N-环庚-2-烯-1-基-4-甲基苯磺酰胺 | 97399-11-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-环庚-2-烯-1-基-4-甲基苯磺酰胺
• 英文名称: 1-[N-(p-toluenesulfonyl)amino]cyclohept-2-en
• 英文别名: N-cyclohept-2-enyl-N-tosylamide；Benzenesulfonamide, N-2-cyclohepten-1-yl-4-methyl-；N-cyclohept-2-en-1-yl-4-methylbenzenesulfonamide
• CAS: 97399-11-6
• 化学式: C₁₄H₁₉NO₂S
• 分子量: 265.376
• InChiKey: NKZNWZAOYBRBSC-UHFFFAOYSA-N

物化性质

• 沸点：
  401.7±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 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-环庚-2-烯-1-基-4-甲基苯磺酰胺 在 Grubbs catalyst first generation sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 20.0~40.0 ℃ 、101.33 kPa 条件下， 反应 1.0h， 生成 2-hex-5-enyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrole
  参考文献：
  名称：

  ROM-RCM of cycloalkene-yne

  摘要：

  Ring-opening metathesis and ring-closing metathesis (ROM-RCM) of cycloalkene-yne was demonstrated using a first- or second-generation ruthenium complex. When cycloalkenes bearing the alkyne part at the C-3 position were reacted with a first-generation ruthenium-carbene complex under an atmosphere of ethylene, ROM-RCM proceeded smoothly to give skeletal reorganized products in good yields. In this reaction, cycloalkene-ynes having terminal alkyne were suitable. On the other hand, when cycloalkenes bearing the alkyne part at the C-1 position were treated with a second-generation ruthenium-carbene complex, ROM-RCM proceeded smoothly to give bicyclic compounds and/or dimeric compounds in good yields. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.05.030
• 作为产物：
  描述：

  2-cycloheptenyl acetate 、 sodium p-toluenesulfonamide 在 四(三苯基膦)钯 1,2-双(二苯基膦)乙烷 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 21.0h， 以73%的产率得到N-环庚-2-烯-1-基-4-甲基苯磺酰胺
  参考文献：
  名称：

  Synthesis of protected allylamines via palladium-catalyzed amide addition to allylic substrates

  摘要：

  DOI：

  10.1016/s0040-4039(00)98329-1

文献信息

• PROCESS FOR PREPARING AMINO COMPOUNDS BY USING SALEN-MANGANESE COMPLEXES AS THE CATALYST
  申请人：JAPAN SCIENCE AND TECHNOLOGY CORPORATION

  公开号：EP1375478A1

  公开（公告）日：2004-01-02

  Disclosed is a process for the enantioselective production of an optically active amino compound by the amination of the C-H bond of an organic compound. The amino compound is produced by converting the C-H bond at the allyl position of an alkene or the C-H bond at the benzyl position of an alkylarene to the corresponding C-N bond, using a salen-manganese complex as the catalyst and N-substituted iminoaryliodinane as the amination agent. Both the catalytic activity and the enantioselectivity are very high when there is used a catalyst in which the 3- and 5- positions of the salicylaldehyde moiety of the salen ligand are substituted with an electron-withdrawing group, particularly with a halogen atom.

  本发明公开了一种通过胺化有机化合物的 C-H 键来对映选择性生产光学活性氨基化合物的工艺。该氨基化合物是通过将烯的烯丙基位上的 C-H 键或烷烃的苄基位上的 C-H 键转化为相应的 C-N 键而制得的，使用的催化剂是柳锰络合物，胺化剂是 N-取代的亚氨基芳基碘烷。当使用的催化剂中水杨醛配位体的 3-和 5-位被抽电子基团（特别是卤原子）取代时，催化活性和对映体选择性都非常高。
• Process for preparing amino compounds by using salen-manganese complexes as the catalyst
  申请人：——

  公开号：US20030139627A1

  公开（公告）日：2003-07-24

  Disclosed is a process for the enantioselective production of an optically active amino compound by the amination of the C—H bond of an organic compound. The amino compound is produced by converting the C—H bond at the allyl position of an alkene or the C—H bond at the benzyl position of an alkylarene to the corresponding C—N bond, using a salen-manganese complex as the catalyst and N-substituted iminoaryliodinane as the amination agent. Both the catalytic activity and the enantioselectivity are very high when there is used a catalyst in which the 3- and 5-positions of the salicylaldehyde moiety of the salen ligand are substituted with an electron-withdrawing group, particularly with a halogen atom.

  本发明公开了一种通过胺化有机化合物的 C-H 键来对映选择性生产光学活性氨基化合物的工艺。该氨基化合物是通过将烯的烯丙基位上的 C-H 键或烷烃的苄基位上的 C-H 键转化为相应的 C-N 键来生产的，使用的催化剂是柳锰络合物，胺化剂是 N-取代的亚氨基芳基碘烷。如果使用的催化剂中水杨醛配位体的 3 位和 5 位被抽电子基团（特别是卤原子）取代，则催化活性和对映体选择性都非常高。
• <i>t</i>-BuOK-Mediated Iodoaziridination Reaction of <i>N</i>-Allylic Tosylamide Derivatives
  作者：Osamu Kitagawa、Takashi Suzuki、Takeo Taguchi

  DOI：10.1021/jo980371m

  日期：1998.7.1
• Mn(salen)-catalyzed enantioselective CH amination
  作者：Yoshinori Kohmura、Tsutomu Katsuki

  DOI：10.1016/s0040-4039(01)00427-0

  日期：2001.5

  A chiral 3.3',5,5'-tetrabromosubstituted (salen)manganese(III) complex was found to be an efficient catalyst for asymmetric Cn amination (up to 89% ee). In the reaction of cycloalkenes, allylic amination occurred in preference to aziridination, (C) 2001 Elsevier Science Ltd. All rights reserved.
• BYSTROEM, S. E.;ASLANIAN, R.;BAECKVALL, J. -E., TETRAHEDRON LETT., 1985, 26, N 14, 1749-1752
  作者：BYSTROEM, S. E.、ASLANIAN, R.、BAECKVALL, J. -E.

  DOI：——

  日期：——