(6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydropyrrolo [1,2-c]oxazol-3(1H)-one | 1218989-18-4

• 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: (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydropyrrolo [1,2-c]oxazol-3(1H)-one
• 英文别名: (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydro-1H,3H-pyrrolo[1,2-c]oxazol-3-one；(6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one；(6R,7aS)-1,1-diphenyl-6-(prop-2-ynyloxy)tetrahydropyrrolo[1,2-c]oxazol-3(1H)-one
• CAS: 1218989-18-4
• 化学式: C₂₁H₁₉NO₃
• 分子量: 333.387
• InChiKey: SIJKOCZGWQABKP-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydropyrrolo [1,2-c]oxazol-3(1H)-one 在 三乙胺 、 potassium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 生成 (2S,4R)-2-(diphenyl((trimethylsilyl)oxy)methyl)-4-(prop-2-yn-1-yloxy)pyrrolidine
  参考文献：
  名称：

  Solid supported Hayashi–Jørgensen catalyst as an efficient and recyclable organocatalyst for asymmetric Michael addition reactions

  摘要：

  A comparison of three different catalytic systems for the efficient, asymmetric synthesis of N-({(3R,4R)-4-[(benzyloxy)methyllpyrrolidin-3-yl]methyl)-N-(2-methylpropyl)benzenesulfonamide 1 (BZN) is described. The presented strategy is based on the organocatalytic Michael addition of aldehyde 2 to trans-nitroalkene 3, and subsequent reductive cyclization. High yields, enantio-, and diastereoselectivities were achieved in the Michael addition by application of a POSS- or Wang resin-supported Hayashi-Jorgensen catalyst. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2017.10.016
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.16h， 生成 (6R,7aS)-1,1-diphenyl-6-(prop-2-yn-1-yloxy)tetrahydropyrrolo [1,2-c]oxazol-3(1H)-one
  参考文献：
  名称：

  有机催化对映选择性连续流环丙烷化

  摘要：

  已经制备了一组六种固体负载的二芳基脯氨醇催化剂（根据固定策略和聚合物载体的类型而异），并将其应用于对映选择性环丙烷化反应。选定的候选对象允许执行长流实验（48小时），并通过顺序流实验生成12个环丙烷的库。该方法的温和性和实用性使得能够进行伸缩过程，其中将流出物直接用于维蒂希（Wittig）流动反应中。

  DOI：

  10.1021/acs.orglett.6b03156

文献信息

• Efficient, Enantioselective Iminium Catalysis with an Immobilized, Recyclable Diarylprolinol Silyl Ether Catalyst
  作者：Ina Mager、Kirsten Zeitler

  DOI：10.1021/ol100166z

  日期：2010.4.2

  A highly efficient approach for the synthesis, application, and recycling of immobilized diarylprolinol silyl ethers was developed. The MeOPEG-supported Jørgensen−Hayashi catalyst provides unchanged reactivity and selectivity as compared to the homogeneous catalyst, as demonstrated for the Michael addition of nitromethane to α,β-unsaturated aldehydes via iminium activation. In addition, the immobilization

  开发了一种高效的固定化二芳基脯氨醇甲硅烷基醚的合成，应用和回收方法。与均相催化剂相比，MeOPEG负载的Jørgensen-Hayashi催化剂提供了不变的反应性和选择性，如通过亚胺基活化将硝基甲烷迈克尔加成到α，β-不饱和醛上所证明的。另外，固定化使得可以简单，无柱地分离纯净的，敏感的醛产物，因此对于在更复杂的合成中的应用可能是有用的。
• Development of novel triazole based dendrimer supported spiroborate chiral catalysts for the reduction of (<i>E</i>)-<i>O</i>-benzyl oxime: an enantioselective synthesis of (<i>S</i>)-dapoxetine
  作者：Ramasamy Anandhan、Mandapati Bhargava Reddy、Murugesan Sasikumar

  DOI：10.1039/c9nj03217g

  日期：——

  Novel dendrimer supported spiroborate catalysts 2 and 3 have been synthesized using a click reaction as a key step. The catalytic efficiency of the catalysts have been verified with reduction of (E)-O-benzyl oxime 13 as a model substrate. Catalyst 3 was found to be better than catalyst 2 as the chemical yield and enantiomeric excess were significantly high with the former catalyst. Thus, catalyst 3 has

  使用点击反应作为关键步骤，合成了新型的由树状聚合物负载的螺硼酸酯催化剂2和3。已经通过还原（E）-O-苄基肟13作为模型底物证实了催化剂的催化效率。发现催化剂3比催化剂2更好，因为前一种催化剂的化学产率和对映体过量显着高。因此，催化剂3已成功用于有效合成（S）-多巴西汀14三个步骤可实现94％的ee和46％的总产率。这些催化剂可以很容易地通过溶剂沉淀技术从反应溶液中回收，并且可以重复使用五次而不会显着降低活性和对映选择性。
• Enantioselective Heterogeneous Synergistic Catalysis for Asymmetric Cascade Transformations
  作者：Luca Deiana、Lorenza Ghisu、Samson Afewerki、Oscar Verho、Eric V. Johnston、Niklas Hedin、Zoltan Bacsik、Armando Córdova

  DOI：10.1002/adsc.201400291

  日期：2014.8.11

  AbstractA modular design for a novel heterogeneous synergistic catalytic system, which simultaneously activates the electrophile and nucleophile by the combined activation modes of a separate metal and non‐metal catalyst, for asymmetric cascade transformations on a solid surface is disclosed. This modular catalysis strategy generates carbocycles (up to 97.5:2.5 er) as well as spirocyclic oxindoles (97.5:2.5 to >99:0.5 er), containing all‐carbon quaternary centers, in a highly enantioselective fashion via a one‐pot dynamic relay process.magnified image