[(E)-4-phenylbut-3-en-2-yl] pyridine-2-carboxylate | 1174917-21-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [(E)-4-phenylbut-3-en-2-yl] pyridine-2-carboxylate
• CAS: 1174917-21-5
• 化学式: C₁₆H₁₅NO₂
• 分子量: 253.301
• InChiKey: MFCSCKDCTHXJEE-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(E)-4-phenylbut-3-en-2-yl] pyridine-2-carboxylate 、 p-tolylethynyl-magnesium bromide 在 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 以84%的产率得到
  参考文献：
  名称：

  SN2-Selective allylic substitution of chiral γ-aryl substituted allylic picolinates with alkynylcopper reagents

  摘要：

  Substitution of gamma-aryl secondary allylic picolinates with alkynyl copper reagents was studied. The copper reagent, prepared from TMSC equivalent to CMgBr and CuBr center dot Me-25 in 2:1, was subjected to substitution of the picolinate derived from (E)-3-phenyl-1-methyl-2-propenyl alcohol at 0 degrees C for 1 h in THF to produce a mixture of alpha- and gamma-products and the alcohol in 67:20:13, while the reagent in 3 or 4:1 ratio gave the alpha-product with 90-91% selectivity. On the contrary, reaction in CH2Cl2-THF (6-8:1) at 0 degrees C for 1 h furnished the alpha-product with 99% regioselectivity. The effect of CH2Cl2 was also demonstrated with eight more examples. Furthermore, 99% inversion was determined by transformation to the literature compound and by chiral H PLC. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.08.051

文献信息

• SN2-Selective allylic substitution of chiral γ-aryl substituted allylic picolinates with alkynylcopper reagents
  作者：Qian Wang、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2010.08.051

  日期：2010.10

  Substitution of gamma-aryl secondary allylic picolinates with alkynyl copper reagents was studied. The copper reagent, prepared from TMSC equivalent to CMgBr and CuBr center dot Me-25 in 2:1, was subjected to substitution of the picolinate derived from (E)-3-phenyl-1-methyl-2-propenyl alcohol at 0 degrees C for 1 h in THF to produce a mixture of alpha- and gamma-products and the alcohol in 67:20:13, while the reagent in 3 or 4:1 ratio gave the alpha-product with 90-91% selectivity. On the contrary, reaction in CH2Cl2-THF (6-8:1) at 0 degrees C for 1 h furnished the alpha-product with 99% regioselectivity. The effect of CH2Cl2 was also demonstrated with eight more examples. Furthermore, 99% inversion was determined by transformation to the literature compound and by chiral H PLC. (C) 2010 Elsevier Ltd. All rights reserved.