ethyl (4Z)-2-diazo-3-oxo-6-(tetrahydro-pyran-2-yloxy)hex-4-enoate | 870673-70-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl (4Z)-2-diazo-3-oxo-6-(tetrahydro-pyran-2-yloxy)hex-4-enoate
• 英文别名: ethyl (Z)-2-diazo-6-(oxan-2-yloxy)-3-oxohex-4-enoate
• CAS: 870673-70-4
• 化学式: C₁₃H₁₈N₂O₅
• 分子量: 282.296
• InChiKey: UUFJZZBXAGOAJS-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.8
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl (4Z)-2-diazo-3-oxo-6-(tetrahydro-pyran-2-yloxy)hex-4-enoate 在 dirhodium tetraacetate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以82%的产率得到(1R,5S)-2-Oxo-5-(tetrahydro-pyran-2-yloxy)-cyclopent-3-enecarboxylic acid ethyl ester
  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：

  4-(tetrahydropyran-2-yloxy)-but-2-ynal 在 Lindlar's catalyst manganese(IV) oxide 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 35.5h， 生成 ethyl (4Z)-2-diazo-3-oxo-6-(tetrahydro-pyran-2-yloxy)hex-4-enoate
  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

文献信息

• 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
  作者：Guisheng Deng、Baihua Xu、Jianbo Wang

  DOI：10.1016/j.tet.2005.05.106

  日期：2005.11

  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.