N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)-4-methylbenzenesulfonamide | 1220123-26-1

• 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-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)-4-methylbenzenesulfonamide
• 英文别名: N-((1S,3R)-3-amino2,2,3-trimethylciclopentyl)-4-methylbenzenesulfonamide；N-[(1S,3R)-3-amino-2,2,3-trimethylcyclopentyl]-4-methylbenzenesulfonamide
• CAS: 1220123-26-1
• 化学式: C₁₅H₂₄N₂O₂S
• 分子量: 296.434
• InChiKey: GSMQJJVLEKEJKE-DZGCQCFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)-4-methylbenzenesulfonamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以87%的产率得到RuCl[κ²(N,N')-(1S,3R)-N-(3-amino-2,2,3-trimethylcyclopentyl)-4-methylbenzenesulfonamide](η⁶-p-cymene)
  参考文献：
  名称：

  Synthesis and characterization of Ru(II) and Ir(III) complexes that bear camphoric 1,3-diamine ligands

  摘要：

  Two rigid N-monosulfonylated 1,3-diamine ligands have been prepared starting from commercially available D-camphor through three steps. Their reactions with [Ru(eta(6)-arene)(mu-Cl)Cl](2) (arene = p-cymene or C6H5CO2Et) or [Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) afforded five new complexes. The structures of one monosulfonamide 1,3-diamine ligand and three organometallic complexes were confirmed by X-ray crystallography. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2014.06.017
• 作为产物：
  描述：

  D-樟脑酸 在 sodium azide 、 硫酸 作用下， 以 乙醇 、 氯仿 为溶剂， 生成 N-((1S,3R)-3-amino-2,2,3-trimethylcyclopentyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  (+)-樟脑酸衍生的新型双功能 1,3-二胺有机催化剂用于 1,3-二羰基化合物与硝基烯烃的不对称迈克尔加成

  摘要：

  新型 1,3-二胺衍生的双功能硫脲和方酰胺有机催化剂由 (+)-樟脑酸合成。这些催化剂很容易在多达两到五个合成步骤中获得，采用一种灵活的方法，有助于它们的结构变化。在 1,3-二羰基化合物与几种反式-β-硝基苯乙烯的不对称迈克尔加成中检查了它们的催化活性。在这些反应中获得了高达 98% 的产率和高达 74% 的对映体过量和高非对映选择性（dr高达 93:7），表明 1,3-二胺衍生的双功能硫脲是有效的有机催化剂。

  DOI：

  10.1002/chir.23424

文献信息

• Enantioselective ethylation of aldehydes with 1,3-N-donor ligands derived from (+)-camphoric acid
  作者：Dina Murtinho、M. Elisa Silva Serra、A.M.d’A. Rocha Gonsalves

  DOI：10.1016/j.tetasy.2009.12.012

  日期：2010.1

  Derivatives of (+)-camphoric acid were prepared by a short and simple synthetic sequence and proved to be excellent ligands for the enantioselective ethylation of benzaldellyde with diethylzinc, with ees of up to 96% being obtained The most efficient ligand was tested with several aromatic alclehydes and ees of up to 99% were observed Structural features of the ligands are determinant for achieving high enantioselectivities. (c) 2009 Elsevier Ltd All rights reserved
• Synthesis and characterization of Ru(II) and Ir(III) complexes that bear camphoric 1,3-diamine ligands
  作者：Jun-Lai Yu、Rong Guo、Hui Wang、Zhan-Ting Li、Dan-Wei Zhang

  DOI：10.1016/j.jorganchem.2014.06.017

  日期：2014.10

  Two rigid N-monosulfonylated 1,3-diamine ligands have been prepared starting from commercially available D-camphor through three steps. Their reactions with [Ru(eta(6)-arene)(mu-Cl)Cl](2) (arene = p-cymene or C6H5CO2Et) or [Ir(eta(5)-C5Me5)(mu-Cl)Cl](2) afforded five new complexes. The structures of one monosulfonamide 1,3-diamine ligand and three organometallic complexes were confirmed by X-ray crystallography. (C) 2014 Elsevier B.V. All rights reserved.
• New bifunctional 1,3‐diamine organocatalysts derived from (+)‐camphoric acid for asymmetric Michael addition of 1,3‐dicarbonyl compounds to nitroolefins
  作者：Márcia Rénio、Dina Murtinho、M. Rita Ventura

  DOI：10.1002/chir.23424

  日期：2022.5

  Novel 1,3-diamine-derived bifunctional thiourea and squaramide organocatalysts were synthesized from (+)-camphoric acid. These catalysts were easily obtained in up to two to five synthetic steps, in a flexible approach that facilitates their structure variation. Their catalytic activity was examined in the asymmetric Michael addition of 1,3-dicarbonyl compounds to several trans-β-nitrostyrenes. Yields

  新型 1,3-二胺衍生的双功能硫脲和方酰胺有机催化剂由 (+)-樟脑酸合成。这些催化剂很容易在多达两到五个合成步骤中获得，采用一种灵活的方法，有助于它们的结构变化。在 1,3-二羰基化合物与几种反式-β-硝基苯乙烯的不对称迈克尔加成中检查了它们的催化活性。在这些反应中获得了高达 98% 的产率和高达 74% 的对映体过量和高非对映选择性（dr高达 93:7），表明 1,3-二胺衍生的双功能硫脲是有效的有机催化剂。