(4S)-4-phenyl-3-((2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl)-1,3-oxazolidine-2-one | 741280-87-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (4S)-4-phenyl-3-((2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl)-1,3-oxazolidine-2-one
• 英文别名: (4S)-3-[3-[3-(Trifluoromethyl)phenyl]acryloyl]-4beta-phenyloxazolidine-2-one；(4S)-4-phenyl-3-[(E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl]-1,3-oxazolidin-2-one
• CAS: 741280-87-5
• 化学式: C₁₉H₁₄F₃NO₃
• 分子量: 361.32
• InChiKey: NVXOGOGVJGTELY-ZNFPLGDCSA-N

物化性质

• 沸点：
  449.4±55.0 °C(Predicted)
• 密度：
  1.362±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  二氯胺T 、 (4S)-4-phenyl-3-((2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl)-1,3-oxazolidine-2-one 在 4 A molecular sieve 、 三氟甲烷磺酸亚铜(I)苯联合体 (2:1) 、 1-butyl-3-methylimidazolium Tetrafluoroborate 作用下， 反应 12.0h， 生成 N-[(S)-1-[(R)-Chloro-(3-trifluoromethyl-phenyl)-methyl]-2-oxo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-ethyl]-4-methyl-benzenesulfonamide 、 N-[(R)-1-[(S)-Chloro-(3-trifluoromethyl-phenyl)-methyl]-2-oxo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-ethyl]-4-methyl-benzenesulfonamide
  参考文献：
  名称：

  Ionic Liquid Media Resulted in the First Asymmetric Aminohalogenation Reaction of Alkenes

  摘要：

  [Graphics]The first asymmetric aminohalogenation of functionalized alkenes has been established. The ionic liquid [bmim][BF4] was found to be the only effective media for success as normal organic solvents failed to give any product for this reaction. The reaction is also very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide, and catalyst, together with 4 A molecular sieves at room temperature in [bmim][BF4] in any convenient vial of appropriate size without special protection from inert gases. Good chemical yields (60-72%) and diastereoselectivities (up to 75% de) have been obtained with a good scope of substrates. The resulting individual diastereomers have been cleanly separated via column chromatography. The absolute stereochemistry of the reaction was unambiguously determined by X-ray structural analysis.

  DOI：

  10.1021/ol048045i
• 作为产物：
  描述：

  3-(E)-(三氟甲基)肉桂酸 、 (S)-4-苯基-2-恶唑烷酮 生成 (4S)-4-phenyl-3-((2E)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl)-1,3-oxazolidine-2-one
  参考文献：
  名称：

  几乎完全控制亲核甘氨酸与（S）-或（R）-3-（E-烯丙基）-4-苯基-1,3-恶唑烷-2-的非手性当量之间的迈克尔加成反应中的简单和非对映选择性一：制备β-取代的焦谷氨酸和脯氨酸的实用方法

  摘要：

  这项研究表明，用于控制亲核甘氨酸等价物和α，β -不饱和羧酸衍生物之间的迈克尔加成反应的立体化学结果的新策略：非手性的Ni之间的加成反应（II）甘氨酸的席夫碱用的复形ö - [ N -α-羟甲基氨基]苯乙酮和（S）-或（R）-3-（E（-烯酰基）-4-苯基-1,3-恶唑烷-2-酮在室温下在非螯合有机碱存在下发生，最显着的是，在两个新形成的立体异构中心均具有很高的立体选择性。因此，发现手性的4-苯基-1，3-恶唑烷-2-酮部分可有效地控制甘氨酸衍生的烯酸酯的非对映选择性和迈克尔受体的C，C双键。在这项工作中开发的新策略在方法论上优于以前的方法，最显着的是在通用性和综合效率方面。优异的化学收率和非对映选择性，再加上简单的实验步骤，使得本发明的方法可立即用于制备各种3取代的焦谷氨酸和相关氨基酸（谷氨酸，谷氨酰胺，脯氨酸等）。

  DOI：

  10.1021/jo0495438

文献信息

• Pyrrolidine derivative or salt thereof
  申请人：Hachiya Shunichiro

  公开号：US20090062366A1

  公开（公告）日：2009-03-05

  [Problem] To provide a compound which may be used in treating diseases in which a calcium sensing receptor (CaSR) is concerned, particularly hyperparathyroidism. [Means for Resolution] It was found that novel pyrrolidine derivatives which are characterized by the possession of aminomethyl group substituted with arylalkyl group or the like, or salts thereof, have excellent CaSR agonistic regulatory activity and also have excellent selectivity with CYP2D6 inhibitory activity having a possibility of causing drug interaction. Based on the above, these novel pyrrolidine derivatives are useful as therapeutic agents for treating diseases in which CaSR is concerned (hyperparathyroidism, renal osteodystrophy, hypercalcemia and the like).

  [问题] 提供一种可用于治疗钙敏感受体（CaSR）相关疾病，特别是甲状旁腺功能亢进症的化合物。 [解决方法] 发现了一种新型吡咯烷衍生物，其特征在于具有氨甲基基团，该基团被芳基烷基或类似物取代，或其盐，具有出色的CaSR激动调节活性，并且具有出色的选择性与CYP2D6抑制活性，可能导致药物相互作用。基于以上发现，这些新型吡咯烷衍生物可用作治疗CaSR相关疾病（甲状旁腺功能亢进症，肾性骨营养不良，高钙血症等）的治疗剂。
• PYRROLIDINE DERIVATIVE OR SALT THEREOF
  申请人：Astellas Pharma Inc.

  公开号：EP1882684A1

  公开（公告）日：2008-01-30

  [Problem] To provide a compound which may be used in treating diseases in which a calcium sensing receptor (CaSR) is concerned, particularly hyperparathyroidism. [Means for Resolution] It was found that novel pyrrolidine derivatives which are characterized by the possession of aminomethyl group substituted with arylalkyl group or the like, or salts thereof, have excellent CaSR agonistic regulatory activity and also have excellent selectivity with CYP2D6 inhibitory activity having a possibility of causing drug interaction. Based on the above, these novel pyrrolidine derivatives are useful as therapeutic agents for treating diseases in which CaSR is concerned (hyperparathyroidism, renal osteodystrophy, hypercalcemia and the like).

  [问题]提供一种可用于治疗钙传感受体（CaSR）相关疾病，特别是甲状旁腺机能亢进症的化合物。 [解决方法] 研究发现，新型吡咯烷衍生物（其特征在于具有被芳基烷基或类似基团取代的氨甲基）或其盐具有优异的 CaSR 激动调节活性，同时还具有优异的选择性和 CYP2D6 抑制活性，但有可能引起药物相互作用。基于以上所述，这些新型吡咯烷衍生物可作为治疗剂用于治疗与 CaSR 有关的疾病（甲状旁腺机能亢进症、肾性骨营养不良症、高钙血症等）。
• Chelation-controlled asymmetric aminohalogenation reaction
  作者：Yi-Ning Wang、Adiseshu Kattuboina、Teng Ai、Diya Banerjee、Guigen Li

  DOI：10.1016/j.tetlet.2007.08.099

  日期：2007.10

  The chelation-controlled asymmetric aminohalogenation of alpha,beta-unsaturated 3-aryl-N-acyl-N-4-phenyl-2-oxazolidinones have been established by using palladium(II) acetate as the catalyst and as the chelation metal. The reaction is very convenient to perform by simply mixing the three reactants, cinnamates, N,N-dichloro-p-toluenesulfonamide and catalyst together with 4 A molecular sieves at rt in any convenient vial of appropriate size without special protection from inert gases. Unlike the previous asymmetric aminohalogenation, the ionic liquid, [BMINl][NTf2], was found to be superior to [BMIM][BF4] as the reaction media. It was also found that palladium(II) acetate has to be used together with 1 equiv of MeCN to achieve the opposite chelation control. The resulting absolute stereochemistry of the product was unambiguously determined by X-ray structural analysis. (C) 2007 Elsevier Ltd. All rights reserved.
• US7585886B2
  申请人：——

  公开号：US7585886B2

  公开（公告）日：2009-09-08