[1-13C]-4-Phenylbutyronitrile | 166111-39-3

• 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: [1-13C]-4-Phenylbutyronitrile
• 英文别名: 4-phenyl(113C)butanenitrile
• CAS: 166111-39-3
• 化学式: C₁₀H₁₁N
• 分子量: 146.193
• InChiKey: ICMVGKQFVMTRLB-QBZHADDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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

• 作为反应物：
  描述：

  [1-13C]-4-Phenylbutyronitrile 在 盐酸 作用下， 生成 <1-13C>-4-Phenylbutyric acid
  参考文献：
  名称：

  5-环癸酮的跨环重排

  摘要：

  十三碳标记实验表明，酸催化的5-环癸酮重排为双环[4.4.0] -1（6）-癸烯-2-酮的反应机理与5-环癸酮的烯醇无关

  DOI：

  10.1016/s0040-4039(00)79277-x
• 作为产物：
  描述：

  1-溴-3-苯基丙烷 以95%的产率得到
  参考文献：
  名称：

  Wempe Michael F., Grunwell John R., J. Org. Chem, 60 (1995) N 9, S 2714-2720

  摘要：

  DOI：

文献信息

• Synthesis of [1-13C] and [1-15N] labelled DL-homophenylalanine via a key Neber rearrangement
  作者：Mark F. Oldfield、Nigel P. Botting

  DOI：10.1002/(sici)1099-1344(199801)41:1<29::aid-jlcr50>3.0.co;2-e

  日期：1998.1

  A synthetic route involving a key Neber rearrangement is described for the preparation of both [1-13C] and [1-15N] DL-homophenylalanine (2-amino-4-phenylbutanoic acid), using suitably labelled sodium cyanide as the source of the isotopic label. These compounds have been prepared for use in studies on the biosynthesis of phenylethyl glucosinolate in Brassica napus. 3-Phenylpropanaldoxime, the initial

  描述了一种涉及关键 Neber 重排的合成路线，用于制备 [1-13C] 和 [1-15N] DL-高苯丙氨酸（2-氨基-4-苯基丁酸），使用适当标记的氰化钠作为其来源同位素标签。这些化合物已制备用于研究甘蓝型油菜中苯乙基硫代葡萄糖苷的生物合成。3-苯基丙醛肟是由高苯丙氨酸形成的初始生物合成产物，也以 15N 标记形式制备。© 1998 John Wiley & Sons, Ltd.
• The Transannular Rearrangement of 5-Cyclodecynone
  作者：Michael F. Wempe、John R. Grunwell

  DOI：10.1021/jo00114a018

  日期：1995.5

  The acid-catalyzed rearrangement of 5-cyclodecynone (1) to bicyclo[4.4.0]-1(6)-decen-2-one (5) has been investigated via C-13 and deuterium labeling experiments, which showed that the transannular rearrangement proceeds by a mechanism not involving an enol of 5-cyclodecynone. Subjecting 5-cyclodecynone to NBS in ethyl ether resulted in the formation of a dibromooxetane 21 which arose from a bromo allylic alcohol 20 formed from 5-cyclodecynone and HBr. The chloro allylic alcohol 28 was formed from HCl and was subsequently converted to enone 5. Pathways were investigated using AM1 calculations. As a result, a modified mechanism consistent with all the experimental data is proposed for the acid-catalyzed rearrangement of 1 to 5.