(S)-3-cinnamoyl-4-isopropyloxazolidin-2-one | 454692-66-1

• 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: (S)-3-cinnamoyl-4-isopropyloxazolidin-2-one
• 英文别名: (S)-3-cinnamoyl-4-isopropyl-2-oxazolidinone；(4S)-3-(3-phenylprop-2-enoyl)-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS: 454692-66-1
• 化学式: C₁₅H₁₇NO₃
• 分子量: 259.305
• InChiKey: PNZYNDNOSVFRMU-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-3-cinnamoyl-4-isopropyloxazolidin-2-one 在 [Cu(2,9-bis(4-methoxyphenyl)-1,10-phenanthroline)₂]Cl 、 溴 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 15.0h， 生成 (R)-3-((R)-2-((S)-methoxy(phenyl)methyl)pent-4-enoyl)-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  [Cu（dap）2Cl]在碳-碳键形成反应中作为高效可见光驱动的光氧化还原催化剂

  摘要：

  铜日渐成熟：[Cu（dap）2 Cl]被证明是用于原子转移自由基加成反应以及烯丙基化反应（参见方案）的出色光氧化还原催化剂，为常用的铱提供了有吸引力的替代方法。和钌基催化剂。

  DOI：

  10.1002/chem.201200967
• 作为产物：
  描述：

  (S)-3-((2S,3R)-2,3-dibromo-3-phenylpropanoyl)-4-isopropyloxazolidin-2-one 在 tris(2,2'-bipyridyl)ruthenium dichloride 、 1,5-二甲氧基萘 、 维生素 C 作用下， 以 甲醇 、 水 为溶剂， 反应 5.0h， 以89%的产率得到(S)-3-cinnamoyl-4-isopropyloxazolidin-2-one
  参考文献：
  名称：

  可见光光氧化还原催化：邻二溴，α-卤代和α，α-二溴羰基化合物的脱卤作用

  摘要：

  使用催化三氯化三（2,2'-联吡啶基）钌（Ru（bpy）3 Cl 2）与1,5-结合可以有效地使vic -Dibromo-，α-卤代或α，α-二溴代羰基化合物脱卤二甲氧基萘（DMN）和抗坏血酸盐作为牺牲电子给体。对于该方法，提出了可见光促进的光催化循环，该循环涉及通过自由基中间体还原碳卤键。

  DOI：

  10.1021/jo102239x

文献信息

• Diastereoselective copper-catalysed 1,4-addition of Grignard reagents to N-enoyl oxazolidinones
  作者：Michal Drusan、Zuzana Galeštoková、Radovan Šebesta

  DOI：10.1039/c3ra42024h

  日期：——

  Conjugate additions of organometallic reagents to α,β-unsaturated carboxylic acid derivatives give access to numerous β-substituted chiral building blocks. Chiral oxazolidinones serve as useful surrogates of carboxylic function in the asymmetric conjugate addition of Grignard reagents. N-Enoyl oxazolidinones undergo this 1,4-addition with a catalytic amount of copper salt and using either chiral or

  将有机金属试剂共轭添加到α，β-不饱和羧酸衍生物中可以得到许多β-取代的手性结构单元。手性恶唑烷酮在格氏试剂的不对称共轭加成中可用作有用的羧基官能替代物。N-烯丙基恶唑烷酮与1,4-催化量的铜盐进行加成反应，并使用手性或非手性膦配体。特别地，手性二茂铁基膦烷恶唑啉被证明可用于实现高非对映选择性。以高收率和高非对映选择性（直至单一非对映异构体）获得所得的N-酰基恶唑烷酮。
• Stereoselective [2 + 2] photodimerization: a viable strategy for the synthesis of enantiopure cyclobutane derivatives
  作者：Fabrizio Medici、Alessandra Puglisi、Sergio Rossi、Laura Raimondi、Maurizio Benaglia

  DOI：10.1039/d3ob00232b

  日期：——

  The [2 + 2] photodimerization of cinnamic acid derivatives to afford enantiopure cyclobutanes has been investigated. The use of a chiral auxiliary represents a convenient and straightforward method to exert enantiocontrol on the reaction. By exploiting Evans oxazolidinones, the stereoselective light-driven cyclisation affords a functionalised cyclobutane ring with up to 99% enantiocontrol after removing

  已经研究了肉桂酸衍生物的 [2 + 2] 光二聚化以提供对映体纯环丁烷。使用手性助剂代表了一种对反应进行对映控制的方便且直接的方法。通过利用 Evans 恶唑烷酮，立体选择性光驱动环化提供了功能化的环丁烷环，在去除手性助剂后具有高达 99% 的对映体控制。流入实验使我们能够进一步提高方法的效率，从而实现高转化率和出色的对映选择性。
• An Access to Chiral Phthalides: Enantioselective Synthesis of Escitalopram
  作者：Rosaria Schettini、Antonella Dentoni Litta、Arianna Sinibaldi、Assunta D'Amato、Alicja M. Araszczuk、Marina Sicignano、Letizia Pagliarulo、Simone Naddeo、Giovanni Pierri、Francesco De Riccardis、Irene Izzo、Giorgio Della Sala

  DOI：10.1002/adsc.202400007

  日期：2024.4.9

  A method for the asymmetric synthesis of phthalides containing a stereogenic γ-carbon has been described. The protocol, based on the arylogous Michael addition to chiral alkenoyl oxazolidinones catalyzed by a crown ether under phase-transfer conditions does not require anhydrous conditions and uses commercially available materials. A complete syn-stereocontrol is achieved and facial diastereoselectivities

  描述了一种不对称合成含有立构γ-碳的苯并呋喃酮的方法。该方案基于在相转移条件下由冠醚催化的手性烯酰基恶唑烷酮的芳源迈克尔加成，不需要无水条件并使用市售材料。实现了完整的同步立体控制，并且面部非对映选择性为中等至优秀（62:38 至 99:1 dr）。通过色谱法纯化主要非对映异构体并选择性裂解手性助剂，得到对映体纯迈克尔产物。该方案已应用于艾司西酞普兰的正式合成。
• Diastereoselective Synthesis of Tetrahydrofurans by Lewis Acid Catalyzed Intermolecular Carbenoid–Carbonyl Reaction–Cycloaddition Sequences: Unusual Diastereoselectivity of Lewis Acid Catalyzed Cycloadditions
  作者：Yuta Hashimoto、Kennosuke Itoh、Akikazu Kakehi、Motoo Shiro、Hiroyuki Suga

  DOI：10.1021/jo400858u

  日期：2013.6.21

  The effects of including metal salts for three. component reactions involving alpha-alkyl-alpha-diazo esters, aromatic aldehydes, and 3-(2-alkenoyl)-2-oxazolidinones are described, in terms of yields and diastereoselectivities. Metal tetrafluorborates (10-30 mol %) such as Co(BF4)(2)center dot 6H(2)O, Ni(BF4)(2)center dot 6H(2)O, and AgBF4 were effective in delivering high yields and diastereoselectivities (93:7 to 99:1) of the corresponding tetrahydrofuran derivatives while suppressing the competitive formation of 1,3-dioxolane. Using (S)-3-(2-alkenoyl)-4-isopropyl-2-oxazolidinones as the dipolarophiles in the three-component reactions, in the presence of Ni(BF4)(2)center dot 6H(2)O or Co(ClO4)(2)center dot 6H(2)O (10-30 mol %), optically active tetrahydrofurans that possess four successive asymmetric centers were synthesized in high diastereoselectivities (99:1). On the basis of the configuration of the cycloadduct using the X-ray analysis, the high diastereoselectivity could be explained by the unusual Re-face approach to the dipolarophile in the presence of the Lewis acid, proceeding through the s-cis conformer of the 3-(2-alkenoyl)-2-oxazolidinone with the two carbonyls in opposing directions (dipole-dipole interaction).
• Electroreductive 4-Pyridylation of Electron-deficient Alkenes with Assistance of Ni(acac)₂
  作者：Sheng Zhang、Lijun Li、Xinru Li、Junqi Zhang、Kun Xu、Guigen Li、Michael Findlater

  DOI：10.1021/acs.orglett.0c01014

  日期：2020.5.1

  An electroreductive 4-pyridylation of activated alkenes was developed in an undivided cell with the assistance of Ni(acac)(2) (acac = acetylacetone). This novel protocol is compatible with a broad range of electron-poor alkenes, which are commonly regarded as challenging substrates in the previous conventional approaches. Moreover, a series of cyclic voltammetric experiments were conducted to reveal the unique role of Ni(acac)(2) differentiating reduction process of reaction partners.