(R)-5-[(RS)-2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-enone | 1256634-24-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-5-[(RS)-2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-enone
• 英文别名: 2-Cyclohexen-1-one, 5-[2-(hydroxymethyl)-2-oxiranyl]-2-methyl-, (5R)-；(5R)-5-[2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-en-1-one
• CAS: 1256634-24-8
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: KCUIHGXGKBZLLY-HNHGDDPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-5-[(RS)-2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-enone 在 二氯二茂钛 、 1,4-环己二烯 、 锌 、 disodium hydrogenphosphate 作用下， 以 四氢呋喃 为溶剂， 以85%的产率得到(R)-5-(1,3-dihydroxypropan-2-yl)-2-methylcyclohex-2-enone
  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)-5-(3-hydroxyprop-1-en-2-yl)-2-methylcyclohex-2-enone 在 叔丁基过氧化氢 、 bis(acetylacetonate)oxovanadium 作用下， 以 癸烷 、 甲苯 为溶剂， 以60%的产率得到(R)-5-[(RS)-2-(hydroxymethyl)oxiran-2-yl]-2-methylcyclohex-2-enone
  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.