(E)-2-Diazo-4-phenyl-but-3-enoic acid (Z)-penta-2,4-dienyl ester | 255384-70-4

• 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: (E)-2-Diazo-4-phenyl-but-3-enoic acid (Z)-penta-2,4-dienyl ester
• 英文别名: [(2Z)-penta-2,4-dienyl] (E)-2-diazo-4-phenylbut-3-enoate
• CAS: 255384-70-4
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: FWPZEOJVBXXJRF-NNLZZCHTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  28.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-Diazo-4-phenyl-but-3-enoic acid (Z)-penta-2,4-dienyl ester 在 Rh₂[(N-(4-dodecylphenyl)sulfonyl)-(S)-prolinate]4 作用下， 以 正己烷 为溶剂， 反应 1.0h， 生成 (1R,5S,6R)-1-((E)-Styryl)-6-vinyl-3-oxa-bicyclo[3.1.0]hexan-2-one 、 (1S,5R,6S)-1-((E)-Styryl)-6-vinyl-3-oxa-bicyclo[3.1.0]hexan-2-one
  参考文献：
  名称：

  Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement Sequence

  摘要：

  The asymmetric induction in the intramolecular cyclopropanations of allyl vinyldiazoacetates catalyzed by tetrakis[N-[4-dodecylphenyl)sulfonyl]-(S)-prolinato] dirhodium [Rh-2(S-DOSP)(4)] is very dependent on the allyl substitution pattern. The reactions of cis-alkenes result in much higher asymmetric induction than trans-alkenes while the highest enantioselectivity was obtained with a disubstituted terminal alkene. The intramolecular cyclopropanation of dienylmethyl vinyldiazoacetates results in the synthesis of fused cycloheptadiene ring systems with full control of relative stereochemistry and variable enantioselectivity. The synthetic utility of this process was demonstrated by a short synthesis of 5-epi-tremulenolide in 93% ee.

  DOI：

  10.1021/jo990888d
• 作为产物：
  描述：

  反-苯乙烯乙酸 在 4-二甲氨基吡啶 、 4-乙酰氨基苯磺酰叠氮 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 (E)-2-Diazo-4-phenyl-but-3-enoic acid (Z)-penta-2,4-dienyl ester
  参考文献：
  名称：

  Enantioselective Synthesis of Fused Cycloheptadienes by a Tandem Intramolecular Cyclopropanation/Cope Rearrangement Sequence

  摘要：

  The asymmetric induction in the intramolecular cyclopropanations of allyl vinyldiazoacetates catalyzed by tetrakis[N-[4-dodecylphenyl)sulfonyl]-(S)-prolinato] dirhodium [Rh-2(S-DOSP)(4)] is very dependent on the allyl substitution pattern. The reactions of cis-alkenes result in much higher asymmetric induction than trans-alkenes while the highest enantioselectivity was obtained with a disubstituted terminal alkene. The intramolecular cyclopropanation of dienylmethyl vinyldiazoacetates results in the synthesis of fused cycloheptadiene ring systems with full control of relative stereochemistry and variable enantioselectivity. The synthetic utility of this process was demonstrated by a short synthesis of 5-epi-tremulenolide in 93% ee.

  DOI：

  10.1021/jo990888d