(1S,2R)-2-nitro-1-(p-tolyl)propylcarbamic acid tert-butyl ester | 1001022-97-4

• 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: (1S,2R)-2-nitro-1-(p-tolyl)propylcarbamic acid tert-butyl ester
• 英文别名: tert-butyl (1S,2R)-2-nitro-1-p-tolylpropylcarbamate；(1S,2R)-1-(4-methylphenyl)-2-nitropropyl-carbamic acid tert-butyl ester；tert-butyl N-[(1S,2R)-1-(4-methylphenyl)-2-nitropropyl]carbamate
• CAS: 1001022-97-4
• 化学式: C₁₅H₂₂N₂O₄
• 分子量: 294.351
• InChiKey: JYCOFQQORURYOU-DGCLKSJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  硝基乙烷 、 4-methylbenzaldehyde N-(tert-butoxycarbonyl)imine 在 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(2S)-1-[[[[(2S)-2-[[3,5-bis(trifluoromethyl)phenyl]carbamothioylamino]-3-phenylpropyl]amino]-pyrrolidin-1-ium-1-ylidenemethyl]amino]-3-phenylpropan-2-yl]thiourea;chloride 、 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以89%的产率得到(1S,2R)-2-nitro-1-(p-tolyl)propylcarbamic acid tert-butyl ester
  参考文献：
  名称：

  与无环胍-硫脲双功能有机催化剂的对映选择性氮杂-亨利反应

  摘要：

  Abstractmagnified imageA highly enantioselective aza‐Henry reaction of imines with nitromethane was achieved with a reactive guanidine‐thiourea bifunctional organocatalyst affording β‐nitroamines with high enantioselectivity (up to 96% ee). The diastereo‐ and enantioselective version of this reaction with nitroalkanes also proceeded selectively (up to 99:1 dr with 99% ee).

  DOI：

  10.1002/adsc.200800692

文献信息

• Enantioselective Aza-Henry Reaction with an <i>N</i>-Sulfinyl Urea Organocatalyst
  作者：MaryAnn T. Robak、Monica Trincado、Jonathan A. Ellman

  DOI：10.1021/ja075653v

  日期：2007.12.1

  simultaneously acidify the urea and provide asymmetric induction in hydrogen-bond-catalyzed reactions. The utility of this new catalyst structure is demonstrated by the high selectivity provided in the aza-Henry reaction not only for aromatic N-Boc imine substrates but also for aliphatic imines for which enantioselective H-bonding catalysis has not previously been demonstrated.

  已经开发出一类新的有机催化剂，它结合了亚磺酰基作为脲或硫脲取代基。亚磺酰基同时用于酸化尿素并在氢键催化反应中提供不对称诱导。这种新催化剂结构的实用性通过 aza-Henry 反应提供的高选择性得到证明，不仅对芳香族 N-Boc 亚胺底物，而且对脂肪族亚胺（之前尚未证明对映选择性氢键催化）。
• Catalytic Asymmetric Nitro-Mannich Reactions with a Yb/K Heterobimetallic Catalyst
  作者：Tatsuya Nitabaru、Naoya Kumagai、Masakatsu Shibasaki

  DOI：10.3390/molecules15031280

  日期：——

  A catalytic asymmetric nitro-Mannich (aza-Henry) reaction with rare earth metal/alkali metal heterobimetallic catalysts is described. A Yb/K heterobimetallic catalyst assembled by an amide-based ligand promoted the asymmetric nitro-Mannich reaction to afford enantioenriched anti-b-nitroamines in up to 86% ee. Facile reduction of the nitro functionality allowed for efficient access to optically active

  描述了与稀土金属/碱金属异双金属催化剂的催化不对称硝基-曼尼希 (氮杂-亨利) 反应。由基于酰胺的配体组装的 Yb/K 杂双金属催化剂促进了不对称硝基-曼尼希反应，以提供高达 86% ee 的对映体富集的抗 b-硝基胺。硝基官能团的轻松还原允许有效获取光学活性 1,2-二胺。
• Asymmetric aza-Henry reaction of BOC-protected imines with zinc-FAM catalyst
  作者：Nurzhan Beksultanova、Özdemir Doğan

  DOI：10.1080/00397911.2024.2303054

  日期：2024.3.3

  Derivatives of ferrocenyl-substituted aziridinyl methanol (FAM) ligands were used with zinc metal for asymmetric aza-Henry (nitro-aldol) reaction of N-Boc protected imines with nitroalkanes. At opt...

  二茂铁基取代的氮丙啶基甲醇 (FAM) 配体的衍生物与锌金属一起用于 N-Boc 保护的亚胺与硝基烷烃的不对称氮杂亨利（硝基醇醛）反应。在选择...
• Highly Enantioselective Thiourea-Catalyzed Nitro-Mannich Reactions
  作者：Tehshik P. Yoon、Eric N. Jacobsen

  DOI：10.1002/anie.200461814

  日期：2005.1.7
• <i>syn</i>-Selective Catalytic Asymmetric Nitro-Mannich Reactions Using a Heterobimetallic Cu−Sm−Schiff Base Complex
  作者：Shinya Handa、Vijay Gnanadesikan、Shigeki Matsunaga、Masakatsu Shibasaki

  DOI：10.1021/ja0701560

  日期：2007.4.1

  syn-Selective catalytic asymmetric nitro-Mannich reactions using a heterobimetallic Cu/Sm/Schiff base complex are described. The present method is complementary to the previously reported methods, and products were obtained in high syn-selectivity (> 20:1), yield (99-62%), and enantioselectivity (98-83% ee). Both Cu and Sm metals, aligned suitably in a dinucleating Schiff base ligand, were essential to realize high synselectivity.