N-(1R,2R)-(2-aminocyclohexyl)-4-methoxy-benzenesulfonamide | 1047662-99-6

• 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: N-(1R,2R)-(2-aminocyclohexyl)-4-methoxy-benzenesulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-4-methoxybenzenesulfonamide
• CAS: 1047662-99-6
• 化学式: C₁₃H₂₀N₂O₃S
• 分子量: 284.379
• InChiKey: JNFMKWFWIKFICZ-CHWSQXEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  89.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(1R,2R)-(2-aminocyclohexyl)-4-methoxy-benzenesulfonamide 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 48.0h， 生成 (1S,2R,4R,1'R,2'R)-N-{trans-2'-[2-hydroxy-7,7-dimethylbicyclo[2.2.1]hept-1-ylmethylsulfonamino]cyclohexyl}-4''-methoxybenzenesulfonamide
  参考文献：
  名称：

  反式-1-芳烃磺酰基-氨基-2-异冰片磺酰基磺酰基氨基环己烷催化的手性叔醇催化酮类有机锌的加成反应

  摘要：

  使用四异丙醇钛和衍生自1-芳烃磺酰基氨基-2-异冰片醇磺酰胺基环己烷的手性配体，将不同的有机锌试剂（例如烷基）或原位生成的芳基，烯丙基，烯基和炔基衍生物催化对映选择性加成到简单的芳基酮上，得到对映选择性最高> 99％的相应叔醇。描述了一种合成所用二磺酰胺配体的简单有效的方法。

  DOI：

  10.1016/j.tetasy.2005.08.031
• 作为产物：
  描述：

  对甲氧基苯磺酰氯 、 (R,R)-1,2-diaminocyclohexane tartrate 在 sodium hydroxide 、 三乙胺 作用下， 以80%的产率得到N-(1R,2R)-(2-aminocyclohexyl)-4-methoxy-benzenesulfonamide
  参考文献：
  名称：

  Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane

  摘要：

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.04.036

文献信息

• Chiral tertiary alcohols from a trans-1-arenesulfonyl-amino-2-isoborneolsulfonylaminocyclohexane-catalyzed addition of organozincs to ketones
  作者：Vicente J. Forrat、Diego J. Ramón、Miguel Yus

  DOI：10.1016/j.tetasy.2005.08.031

  日期：2005.10

  enantioselective addition of different organozinc reagents, such as alkyl, or in situ generated aryl, allyl, alkenyl and alkynyl derivatives to simple aryl ketones, was accomplished using titanium tetraisopropoxide and chiral ligands derived from 1-arenesulfonylamino-2-isoborneolsulfonylamidocyclohexane, giving the corresponding tertiary alcohols with enantioselectivities up to >99%. A simple and efficient

  使用四异丙醇钛和衍生自1-芳烃磺酰基氨基-2-异冰片醇磺酰胺基环己烷的手性配体，将不同的有机锌试剂（例如烷基）或原位生成的芳基，烯丙基，烯基和炔基衍生物催化对映选择性加成到简单的芳基酮上，得到对映选择性最高> 99％的相应叔醇。描述了一种合成所用二磺酰胺配体的简单有效的方法。
• Auxiliary‐Free Remote Dearomatizative Nitrenoid Transfer for Enantioselective Construction of Spirolactams
  作者：Bo‐Han Zhu、Wen‐Ting Guo、Qing Sun、Peng‐Cheng Qian、Long‐Wu Ye、Long Li

  DOI：10.1002/adsc.202101189

  日期：2022.1.18

  An Ir-catalyzed remote dearomatizative amidation for the enantioselective construction of chiral spirolactams in 70–93% yield with 81–96% ee was developed. This protocol represented a more atom-economical approach to chiral spirolactams via Ir-catalyzed nitrenoid transfer without the introduction of a traceless O-silyl achiral auxiliary.

  开发了一种 Ir 催化的远程脱芳构酰胺化，用于手性螺内酰胺的对映选择性构建，产率为 70-93%，ee 为 81-96%。该协议代表了一种更原子经济的手性螺内酰胺方法，通过 Ir 催化的 nitrenoid 转移而无需引入无痕 O-甲硅烷基非手性助剂。
• Ruthenium(II) and rhodium(III) catalyzed asymmetric transfer hydrogenation (ATH) of acetophenone in isopropanol and in aqueous sodium formate using new chiral substituted aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane
  作者：Norma A. Cortez、Gerardo Aguirre、Miguel Parra-Hake、Ratnasamy Somanathan

  DOI：10.1016/j.tetasy.2008.04.036

  日期：2008.6

  A series of aromatic monosulfonamide ligands derived from (1R,2R)-diaminocyclohexane were synthesized with electron withdrawing and donating groups. These were complexed with Rh(Cp*) or Ru(arene) and their catalytic efficiencies were compared in the ATH of acetophenone using sodium formate/water or isopropanol/KOH as the hydrogen source. Results suggest that substituents on the benzene ring of the sulfonamide have very little electronic impact on the enantioselectivity and mechanism of the reaction. (C) 2008 Elsevier Ltd. All rights reserved.
• trans-1-Sulfonylamino-2-isoborneolsulfonylaminocyclohexane Derivatives: Excellent Chiral Ligands for the Catalytic Enantioselective Addition of Organozinc Reagents to Ketones
  作者：Vicente J. Forrat、Oscar Prieto、Diego J. Ramón、Miguel Yus

  DOI：10.1002/chem.200501397

  日期：2006.5.24

  The catalytic enantioselective addition of different organozinc reagents (such as alkyl and aryl derivatives or in situ generated aryl, allyl alkenyl, and alkynyl derivatives obtained through different transmetallation processes) to simple ketones has been accomplished by using titanium tetraisopropoxide and chiral ligands derived from substituted trans-1-sulfonylamino-2-isoborneolsulfonylaminocyclohexane

  通过使用四异丙氧基钛和衍生自取代的反式-1-磺酰基氨基-2-异冰片醇磺酰基氨基环己烷，生成相应的叔醇，对映体过量（ee）最高> 99％。描述了一种简单有效的合成这些反应中使用的手性配体的方法。