(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea | 1223441-20-0

• 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)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea
• 英文别名: (S)-1-(3,5-Bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphanyl)-3-phenylpropan-2-yl)thiourea；1-[3,5-bis(trifluoromethyl)phenyl]-3-[(2S)-1-diphenylphosphanyl-3-phenylpropan-2-yl]thiourea
• CAS: 1223441-20-0
• 化学式: C₃₀H₂₅F₆N₂PS
• 分子量: 590.572
• InChiKey: QTTGLTFITODMFT-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea 在 吡啶硼烷 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of new mono and bis amides projected as potential histone deacetylase (HDAC) inhibitors

  摘要：

  In our ongoing efforts to discover new potent histone deacetylase (HDAC) inhibitors as promising anticancer candidates, we designed and synthesized a small collection of 3-substituted amines possessing macro heterocyclic skeletons bearing variable-length tails. As a metal binder domain, all the compounds possess an amide function suitable for Zn2+ chelation in the enzyme active site. A combination of solution and solid phase techniques were employed to synthesize the compounds and, as the key synthetic step to obtain the rings, a ring closing metathesis (RCM) reaction was adopted. The putative affinity of the compounds for the histone deacetylase-like protein (HDLP) model receptor active site was explored through docking calculations, and we also report preliminary studies on their pharmacological proper-ties. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.01.061
• 作为产物：
  描述：

  3,5-双(三氟甲基)苯基异硫氰酯 、 [(ΑS)-Α-[(二苯基膦)甲基]苯乙胺] 以 二氯甲烷 为溶剂， 以75%的产率得到(S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea
  参考文献：
  名称：

  氨基酸衍生的硫代硫脲催化的对映选择性分子内Morita-Baylis-Hillman反应

  摘要：

  已经开发了一系列衍生自l-氨基酸的手性双功能膦硫脲，以促进对映选择性分子内Morita-Baylis-Hillman反应。该方法在温和条件下提供了高达84％ee的环状羟基烯酮和良好的收率。

  DOI：

  10.1016/j.tet.2010.01.085
• 作为试剂：
  描述：

  5,6-二氟靛红 在 哌啶 、 (S)-1-(3,5-bis(trifluoromethyl)phenyl)-3-(1-(diphenylphosphino)-3-phenylpropan-2-yl)thiourea 、 caesium carbonate 、 potassium iodide 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， 反应 34.25h， 生成 (R)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)-5,6-difluoro-1-methyl-3-(3-oxobut-1-en-2-yl)indolin-2-one
  参考文献：
  名称：

  非对称分子间Rauhut-Curer反应，用于构建具有季位立体中心的3,3-二取代的吲哚

  摘要：

  实现了利用乙烯基酮和衍生自靛红的对苯二甲酰甲烷进行的远程Rauhut-Currier交叉反应，该反应已成功使用双官能膦催化，以优异的对映选择性和高收率提供了手性3,3-二取代的羟吲哚。机理研究证明了乙烯基酮的烷基氢的关键作用，可以想象它通过氢键与对苯二甲酰甲基羰基通过氢键相互作用，为新型不对称反应的设计提供了新的见识。

  DOI：

  10.1002/adsc.201700649

文献信息

• Asymmetric Strecker Reactions Catalyzed by Thiourea Phosphonium and Ammonium Salts
  作者：Hongyu Wang、Kaiye Wang、Yanfei Ren、Na Li、Bo Tang、Gang Zhao

  DOI：10.1002/adsc.201700029

  日期：2017.6.6

  The application of asymmetric phase‐transfer catalysis to the Strecker reaction of ketimines was realized utilizing bifunctional thiourea‐phosphonium salts. The asymmetric Strecker reaction of aldimines was also realized utilizing quaternary ammonium salts derived from amino acids.

  利用双功能硫脲-phosph盐实现了不对称相转移催化在酮亚胺的Strecker反应中的应用。还利用衍生自氨基酸的季铵盐实现了亚胺的不对称Strecker反应。
• Thiourea-phosphonium salts from amino acids: cooperative phase-transfer catalysts in the enantioselective aza-Henry reaction
  作者：Dongdong Cao、Zhuo Chai、Jiaxing Zhang、Zhengqing Ye、Hua Xiao、Hongyu Wang、Jinhao Chen、Xiaoyu Wu、Gang Zhao

  DOI：10.1039/c3cc42864h

  日期：——

  New chiral bifunctional thiourea-phosphonium salts have been developed based on natural amino acids as highly efficient phase-transfer catalysts in the enantioselective aza-Henry reaction.

  已经基于天然氨基酸开发了新的手性双官能硫脲-phosph盐，作为对映选择性氮杂-亨利反应中的高效相转移催化剂。
• Synthesis of new mono and bis amides projected as potential histone deacetylase (HDAC) inhibitors
  作者：Stefania Terracciano、Maria Giovanna Chini、Giuseppe Bifulco、Elisabetta D'Amico、Stefania Marzocco、Raffaele Riccio、Ines Bruno

  DOI：10.1016/j.tet.2010.01.061

  日期：2010.3

  In our ongoing efforts to discover new potent histone deacetylase (HDAC) inhibitors as promising anticancer candidates, we designed and synthesized a small collection of 3-substituted amines possessing macro heterocyclic skeletons bearing variable-length tails. As a metal binder domain, all the compounds possess an amide function suitable for Zn2+ chelation in the enzyme active site. A combination of solution and solid phase techniques were employed to synthesize the compounds and, as the key synthetic step to obtain the rings, a ring closing metathesis (RCM) reaction was adopted. The putative affinity of the compounds for the histone deacetylase-like protein (HDLP) model receptor active site was explored through docking calculations, and we also report preliminary studies on their pharmacological proper-ties. (C) 2010 Elsevier Ltd. All rights reserved.
• The enantioselective intramolecular Morita–Baylis–Hillman reaction catalyzed by amino acid-derived phosphinothiourea
  作者：Jing-Jing Gong、Kui Yuan、Hong-Liang Song、Xin-Yan Wu

  DOI：10.1016/j.tet.2010.01.085

  日期：2010.3

  A series of chiral bifunctional phosphinothioureas derived from l-amino acids have been developed to promote the enantioselective intramolecular Morita–Baylis–Hillman reaction. The process afforded the cyclic hydroxyl enones with up to 84% ee and good yields under mild conditions.

  已经开发了一系列衍生自l-氨基酸的手性双功能膦硫脲，以促进对映选择性分子内Morita-Baylis-Hillman反应。该方法在温和条件下提供了高达84％ee的环状羟基烯酮和良好的收率。