diethyl 2-[(3R,5R)-5-hydroxy-2-methylocta-1,7-dien-3-yl]malonate | 1256634-38-4

• 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: diethyl 2-[(3R,5R)-5-hydroxy-2-methylocta-1,7-dien-3-yl]malonate
• 英文别名: diethyl 2-[(3R,5R)-5-hydroxy-2-methylocta-1,7-dien-3-yl]propanedioate
• CAS: 1256634-38-4
• 化学式: C₁₆H₂₆O₅
• 分子量: 298.379
• InChiKey: CQRXSGPRFBHLRU-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl 2-[(3R,5R)-5-hydroxy-2-methylocta-1,7-dien-3-yl]malonate 在 Hoveyda-Grubbs catalyst second generation 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以75%的产率得到diethyl 2-((1R,5R)-5-hydroxy-2-methylcyclohex-2-enyl)malonate
  参考文献：
  名称：

  Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone

  摘要：

  A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate (+/-)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.051
• 作为产物：
  描述：

  (R)-diethyl 2-(2-methyl-5-oxopent-1-en-3-yl)malonate 、 烯丙基三甲基硅烷 在 三氟化硼乙醚 、 水 、 碳酸氢钠 作用下， 以 二氯甲烷 、 四氢呋喃 为溶剂， 反应 15.0h， 以16%的产率得到(4R,6S)-ethyl 6-allyl-tetrahydro-2-oxo-4-(prop-1-en-2-yl)-2H-pyran-3-carboxylate
  参考文献：
  名称：

  Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone

  摘要：

  A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate (+/-)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.08.051

文献信息

• Synthesis of diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate by Pd-catalyzed intramolecular allylic alkylation. Stereoselective preparation of its optically homogeneous form from R-(−)-carvone
  作者：Raquel Galán-Fernández、David Clemente-Tejeda、Enrique del Río-Nieto、Francisco A. Bermejo

  DOI：10.1016/j.tet.2010.08.051

  日期：2010.10

  A new route to racemic diethyl 2-methyl-bicyclo[3.1.1]hept-2-ene-6,6-dicarboxylate (+/-)-1a by means of a palladium-catalyzed intramolecular allylic alkylation exercised on malonate-ester derivatives has been developed from R-(-)-carvone. The stereocontrolled synthesis of the enantiomerically pure (-)-1b by application of a six-step reactions sequence with a 28% overall yield from acetal 8, has been accomplished. (C) 2010 Elsevier Ltd. All rights reserved.