methyl 1,2-diphenylcyclopropanecarboxylate | 42333-04-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: methyl 1,2-diphenylcyclopropanecarboxylate
• 英文别名: methyl (1R,2R)-1,2-diphenylcyclopropane-1-carboxylate
• CAS: 42333-04-0
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: YAOZVDIKXMRFBG-WBVHZDCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl 1,2-diphenylcyclopropanecarboxylate 在 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 以64%的产率得到rel-[(1S,2S)-1,2-diphenylcyclopropyl]methanol
  参考文献：
  名称：

  Tarwade, Vinod; Liu, Xiaozhong; Yan, Ni, Journal of the American Chemical Society, 2009, vol. 131, p. 5382 - 5383

  摘要：

  DOI：
• 作为产物：
  描述：

  a-叠氮基-苯乙酸甲酯 在 dirhodium(II) tetra((S)-N-(dodecylbenzenesulfonyl)prolinate) potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 13.0h， 生成 methyl 1,2-diphenylcyclopropanecarboxylate
  参考文献：
  名称：

  Dirhodium(II) Tetra(N-(dodecylbenzenesulfonyl)prolinate) Catalyzed Enantioselective Cyclopropenation of Alkynes

  摘要：

  [GRAPHICS]Dirhodium tetrakis((S)-N(dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) is an effective chiral catalyst for the enantioselective cyclopropenation of alkynes by methyl aryldiazoacetates.

  DOI：

  10.1021/ol049928c

文献信息

• Room Temperature Coupling of Aryldiazoacetates with Boronic Acids Enhanced by Blue Light Irradiation
  作者：Amanda F. Silva、Marco A. S. Afonso、Rodrigo A. Cormanich、Igor D. Jurberg

  DOI：10.1002/chem.201905812

  日期：2020.5.4

  visible-light-promoted photochemical protocol is reported for the coupling of aryldiazoacetates with boronic acids. This photochemical reaction shows great enhancement compared to the same protocol performed in the absence of light. Except for a few cases, the room temperature coupling in the dark (thermal process) generally does not work. When it does, it is likely to also involve free carbenes as key intermediates

  据报道可见光促进的光化学方案用于芳基重氮乙酸酯与硼酸的偶联。与没有光照的相同方案相比，这种光化学反应显示出极大的增强。除少数情况外，在黑暗（热过程）中的室温耦合通常不起作用。如果这样做的话，很可能还涉及到游离卡宾作为关键中间体。可替代地，光化学反应显示出广泛的范围，可以在空气中进行并且耐受各种各样的官能团。反应进化监测，DFT计算和控制实验已用于评估这种复杂机制的主要方面。具有生物活性的分子阿迪芬，苯那西嗪和阿普生已经被制备为合成应用的实例。
• Blue light-promoted photolysis of aryldiazoacetates
  作者：Igor D. Jurberg、Huw M. L. Davies

  DOI：10.1039/c8sc01165f

  日期：——

  Aryldiazoacetates can undergo photolysis under blue light irradiation (460–490 nm) at room temperature and under air in the presence of numerous trapping agents, such as styrene, carboxylic acids, amines, alkanes and arenes, thus providing a straighforward and general platform for their mild functionalization.

  芳基重氮乙酸酯可以在室温和空气中，在苯乙烯、羧酸、胺、烷烃和芳烃等多种捕集剂存在下，在蓝光照射（460-490 nm）下发生光解，从而为它们的合成提供了一个简单而通用的平台。轻度功能化。
• Enhancement of Cyclopropanation Chemistry in the Silver-Catalyzed Reactions of Aryldiazoacetates
  作者：Janelle L. Thompson、Huw M. L. Davies

  DOI：10.1021/ja069314y

  日期：2007.5.1

  AgSbF6 is an effective catalyst for the reactions of donor/acceptor substituted carbenoids and shows a very different reactivity profile from the traditional rhodium-catalyzed reactions. Most notably, cyclopropanation of sterically hindered alkenes is favorable, and products due to a Wolff rearrangement are not observed. Yields of products obtained are often high (54−96%) with excellent diastereoselectivity

  AgSbF6 是供体/受体取代类卡宾反应的有效催化剂，并且显示出与传统铑催化反应非常不同的反应特性。最值得注意的是，空间位阻烯烃的环丙烷化是有利的，并且没有观察到由于沃尔夫重排产生的产物。获得的产品的产率通常很高 (54-96%)，具有出色的非对映选择性 (>94% de)。
• Highly Stereoselective Carbon–Carbon Bond-forming Reactions on Cyclopropane Rings Using 1-(Methoxycarbonyl)cyclopropylzinc Bromides
  作者：Daichi Sakuma、Kenta Yamada、Kazuya Sasazawa、Yoshinori Nishii

  DOI：10.1246/cl.150085

  日期：2015.6.5

  Highly stereoselective Reformatsky reaction and Pd-catalyzed arylation using 1-(alkoxycarbonyl)cyclopropylzinc bromide proceeded to give the trans-adduct as the major product in good to high yields with good to excellent stereoselectivities.

  高立体选择性的Reformatsky反应和钯催化的芳基化反应，使用1-(烷氧基羧酸基)环丙基溴化锌，得到的反式加成物作为主要产物，产率较好到很高，立体选择性较好到优秀。
• Novel chiral dirhodium catalysts derived from aziridine and azetidine carboxylic acid for intermolecular cyclopropanation reactions with methyl phenyldiazoacetate
  作者：Wim A.J. Starmans、Lambertus Thijs、Binne Zwanenburg

  DOI：10.1016/s0040-4020(97)10322-2

  日期：1998.1

  Three new chiral dirhodium(II) tetracarboxylate catalysts, based on azetidine- and aziridine-2-carboxylic acid, were prepared. Their selectivities in the cyclopropanation reaction of methyl phenyldiazoacetate and olefins were determined in solvents of decreasing polarity and compared with those obtained with proline derived catalysts.

  制备了三种新的基于氮杂环丁烷-和氮丙啶-2-羧酸的手性四羧酸二铑（II）手性催化剂。在极性递减的溶剂中测定了它们在苯基重氮乙酸甲酯和烯烃的环丙烷化反应中的选择性，并将其与脯氨酸衍生的催化剂的选择性进行了比较。