ethyl 2-diazo-3-hydroxynon-4-ynoate | 870673-56-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 2-diazo-3-hydroxynon-4-ynoate
• CAS: 870673-56-6
• 化学式: C₁₁H₁₆N₂O₃
• 分子量: 224.26
• InChiKey: CDYWUTVJIAWWFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 2-diazo-3-hydroxynon-4-ynoate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以70%的产率得到ethyl 3-oxonon-4-ynoate
  参考文献：
  名称：

  A new method for the synthesis of 2-cyclopenten-1-one-5-carboxylic ester derivatives via Rh2(OAc)4-mediated intramolecular C–H insertion reaction of 4Z-β-vinyl-α-diazo β-ketoesters

  摘要：

  2-Cyclopenten-1-one-5-carboxylic ester derivatives 14 are synthesized in a four- step-reaction sequence starting from alkynyl aldehydes 9 via 4Z-beta-vinyl-alpha-diazo beta-ketoesters intermediate 8. The synthetic method for 8 is described. When the delta substituent is an alkyl group, Rh(Il)-mediated decomposition of the diazo compounds 8 led to an intramolecular C-H insertion to afford 2-cyclopenten-1-one-5-carboxylic ester derivatives 14 in high yields. When the delta substituent is an aryl group, 2-hydroxynaphthoate 15 is obtained exclusively. In both cases, no Wolff rearrangement product was observed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.106
• 作为产物：
  描述：

  重氮乙酸乙酯 、 2-庚炔醛 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以59%的产率得到ethyl 2-diazo-3-hydroxynon-4-ynoate
  参考文献：
  名称：

  A new method for the synthesis of 2-cyclopenten-1-one-5-carboxylic ester derivatives via Rh2(OAc)4-mediated intramolecular C–H insertion reaction of 4Z-β-vinyl-α-diazo β-ketoesters

  摘要：

  2-Cyclopenten-1-one-5-carboxylic ester derivatives 14 are synthesized in a four- step-reaction sequence starting from alkynyl aldehydes 9 via 4Z-beta-vinyl-alpha-diazo beta-ketoesters intermediate 8. The synthetic method for 8 is described. When the delta substituent is an alkyl group, Rh(Il)-mediated decomposition of the diazo compounds 8 led to an intramolecular C-H insertion to afford 2-cyclopenten-1-one-5-carboxylic ester derivatives 14 in high yields. When the delta substituent is an aryl group, 2-hydroxynaphthoate 15 is obtained exclusively. In both cases, no Wolff rearrangement product was observed. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.05.106