N-[(1R,2R)-2-氨基环己基]-3,5-双(三氟甲基)苯亚磺酰胺 | 1233703-68-8

• 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-[(1R,2R)-2-氨基环己基]-3,5-双(三氟甲基)苯亚磺酰胺
• 英文名称: N-((1R,2R)-2-aminocyclohexyl)-3,5-bis(trifluoromethyl)benzenesulfonamide
• 英文别名: N-[(1R,2R)-2-aminocyclohexyl]-3,5-bis(trifluoromethyl)benzenesulfonamide
• CAS: 1233703-68-8
• 化学式: C₁₄H₁₆F₆N₂O₂S
• 分子量: 390.35
• InChiKey: JBCNCYCPWLJXDO-VXGBXAGGSA-N

物化性质

• 沸点：
  400.7±55.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  80.6
• 氢给体数：
  2
• 氢受体数：
  10

安全信息

• 储存条件：
  2-8°C

反应信息

• 作为反应物：
  描述：

  N-[(1R,2R)-2-氨基环己基]-3,5-双(三氟甲基)苯亚磺酰胺 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 24.75h， 生成 (2R)-2-amino-N-[(1R,2R)-2-[[3,5-bis(trifluoromethyl)phenyl]sulfonylamino]cyclohexyl]-3-methylbutanamide
  参考文献：
  名称：

  Chiral amine organocatalysts for the syn-aldol reaction involving substituted benzaldehydes and hydroxyacetone

  摘要：

  A new series of cyclohexanediamine organocatalysts that contain the primary amine functionality has been designed, synthesized and tested as catalysts for the asymmetric aldol reaction involving hydroxyacetone and a variety of substituted benzaldehydes. High enantioselectivites and diasteroselectivites were obtained using catalyst la for these reactions. A key step in this reaction for the formation of the syn-product is the formation of a stable intramolecular hydrogen bonded Z-enamine isomer, which in addition to the steric bulk of the catalyst, serve to dictate the course of the stereochemical outcome of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.05.021
• 作为产物：
  描述：

  3,5-二三氟甲基苯磺酰氯 、 (1R,2R)-1,2-diaminocyclohexane 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 N-[(1R,2R)-2-氨基环己基]-3,5-双(三氟甲基)苯亚磺酰胺
  参考文献：
  名称：

  双官能单磺酰基DPEN盐催化的酮向马来酰亚胺的对映体选择性迈克尔加成反应。

  摘要：

  据报道，由简单的双官能伯胺单磺酰基DPEN盐催化的各种酮向马来酰亚胺的对映体选择性迈克尔加成反应是前所未有的，并以良好的对等收率（高达99％）和优异的对映选择性（高达99％）提供了所需的加合物。

  DOI：

  10.1039/c0cc00774a

文献信息

• A highly efficient asymmetric Michael addition of α,α-disubstituted aldehydes to maleimides catalyzed by primary amine thiourea salt
  作者：Feng Yu、Zhichao Jin、Huicai Huang、Tingting Ye、Xinmiao Liang、Jinxing Ye

  DOI：10.1039/c0ob00154f

  日期：——

  The first highly efficient Michael addition of challenging α,α-disubstituted aldehydes to maleimides catalyzed by a simple bifunctional primary amine thiourea catalyst/benzoic acid system has been successfully developed to generate quaternary carbon centers in high yields (up to 99%) with excellent enantioselectivities (91–99%).

  简单的双官能伯胺硫脲催化剂/催化的将高挑战性的α，α-二取代的醛首次高效加成到马来酰亚胺上/苯甲酸 系统已成功开发以生成四元数 碳 中心高收率（高达99％）和出色的对映选择性（91–99％）。
• Chiral Integrated Catalysts Composed of Bifunctional Thiourea and Arylboronic Acid: Asymmetric Aza-Michael Addition of α,β-Unsaturated Carboxylic Acids
  作者：Noboru Hayama、Takumi Azuma、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1248/cpb.c15-00983

  日期：——

  The first intermolecular asymmetric Michael addition of nitrogen-nucleophiles to alpha,beta-unsaturated carboxylic acids was achieved through a new type of arylboronic acid equipped with chiral aminothiourea. The use of BnONH2 as a nucleophile gives a range of enantioenriched beta-(benzyloxy)amino acid derivatives in good yields and with high enantioselectivity (up to 90% yield, 97% enantiomeric excess

  氮亲核试剂向α，β-不饱和羧酸的首次分子间不对称迈克尔加成反应是通过配备手性氨基硫脲的新型芳基硼酸实现的。使用BnONH2作为亲核试剂，可以以高收率和高对映选择性（高达90％的收率，97％的对映体过量（ee））获得​​一系列对映体富集的β-（苄氧基）氨基酸衍生物。将获得的产物有效地转化为旋光性β-氨基酸和1,2-二胺衍生物。
• Iridium/<i>f</i>-diaphos catalyzed asymmetric hydrogenation of 2-imidazolyl aryl/alkyl ketones
  作者：Ze Wang、Xianghua Zhao、Shiliang Wang、An Huang、Yifan Wang、Jiaying He、Fei Ling、Weihui Zhong

  DOI：10.1039/d1ob01860d

  日期：——

  The iridium/f-diaphos L1, L5 or L12 catalyzed asymmetric hydrogenation of 2-imidazolyl aryl/alkyl ketones to afford two enantiomers of the desired chiral alcohols with high conversions (up to 99% yield) and moderate to excellent enantioselectivities (61% - >99% ee) was realized for the first time. This protocol could be easily conducted on a gram-scale with a TON of 9700.

  铱/ f-二磷L1、L5或L12催化 2-咪唑基芳基/烷基酮的不对称氢化，得到所需手性醇的两种对映异构体，具有高转化率（高达 99% 的产率）和中等至优异的对映选择性（61% - >99% ee ) 首次实现。该协议可以在 TON 为 9700 的克级上轻松执行。
• Enantioselective Michael addition of ketones to maleimides catalyzed by bifunctional monosulfonyl DPEN salt
  作者：Feng Yu、Xiaomin Sun、Zhichao Jin、Shigang Wen、Xinmiao Liang、Jinxing Ye

  DOI：10.1039/c0cc00774a

  日期：——

  An unprecedented enantioselective Michael addition of various ketones to maleimides catalyzed by a simple bifunctional primary amine, monosulfonyl DPEN salt, is reported and provides the desired adducts in good to excellent yields (up to 99%) with excellent enantioselectivities (up to 99%).

  据报道，由简单的双官能伯胺单磺酰基DPEN盐催化的各种酮向马来酰亚胺的对映体选择性迈克尔加成反应是前所未有的，并以良好的对等收率（高达99％）和优异的对映选择性（高达99％）提供了所需的加合物。
• Chiral amine organocatalysts for the syn-aldol reaction involving substituted benzaldehydes and hydroxyacetone
  作者：Dhruba Sarkar、Kurt Harman、Subrata Ghosh、Allan D. Headley

  DOI：10.1016/j.tetasy.2011.05.021

  日期：2011.5

  A new series of cyclohexanediamine organocatalysts that contain the primary amine functionality has been designed, synthesized and tested as catalysts for the asymmetric aldol reaction involving hydroxyacetone and a variety of substituted benzaldehydes. High enantioselectivites and diasteroselectivites were obtained using catalyst la for these reactions. A key step in this reaction for the formation of the syn-product is the formation of a stable intramolecular hydrogen bonded Z-enamine isomer, which in addition to the steric bulk of the catalyst, serve to dictate the course of the stereochemical outcome of the reaction. (C) 2011 Elsevier Ltd. All rights reserved.