(-)-trans-2-phenylcyclopropanecarbonitrile | 58641-88-6

• 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: (-)-trans-2-phenylcyclopropanecarbonitrile
• 英文别名: (1R,2R)-2-phenyl-1-cyclopropanenitrile；2-phenylcyclopropanecarbonitrile；trans-2-Phenyl-cyclopropancarbonsaeure-nitril；trans-2-Phenyl-cyclopropancarbonitril；trans-1-Cyan-2-phenyl-cyclopropan；Cyclopropanecarbonitrile, 2-phenyl-, trans-；(1R,2R)-2-phenylcyclopropane-1-carbonitrile
• CAS: 58641-88-6
• 化学式: C₁₀H₉N
• mdl: MFCD00019213
• 分子量: 143.188
• InChiKey: KUCVFITUDJTMFA-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  肉桂腈 生成 (-)-trans-2-phenylcyclopropanecarbonitrile
  参考文献：
  名称：

  BORNE R. F.; FORRESTER M. L.; WATERS I. W., J. MED. CHEM. , 1977, 20, NO 6, 771-776

  摘要：

  DOI：

文献信息

• A Practical and Controllable Enantioselective Synthesis of 2-Phenyl-1-cyclopropanecarboxylates via a Camphor-Derived Sulfonium Ylide
  作者：Zhi-Zhen Huang、Kun Huang

  DOI：10.1055/s-2005-869852

  日期：——

  We have developed a practical and controllable enantio­selective synthesis of 2-phenyl-1-cyclopropane-carboxylates via camphor-derived sulfonium ylide. The procedure has many advantages such as cheap starting materials, facile synthetic procedures, good yields, excellent diastereoselectivities and high enantioselectivities.

  我们开发出了一种通过樟脑衍生的醯化锍对 2-苯基-1-环丙烷羧酸酯进行对映选择性合成的实用可控方法。该方法具有许多优点，如起始原料便宜、合成过程简便、产率高、非对映选择性好和对映选择性高。
• Fe-Catalyzed Direct Synthesis of Nitriles from Carboxylic Acids with Electron-Deficient <i>N</i>-Cyano-<i>N</i>-aryl–arylsulfonamide
  作者：Guodong Zhang、Chengyu Zhang、Ye Tian、Feng Chen

  DOI：10.1021/acs.orglett.2c04185

  日期：2023.2.17

  Established carboxylic acids to nitriles conversion methods suffer from expensive catalysts, tedious steps, high temperatures (>200 °C), high pressure, or a narrow substrate range. Herein, we demonstrate a concise and efficient access to diverse nitrile compounds from ubiquitous carboxylic acids with electron-deficient N-cyano-N-aryl–arylsulfonamide (NCAS) in moderate to excellent yields. This strategy

  已建立的将羧酸转化为腈类的方法存在昂贵的催化剂、繁琐的步骤、高温 (>200 °C)、高压或窄底物范围等问题。在此，我们展示了一种从普遍存在的羧酸和缺电子的N-氰基-N-芳基-芳基磺酰胺 (NCAS) 中以中等到优异的收率从普遍存在的羧酸中简明有效地获取多种腈化合物的途径。该策略由廉价的铁催化剂促进，并且通常与伯、仲、叔和芳基羧酸以及各种官能团相容。
• Nucleophilic Carbenes Derived from Dichloromethane
  作者：Mingxin Liu、Nguyen Le、Christopher Uyeda

  DOI：10.1002/anie.202308913

  日期：2023.10.16

  Nickel catalysts promote cyclopropanation reactions of electron-deficient alkenes using dichloromethane as a methylene source. An asymmetric variant using a chiral pyridine-bis(oxazoline) ligand provides access to pharmaceutically relevant 2-aryl cyclopropyl carboxylates in highly enantioenriched form. The proposed mechanism involves the formation of a nucleophilic nickel carbene that reacts by a

  镍催化剂使用二氯甲烷作为亚甲基源，促进缺电子烯烃的环丙烷化反应。使用手性吡啶-双（恶唑啉）配体的不对称变体提供了高度对映体富集形式的药学相关的 2-芳基环丙基羧酸盐。所提出的机制涉及形成亲核镍卡宾，该卡宾通过 [2+2] -环加成/C-C 还原消除途径反应。
• Macroporous chiral ruthenium porphyrin polymers: a new solid-phase material used as a device for catalytic asymmetric carbene transfer
  作者：Yann Ferrand、Paul Le Maux、Gérard Simonneaux

  DOI：10.1016/j.tetasy.2005.10.021

  日期：2005.11

  A chiral ruthenium porphyrin complex, functionalized with four vinyl groups, has been polymerized with styrene, divinylbenzene (or ethylene glycol dimethacrylate) to obtain supported ruthenium complexes. The asymmetric addition of ethyl diazoacetate (or diazoacetonitrile) to styrene derivatives was carried out by using these polymers as catalysts. The reaction proceeded under mild conditions and gave trans-cyclopropanes with good enantiomeric excess (up to 90%). (c) 2005 Elsevier Ltd. All rights reserved.

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