(S)-N-(1-(diphenylphosphanyl)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide | 1239020-07-5

• 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: (S)-N-(1-(diphenylphosphanyl)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide
• 英文别名: (S)-N-(1-(diphenylphosphino)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide；N-[(2S)-1-diphenylphosphanyl-3,3-dimethylbutan-2-yl]-3,5-bis(trifluoromethyl)benzamide
• CAS: 1239020-07-5
• 化学式: C₂₇H₂₆F₆NOP
• 分子量: 525.474
• InChiKey: NNEYFISCDMOQKY-HSZRJFAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  36
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-(diphenylphosphanyl)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide 、 3,5-双三氟甲基苄基溴 以 甲苯 为溶剂， 反应 8.0h， 以94%的产率得到(S)-(2-(3,5-bis(trifluoromethyl)benzamido)-3,3-dimethylbutyl)(3,5-bis(trifluoromethyl)benzyl)diphenylphosphonium bromide
  参考文献：
  名称：

  Enantioselective desymmetrization of meso-aziridines with aromatic thiols catalyzed by chiral bifunctional quaternary phosphonium salts derived from α-amino acids

  摘要：

  Desymmetrization of meso-aziridines with aromatic thiols was realized by using alpha-amino acids-derived chiral quaternary phosphonium salts catalysts to provide chiral beta-amino sulfides with high yields (up to 99%) and in moderate enantioselectivities (up to 70%). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.001
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲酸 、 (S)-1-(二苯基膦基)-2-氨基-3-二甲基丁烷 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以63%的产率得到(S)-N-(1-(diphenylphosphanyl)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  简单双功能N-酰基氨基膦酸酯催化的脲基酸酯和双活化烯烃的不对称[3 + 2]环加成反应

  摘要：

  双官能催化剂：开发了简单的双官能N酰基氨基膦（如1）来催化脲基酸酯和双活化烯烃之间的首次不对称[3 + 2]环加成反应。环加成反应提供多功能的手性环戊烯，具有独特的区域选择性，并具有良好的对映选择性和良好的收率。

  DOI：

  10.1002/anie.201000446
• 作为试剂：
  描述：

  苯甲酰甲酸乙酯 、 在 (S)-N-(1-(diphenylphosphanyl)-3,3-dimethylbutan-2-yl)-3,5-bis(trifluoromethyl)benzamide 作用下， 以 甲苯 为溶剂， 以75%的产率得到(E)-ethyl 5-(3-cyano-1-ethoxy-1-oxopropan-2-ylidene)-2-phenyltetrahydrofuran-2-carboxylate
  参考文献：
  名称：

  Phosphine Catalyst-Controlled Cycloaddition or Dienylation Reactions of Trifluoromethyl Aryl Ketones with Bis-Substituted Allenoates

  摘要：

  A chemoselective phosphine-catalyzed cyclo-addition or dienylation reaction between trifluoromethyl-substituted ketones and bis-substituted allenoates was described. Under the catalysis of triarylphosphine, the reaction gave a range of trifluoromethylated tetrahydrofurans with broad substrate tolerance and good to excellent stereo-selectivity, while the use of trialkylphosphine switched the reaction pathway to furnish CF3-substituted dienyl tertiary alcohols, chemoselectivey. Moreover, a preliminary study on the asymmetric version of the reaction was also performed, which represents the first example of a phosphine-catalyzed asymmetric reaction between allenoates and carbonyl compounds.

  DOI：

  10.1021/jo401462c

文献信息

• Enantioselective γ-Addition-Driven Cascade of β,γ-Unsaturated Ketones by Ion-Pair Catalysis: Access to Chiral 1,3-Dioxolochroman Scaffolds
  作者：Xuemei Wang、Liang Zhou、Hongkui Zhang、Xiaoyu Ren、Guowei Gao、Tianli Wang

  DOI：10.1021/acs.orglett.1c03567

  日期：2022.1.14

  A highly enantioselective γ-addition-driven cascade of β,γ-unsaturated carbonyl compounds by bifunctional ion-pair catalysis has been developed. With this protocol, a range of functionalized chiral 1,3-dioxolochroman derivatives were prepared in high yields with superior stereoselectivities (>99% ee and >20:1 dr). The utility of this method was demonstrated by one-pot synthesis, scaled-up preparation

  已经通过双功能离子对催化开发了一种高度对映选择性的 γ-加成驱动的 β,γ-不饱和羰基化合物级联反应。使用该协议，一系列功能化的手性 1,3-二氧杂色满衍生物以高产率制备，具有出色的立体选择性（>99% ee和 >20:1 dr）。该方法的实用性通过一锅合成、放大制备和简便转化得到证明。此外，机理研究提供了对反应途径和手性诱导起源的见解。
• Highly Enantioselective Synthesis of Phosphorus‐Containing ϵ‐Benzosultams by Bifunctional Phosphonium Salt‐Promoted Hydrophosphonylation
  作者：Song Zhang、Zhenghuai Feng、Chunhui Jiang、Xiaojun Yu、Jianke Pan、Juan Du、Zhiyu Jiang、Yuan Chen、Tianli Wang

  DOI：10.1002/chem.202101038

  日期：2021.8.5

  with diverse biological activities. A series of chiral ϵ-benzosultams bearing phosphorus functionalities was synthesized by catalytic asymmetric hydrophosphonylation in the presence of a bifunctional phosphonium salt catalyst. The desired hydrophosphonylation products were obtained in good yields with high enantioselectivities, and scale-up reactions and further derivations were successfully accomplished

  ϵ-Benzosultam 衍生物是具有多种生物活性的潜在候选药物。在双功能鏻盐催化剂存在下，通过催化不对称氢膦酰化反应合成了一系列带有磷官能团的手性 ϵ-benzosultams。以良好的收率和高对映选择性获得了所需的氢膦酰化产物，并且成功地完成了放大反应和进一步的衍生。还进行了一些对照实验以阐明这种化学转化的合理反应机制。
• Thiourea–Quaternary Ammonium Salt Catalyzed Asymmetric 1, 3-Dipolar Cycloaddition of Imino Esters To Construct Spiro[pyrrolidin-3,3′-oxindoles]
  作者：Jia-Xing Zhang、Hong-Yu Wang、Qiao-Wen Jin、Chang-Wu Zheng、Gang Zhao、Yong-Jia Shang

  DOI：10.1021/acs.orglett.6b02098

  日期：2016.10.7

  A highly enantioselective 1,3-dipolar cycloaddition of imino esters with methyleneindolinones has been realized by using readily available thiourea–quaternary ammonium salts as phase-transfer catalysts, enabling efficient construction of a range of chiral spiro[pyrrolidin-3,3′-oxindoles] in good yields with excellent enantioselectivities under mild conditions.

  通过使用容易获得的硫脲-季铵盐作为相转移催化剂，实现了亚氨基吲哚酮与亚氨基吲哚酮类化合物的高度对映选择性1,3-偶极环加成反应，从而能够高效构建一系列手性螺[吡咯烷酮-3,3'-羟吲哚在温和条件下具有良好的对映选择性和良好的收率。