(1R,2R)-N-((S)-樟脑-10-磺酰基)-DPEN | 637357-55-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: (1R,2R)-N-((S)-樟脑-10-磺酰基)-DPEN
• 英文名称: (1R,2R)-N-((S)-camphor-10-sulfonyl)-1,2-diphenylethylenediamine
• 英文别名: (1R,2R)-N-((S)-camphor-10-sulfonyl)-DPEN；N-[(1S,4R)-10-Camphorsulphonyl]-(1R, 2R)-1, 2-diphenylethylenediamine；N-[(1R,2R)-2-amino-1,2-diphenylethyl]-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 637357-55-2
• 化学式: C₂₄H₃₀N₂O₃S
• 分子量: 426.58
• InChiKey: ITNLZZDQOMWQDT-VDEHWKIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  97.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [RhCl2(p-cymene)]2 、 (1R,2R)-N-((S)-樟脑-10-磺酰基)-DPEN 在 三乙胺 、 异丙醇 作用下， 反应 3.0h， 以43%的产率得到[RuCl(η⁶-p-cymene)(1R,2R)-N-((1S,2S)-borneol-10-sulfonyl)-1,2-diphenylethylenediamine]
  参考文献：
  名称：

  Asymmetric transfer hydrogenation of 1-phenyl dihydroisoquinolines using Ru(II) diamine catalysts

  摘要：

  A new [Ru(II)(eta(6)-p-cymene)(1R,2R)-N-((1S,2S)-borneol-10-sulfonyl)-1,2-diphenylethylenediamine] catalyst for the asymmetric transfer hydrogenation of both 1-alkyl and 1-aryl dihydroisoquinolines has been isolated. For the first time in this type of reaction, the catalyst employs an N-alkylsulfonyl group instead of N-arylsulfonyl. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2013.03.004
• 作为产物：
  描述：

  D(+)-10-樟脑磺酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 (1R,2R)-N-((S)-樟脑-10-磺酰基)-DPEN
  参考文献：
  名称：

  The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol

  摘要：

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.04.017
• 作为试剂：
  描述：

  4'-氯-2,2,2-三氟苯乙酮 在 (1R,2R)-N-((S)-樟脑-10-磺酰基)-DPEN 、 三乙酰氧基硼氢化钠 、 溶剂黄146 、 苯甲酸 作用下， 以 环己烷 为溶剂， 反应 144.0h， 生成 、 、 、
  参考文献：
  名称：

  烯酮与芳基三氟甲基酮的有机催化非对映和对映选择性氧杂-杂-狄尔斯-阿尔德反应合成三氟甲基取代的四氢吡喃

  摘要：

  四氢吡喃衍生物存在于生物活性物质中，将三氟甲基基团引入分子中通常会改善生物功能。在这里，我们报告了由胺基催化剂体系催化的非对映和对映选择性氧杂-杂-Diels-Alder 反应，该催化剂体系提供三氟甲基取代的四氢吡喃酮。确定了适用于反应的催化剂体系和条件，以提供具有高对映选择性的所需非对映体产物，并合成了各种具有高非对映选择性和对映选择性的三氟甲基取代的四氢吡喃酮。机理研究表明，该反应涉及[4 + 2]环加成途径，其中烯酮的烯胺充当二烯，芳基三氟甲基酮的酮羰基充当亲二烯体。在这项研究中，

  DOI：

  10.1039/d1ob01844b

文献信息

• The Ru-catalyzed enantioselective preparation of chiral halohydrins and their application in the synthesis of (R)-clorprenaline and (S)-sotalol
  作者：Chuanjun Lu、Zonghua Luo、Ling Huang、Xingshu Li

  DOI：10.1016/j.tetasy.2011.04.017

  日期：2011.4

  The asymmetric transfer hydrogenation of a series of halo-substituted aryl methyl ketones, including those substituted in both alpha-methyl and aryl rings, was studied for the preparation of chiral halohydrins. Up to 99.7% ee was obtained with 2-chloro-1-(2-chlorophenyl)ethanone as the substrate and Ru-CsDPEN as the catalyst in an HCOONa/H2O system. (R)-Clorprenaline, a drug used in the treatment of respiratory disorders, such as bronchitis and asthma, and (S)-sotalol, a class-III antiarrhythmic compound, were prepared with these chiral halohydrins. (C) 2011 Elsevier Ltd. All rights reserved.
• Organocatalytic diastereo- and enantioselective oxa-hetero-Diels–Alder reactions of enones with aryl trifluoromethyl ketones for the synthesis of trifluoromethyl-substituted tetrahydropyrans
  作者：Maira Pasha、Fujie Tanaka

  DOI：10.1039/d1ob01844b

  日期：——

  high diastereo- and enantioselectivities. Mechanistic investigation suggested that the reactions involve a [4 + 2] cycloaddition pathway, in which the enamine of the enone acts as the diene and the ketone carbonyl group of the aryl trifluoromethyl ketone acts as the dienophile. In this study, tetrahydropyran derivatives with the desired stereochemistry that are difficult to synthesize by previously reported

  四氢吡喃衍生物存在于生物活性物质中，将三氟甲基基团引入分子中通常会改善生物功能。在这里，我们报告了由胺基催化剂体系催化的非对映和对映选择性氧杂-杂-Diels-Alder 反应，该催化剂体系提供三氟甲基取代的四氢吡喃酮。确定了适用于反应的催化剂体系和条件，以提供具有高对映选择性的所需非对映体产物，并合成了各种具有高非对映选择性和对映选择性的三氟甲基取代的四氢吡喃酮。机理研究表明，该反应涉及[4 + 2]环加成途径，其中烯酮的烯胺充当二烯，芳基三氟甲基酮的酮羰基充当亲二烯体。在这项研究中，
• Asymmetric transfer hydrogenation of 1-phenyl dihydroisoquinolines using Ru(II) diamine catalysts
  作者：Jan Přech、Jiří Václavík、Petr Šot、Jan Pecháček、Beáta Vilhanová、Jakub Januščák、Kamila Syslová、Richard Pažout、Jaroslav Maixner、Jakub Zápal、Marek Kuzma、Petr Kačer

  DOI：10.1016/j.catcom.2013.03.004

  日期：2013.6

  A new [Ru(II)(eta(6)-p-cymene)(1R,2R)-N-((1S,2S)-borneol-10-sulfonyl)-1,2-diphenylethylenediamine] catalyst for the asymmetric transfer hydrogenation of both 1-alkyl and 1-aryl dihydroisoquinolines has been isolated. For the first time in this type of reaction, the catalyst employs an N-alkylsulfonyl group instead of N-arylsulfonyl. (c) 2013 Elsevier B.V. All rights reserved.