期：2012.11

  An efficient approach to a wide range of isoindolinones, including 3-monosubstituted and 3,3-disubstituted isoindolinones, from the annulation of N-benzoylsulfonamides with olefins and diazoacetate has been developed. The transformation is broadly compatible with both terminal and internal olefins. Moreover, diazoacetate is for the first time incorporated into an amide-directed C-H functionalization reaction. Specifically, the rhodium complex [RhCl2Cp*}2] enables the in situ dimerization of diazoacetate in addition to its role in catalyzing C-H functionalization/cross-coupling. (C) 2012 Elsevier Ltd. All rights reserved.