2-(2-phenylethyl)-2-allylmalononitrile | 606148-73-6

• 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: 2-(2-phenylethyl)-2-allylmalononitrile
• 英文别名: 2-(2-Phenylethyl)-2-prop-2-enylpropanedinitrile；2-(2-phenylethyl)-2-prop-2-enylpropanedinitrile
• CAS: 606148-73-6
• 化学式: C₁₄H₁₄N₂
• 分子量: 210.279
• InChiKey: IQZLXRGNZVCHHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  406.9±45.0 °C(Predicted)
• 密度：
  1.034±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-phenylethyl)-2-allylmalononitrile 在 Rhodococcus sp. CGMCC 0497 作用下， 反应 120.0h， 生成 (2R)-2-cyano-2-allyl-4-phenylbutanamide 、 (2S)-2-cyano-2-allyl-4-phenylbutanamide
  参考文献：
  名称：

  Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

  摘要：

  A new application of nitrile-converting enzymes in the synthesis of optically active alpha,alpha-disubstituted-alpha-cyanoacetamides from alpha,alpha-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral alpha,alpha-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00456-7
• 作为产物：
  描述：

  2-(2-苯基乙基)丙二腈 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-(2-phenylethyl)-2-allylmalononitrile
  参考文献：
  名称：

  Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

  摘要：

  A new application of nitrile-converting enzymes in the synthesis of optically active alpha,alpha-disubstituted-alpha-cyanoacetamides from alpha,alpha-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral alpha,alpha-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(03)00456-7

文献信息

• Iron-catalyzed remote functionalization of inert C(sp³)–H bonds of alkenes <i>via</i> 1,<i>n</i>-hydrogen-atom-transfer by C-centered radical relay
  作者：Kang-Jie Bian、Yan Li、Kai-Fan Zhang、Yan He、Tian-Rui Wu、Cheng-Yu Wang、Xi-Sheng Wang

  DOI：10.1039/d0sc03987j

  日期：——

  alternative approach to traditional C–H activation that often involved harsh conditions, and vicinal or primary C–H functionalization, radical relay offers a solution to these long-held problems. Enabled by 1,n (n = 5, 6)-hydrogen atom transfer (HAT), we use a most prevalent moiety, alkene, as the precursor to an sp3 C-centered radical to promote selective cleavage of inert C(sp3)–H bonds for the generation

  作为传统C–H激活的替代方法，它通常涉及恶劣的条件以及附近或主要的C–H功能化，自由基中继为这些长期存在的问题提供了解决方案。通过1，n（n = 5，6）-氢原子转移（HAT）启用，我们使用最普遍的部分烯烃作为sp 3 C中心自由基的前体，以促进惰性C（sp 3的选择性裂解））–H键可生成叠氮基三氟甲基化分子。在反应中观察到温和的条件，广阔的范围和出色的区域选择性控制（> 20：1）。氘标记研究揭示了转化的动力学特征并验证了直接1，n-HAT途径。这种以C为中心的自由基中继的关键是铁起着自由基引发剂和终止剂的双重作用，通过叠氮基-配体转移通过自由基氧化来掺入叠氮化物功能。该方法和随后的衍生化有望快速合成含CF 3的有机叠氮化物，γ-内酰胺和三唑，这些被广泛用于设计新的荧光标签和功能材料。
• Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497
  作者：Zhong-Liu Wu、Zu-Yi Li

  DOI：10.1016/s0957-4166(03)00456-7

  日期：2003.8

  A new application of nitrile-converting enzymes in the synthesis of optically active alpha,alpha-disubstituted-alpha-cyanoacetamides from alpha,alpha-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral alpha,alpha-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods. (C) 2003 Elsevier Ltd. All rights reserved.