methyl (S,E)-2-methyl-4-phenylbut-3-enoate | 182699-65-6

• 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: methyl (S,E)-2-methyl-4-phenylbut-3-enoate
• 英文别名: methyl (E,2S)-2-methyl-4-phenylbut-3-enoate
• CAS: 182699-65-6
• 化学式: C₁₂H₁₄O₂
• 分子量: 190.242
• InChiKey: KPZBEVBLJYUANV-DDXVTDLHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 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 (S,E)-2-methyl-4-phenylbut-3-enoate 生成 (3S,6R,10R,13E,16S)-10-[(3-chloro-4-methoxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-[(E,2S)-4-phenylbut-3-en-2-yl]-1,4-dioxa-8,11-diazacyclohexadec-13-ene-2,5,9,12-tetrone
  参考文献：
  名称：

  Total Synthesis of Cryptophycins via a Chemoenzymatic Approach

  摘要：

  A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

  DOI：

  10.1021/jo960972i
• 作为产物：
  描述：

  (E)-2-甲基-4-苯基-3-丁烯酸甲酯 在 sodium azide 、 phosphate buffer 作用下， 以 乙醚 、 水 为溶剂， 反应 120.08h， 生成 methyl (S,E)-2-methyl-4-phenylbut-3-enoate
  参考文献：
  名称：

  Total Synthesis of Cryptophycins via a Chemoenzymatic Approach

  摘要：

  A highly convergent synthesis of cryptophycins in their enantiomerically-pure forms was achieved. Our strategy consists of the synthesis of the two units 3 and 4 and linking them together to form the macrocyclic ring. The upper unit 3 was prepared from 10 in four steps, and the lower unit 4 was prepared from 20 in three steps. Enantioselective biocatalytic methodology was used to prepare the requisite chiral building blocks, (R)-11 and (R)-19. The stereochemical versatility of this synthetic approach is demonstrated by the synthesis of cryptophycin A and the four diastereomers of cryptophycin C.

  DOI：

  10.1021/jo960972i

文献信息

• Enantioselective Intermolecular Pd-Catalyzed Hydroalkylation of Acyclic 1,3-Dienes with Activated Pronucleophiles
  作者：Nathan J. Adamson、Katherine C. E. Wilbur、Steven J. Malcolmson

  DOI：10.1021/jacs.7b13300

  日期：2018.2.28

  We report a highly enantioselective Pd-PHOX-catalyzed intermolecular hydroalkylation of acyclic 1,3-dienes. Meldrum's acid derivatives and other activated C-pronucleophiles, such as β-diketones and malononitriles, react with a variety of aryl- and alkyl-substituted dienes in ≤20 h at room temperature. The coupled products, obtained in up to 96% yield and 97.5:2.5 er, are easily transformed into useful

  我们报道了一种高度对映选择性的 Pd-PHOX 催化的无环 1,3-二烯的分子间加氢烷基化反应。Meldrum 的酸衍生物和其他活化的 C-亲核试剂，例如 β-二酮和丙二腈，可在室温下 ≤20 小时内与各种芳基和烷基取代的二烯反应。偶联产物的产率高达 96%，比例为 97.5:2.5，很容易转化为下游合成有用的化学结构单元。