(E,E)-(hexa-2,4-dienyl)-2-diazo-3-oxo-butyrate | 860480-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E,E)-(hexa-2,4-dienyl)-2-diazo-3-oxo-butyrate
• 英文别名: [(2E,4E)-hexa-2,4-dienyl] 2-diazo-3-oxobutanoate
• CAS: 860480-96-2
• 化学式: C₁₀H₁₂N₂O₃
• 分子量: 208.217
• InChiKey: XCSBSBDNPJNTCG-VNKDHWASSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  45.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E,E)-(hexa-2,4-dienyl)-2-diazo-3-oxo-butyrate 在 [Rh₂{(S)-N-phthaloyl-tert-leucinate}4] 臭氧 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 32.0h， 生成 (R)-(+)-甲基丁二酸
  参考文献：
  名称：

  Enantioselective intramolecular cyclopropanation of allyl 2-diazo-3-silanyloxybut-3-enoates

  摘要：

  The performance of the [Rh-2{(S)-ntt}(4)]-catalyst in comparison to [Rh-2{(S)-ptt}(4)] and [Rh-2{(S)-dosp},(4)] has been examined with allyl 2-diazo-3-silanvloxybut-3-enoates. The best results were obtained with [Rh-2{(S)-ptt}(4)], where enantioselectivity culminated at 89% ee at -78 degrees C. [Rh-2{(S)-ntt}(4)] was slightly less selective, while [Rh-2{(S)-dosp}(4)] was found less suitable for these substrates. However, even the results obtained with [Rh-2{(S)-pttl}(4)] are much less satisfactory than those for the intramolecular cyclopropanation of allyl diazoacetates in the presence of [Rh-2{(S)-mepy}(4)]. (c) 2005 Elsevier Ltd. Ail rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.006
• 作为产物：
  描述：

  (E,E)-(hexa-2,4-dienyl)-3-oxo-butyrate 在 4-乙酰氨基苯磺酰叠氮 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以91%的产率得到(E,E)-(hexa-2,4-dienyl)-2-diazo-3-oxo-butyrate
  参考文献：
  名称：

  Enantioselective intramolecular cyclopropanation of allyl 2-diazo-3-silanyloxybut-3-enoates

  摘要：

  The performance of the [Rh-2{(S)-ntt}(4)]-catalyst in comparison to [Rh-2{(S)-ptt}(4)] and [Rh-2{(S)-dosp},(4)] has been examined with allyl 2-diazo-3-silanvloxybut-3-enoates. The best results were obtained with [Rh-2{(S)-ptt}(4)], where enantioselectivity culminated at 89% ee at -78 degrees C. [Rh-2{(S)-ntt}(4)] was slightly less selective, while [Rh-2{(S)-dosp}(4)] was found less suitable for these substrates. However, even the results obtained with [Rh-2{(S)-pttl}(4)] are much less satisfactory than those for the intramolecular cyclopropanation of allyl diazoacetates in the presence of [Rh-2{(S)-mepy}(4)]. (c) 2005 Elsevier Ltd. Ail rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.006

文献信息

• Enantioselective intramolecular cyclopropanation of allyl 2-diazo-3-silanyloxybut-3-enoates
  作者：Paul Müller、Yves F. Allenbach、Stéfane Grass

  DOI：10.1016/j.tetasy.2005.04.006

  日期：2005.6

  The performance of the [Rh-2(S)-ntt}(4)]-catalyst in comparison to [Rh-2(S)-ptt}(4)] and [Rh-2(S)-dosp},(4)] has been examined with allyl 2-diazo-3-silanvloxybut-3-enoates. The best results were obtained with [Rh-2(S)-ptt}(4)], where enantioselectivity culminated at 89% ee at -78 degrees C. [Rh-2(S)-ntt}(4)] was slightly less selective, while [Rh-2(S)-dosp}(4)] was found less suitable for these substrates. However, even the results obtained with [Rh-2(S)-pttl}(4)] are much less satisfactory than those for the intramolecular cyclopropanation of allyl diazoacetates in the presence of [Rh-2(S)-mepy}(4)]. (c) 2005 Elsevier Ltd. Ail rights reserved.