N-deca-2,3-dienyl p-toluenesulfonamide | 581075-47-0

• 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-deca-2,3-dienyl p-toluenesulfonamide
• 英文别名: N-(2,3-decadienyl)toluenesulfonamide；N-(2,3-decadienyl) p-toluenesulfonamide
• CAS: 581075-47-0
• 化学式: C₁₇H₂₅NO₂S
• 分子量: 307.457
• InChiKey: GFJUZTMHHUBOTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  435.3±48.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-deca-2,3-dienyl p-toluenesulfonamide 在 silver hexafluoroantimonate 、 chlorobis(ethylene)rhodium(I) dimer 、 碳酸氢钠 、 间氯过氧苯甲酸 、 三苯基膦 、 (-)-1,2-双((2R,5R)-2,5-二苯基膦)乙烷 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 39.34h， 生成
  参考文献：
  名称：

  基于Rh的动力学分辨率的对映选择性[4 + 2]-环加成反应-Allene-1,3-二烯的异构化

  摘要：

  已经开发出Rh催化的涉及分子内[4 + 2]-环加成反应的1,3-二取代的allen-1,3-二烯的动力学拆分。随后进行C = C异构化反应，最终得到具有很高对映体和E选择性的氮杂[4.3.0]双环化合物。通过仔细的控制实验揭示了该机制。还证实了高度对映体富集的双环产物的合成潜力。

  DOI：

  10.1002/cjoc.202000659
• 作为产物：
  描述：

  deca-2,3-dien-1-ol 在 吡啶 、 三溴化磷 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 13.0h， 生成 N-deca-2,3-dienyl p-toluenesulfonamide
  参考文献：
  名称：

  Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides

  摘要：

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.

  DOI：

  10.1021/jo0342469

文献信息

• Rhodium‐Catalyzed Dynamic Kinetic [4+2] Cycloaddition of Allene‐1,3‐Dienes
  作者：Yulin Han、Anni Qin、Qian Zhang、Xue Zhang、Hui Qian、Shengming Ma

  DOI：10.1002/anie.202211635

  日期：2022.11.21

  A rhodium/Malphos catalytic recipe has been developed for the dynamic kinetic intramolecular Diels–Alder cycloaddition of allene-1,3-dienes. The desired cis-fused [4.3.0]bicyclic products were obtained with decent yields and excellent stereo- and enantioselectivity. Its dynamic kinetic nature has been confirmed by careful mechanistic studies.

  已经开发了一种铑/Malphos 催化配方，用于丙二烯-1,3-二烯的动态动力学分子内 Diels-Alder 环加成。获得了所需的顺式稠合 [4.3.0] 双环产物，具有良好的收率和出色的立体选择性和对映选择性。其动态动力学性质已通过仔细的机理研究得到证实。
• <scp>Rh‐Catalyzed</scp>Kinetic<scp>Resolution‐Based</scp>Enantioselective [4+2]‐<scp>Cycloaddition‐Isomerization</scp>of Allene‐1,3‐dienes
  作者：Anni Qin、Qian Zhang、Hui Qian、Yulin Han、Shengming Ma

  DOI：10.1002/cjoc.202000659

  日期：2021.3

  The first example of Rh‐catalyzed kinetic resolution of 1,3‐disubstituted allene‐1,3‐dienes involving intramolecular [4+2]‐cycloaddition has been developed. Followed by C=C isomerization, the reaction finally afforded aza‐[4.3.0]bicyclic compounds with a very high enantio‐ and E‐selectivity. The mechanism has been unveiled by careful control experiments. The synthetic potentials of highly enantioenriched

  已经开发出Rh催化的涉及分子内[4 + 2]-环加成反应的1,3-二取代的allen-1,3-二烯的动力学拆分。随后进行C = C异构化反应，最终得到具有很高对映体和E选择性的氮杂[4.3.0]双环化合物。通过仔细的控制实验揭示了该机制。还证实了高度对映体富集的双环产物的合成潜力。
• Studies on Pd(II)-Catalyzed Coupling−Cyclization of α- or β-Amino Allenes with Allylic Halides
  作者：Shengming Ma、Fei Yu、Wenzhong Gao

  DOI：10.1021/jo0342469

  日期：2003.7.1

  The palladium-catalyzed coupling-cyclization of alpha- or beta-amino allenes with allylic halides leading to 3-allylic 2,5-dihydropyrroles and 1,2,3,6-tetrahydropyridines, respectively, was studied. The starting materials are easily available. The skeletons of both two classes of products were established by the X-ray diffraction studies of 7i and 9b. Through the study of the reaction of 2b with 3-chloro-1-butene, 1-chloro-2-butene, and pi-allyl palladium species and the stereochemical outcome of the coupling cyclization of (S)-2m and (R)-2n, it is believed that the current transformation most likely proceeded via a Pd(II)-catalyzed pathway, although a Pd(0) pathway cannot be completely excluded.