ethyl trans-2-[4-(tert-butyl)phenyl]cyclopropane-1-carboxylate | 115199-51-4

• 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: ethyl trans-2-[4-(tert-butyl)phenyl]cyclopropane-1-carboxylate
• 英文别名: (R)-ethyl 2-(4-(tert-butyl)phenyl)cyclopropanecarboxylate；ethyl (1R,2R)-2-(4-(tert-butyl)phenyl)cyclopropane-1-carboxylate；(1R,2R)-2-(4-tert-butylphenyl)cyclopropane-1-carboxylic acid ethyl ester；rel-Ethyl (1R,2R)-2-[4-(1,1-dimethylethyl)phenyl]cyclopropanecarboxylate；ethyl (1R,2R)-2-(4-tert-butylphenyl)cyclopropane-1-carboxylate
• CAS: 115199-51-4
• 化学式: C₁₆H₂₂O₂
• 分子量: 246.349
• InChiKey: UCDAWOWWZUSWFQ-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-叔丁基苄溴 、 alkaline earth salt of/the/ methylsulfuric acid 在 silver tetrafluoroborate 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 生成 ethyl trans-2-[4-(tert-butyl)phenyl]cyclopropane-1-carboxylate
  参考文献：
  名称：

  Two-Step Synthesis oftrans-2-Arylcyclopropane Carboxylates with 98-100 %ee by the Use of a Phosphazene Base

  摘要：

  Only the axial diastereomer of sulfonium salts 2 are formed upon alkylation of 1. Deprotonation of 2 results in ylides, which allow the highly enantioselective cyclopropanation of Michael systems. The chiral auxiliary 1 is recovered and can be reused.

  DOI：

  10.1002/(sici)1521-3773(19980703)37:12<1689::aid-anie1689>3.0.co;2-9

文献信息

• A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase
  作者：Richard Stenner、Jack W. Steventon、Annela Seddon、J. L. Ross Anderson

  DOI：10.1073/pnas.1915054117

  日期：2020.1.21

  activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.

  通过构建体内组装的、催化能力强的过氧化物酶 C45，我们最近证明了简单的、从头设计的血红素蛋白的催化潜力。在这里，我们展示了 C45 的酶活性延伸到卡宾到烯烃、杂环、醛和胺的高效和立体选择性分子间转移。这不仅是关于完全从头蛋白质中卡宾转移酶活性的报告，而且是通过任何酶的卡宾转移酶催化芳族杂环扩环的报告。
• Asymmetric Cyclopropanation of Styrenes Catalyzed by Metal Complexes of <i>D</i>₂-Symmetrical Chiral Porphyrin:  Superiority of Cobalt over Iron
  作者：Ying Chen、X. Peter Zhang

  DOI：10.1021/jo070997p

  日期：2007.7.1

  The cobalt(II) complex of D2-symmetric chiral porphyrin [Co(1)] is an effective catalyst for highly diastereoselective and enantioselective cyclopropanation of a broad range of styrene derivatives under mild conditions. Dimerization of diazo compounds, a common side reaction in metal-mediated carbene transfer processes, is minimized in a cobalt porphyrin-based system, obviating the need to employ excess

  D 2对称手性卟啉[Co（1）]的钴（II）配合物是在温和条件下对多种苯乙烯衍生物进行高度非对映选择性和对映选择性环丙烷化的有效催化剂。在基于钴卟啉的体系中，重氮化合物的二聚反应（在金属介导的卡宾转移过程中常见的副反应）被最小化，从而避免了使用过量底物和缓慢添加重氮化合物的需求。[Co（1）]的高催化活性和选择性显然是由于钴离子和手性卟啉1的适当组合，因为使用了具有相同配体[Fe（1）的铁（III）配合物）Cl]以低收率和差的对映选择性提供所需的环丙烷产物。
• Aqueous asymmetric cyclopropanation reactions in polymersome membranes
  作者：Matthijs C. M. van Oers、Loai K. E. A. Abdelmohsen、Floris P. J. T. Rutjes、Jan C. M. van Hest

  DOI：10.1039/c3cc48865a

  日期：——

  Copper-bis(oxazoline) functionalised polymersomes have been developed for asymmetric cyclopropanation reactions in water.

  氧杂环己烷基铜聚合物体在水中用于不对称环丙烷化反应。
• Z‐bpy, a New <i>C</i> ₂ ‐Symmetric Bipyridine Ligand and Its Application in Enantioselective Copper(I)‐Catalyzed Cyclopropanation of Olefins
  作者：Yizhao Ouyang、Miao Zhan、Jing Zhou、Jiao Jiao、Hao Hu、Yoichi M. A. Yamada、Pengfei Li

  DOI：10.1002/cjoc.201900141

  日期：2019.8

  A rigid C2‐symmetric chiral bipyridine ligand Z‐bpy with a triptycene‐like backbone was designed and synthesized from simple chemicals in a scalable route. Using this new ligand, copper(I) catalyzed cyclopropanation of styrenes with commercial ethyl diazoacetate produced various corresponding cyclopropanes in high yields, diastereoselectivity and enantioselectivity up to 97% ee.

  设计了刚性的C 2对称手性联吡啶配体Z-bpy，具有三萜类骨架，并通过简单的化学方法以可扩展的方式合成。使用这种新的配体，铜（I）与市售重氮乙酸乙酯催化苯乙烯的环丙烷化反应可高产率，非对映选择性和对映选择性高达97％ee生成各种相应的环丙烷。
• Axial Ligand Effects: Utilization of Chiral Sulfoxide Additives for the Induction of Asymmetry in (Salen)ruthenium(ii) Olefin Cyclopropanation Catalysts
  作者：Jason A. Miller、Bradley A. Gross、Michael A. Zhuravel、Wiechang Jin、SonBinh T. Nguyen

  DOI：10.1002/anie.200460887

  日期：2005.6.20