4-benzyl-4-methylmorpholinium [(1S)-(1β,2α,3β)-(+)-3-methyl-2-(nitromethyl)-5-oxocyclopentyl]acetate | 1346236-54-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-benzyl-4-methylmorpholinium [(1S)-(1β,2α,3β)-(+)-3-methyl-2-(nitromethyl)-5-oxocyclopentyl]acetate
• CAS: 1346236-54-1
• 化学式: C₉H₁₂NO₅*C₁₂H₁₈NO
• 分子量: 406.479
• InChiKey: QGBUMGSHZOXBKP-KISWOZELSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  0.91
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  109.57
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  N-benzyl-N-methylmorpholinium chloride 、 [1S-(1β,2α,3β)]-(+)-3-甲基-2-(硝基甲基)-5-氧代环戊烷乙酸 在 potassium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 4-benzyl-4-methylmorpholinium [(1S)-(1β,2α,3β)-(+)-3-methyl-2-(nitromethyl)-5-oxocyclopentyl]acetate
  参考文献：
  名称：

  Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran

  摘要：

  It is demonstrated that a relatively small amount of IL (IL = ionic liquid) can dramatically affect conversion in the Heck arylation of 2,3-dihydrofuran with iodobenzene, catalyzed by Pd(OAc)(2) in DMF as a solvent. In all reactions, 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product, and conversion increased even up to 10 times when pyridinium salts with 1-butyl-4-methylpyridinium cation were applied. In a 1:1 mixture of DMF and H2O as solvent, the addition of ILs led to a remarkable deactivation of the catalyst, and this effect was most visible in the presence of imidazolium salts containing a 1-buty1-3-methylimidazolium cation. The influence of the anionic part of ILs on the reaction course was tested using a series of morpholinium salts and, depending on the anion, conversion varied from 0.4% to even 100%. When morpholinium salts with chiral anions were used, e.e. values of up to 10% were obtained, which is the highest value for the Heck reaction involving IL as a chirality source. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2011.09.038
• 作为试剂：
  描述：

  2,3-二氢呋喃 、 碘苯 在 4-benzyl-4-methylmorpholinium [(1S)-(1β,2α,3β)-(+)-3-methyl-2-(nitromethyl)-5-oxocyclopentyl]acetate 、 palladium diacetate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 2-苯基-4,5-二氢呋喃 、 (-)-(S)-2,5-dihydro-2-phenylfuran 、 (S)-2-phenyl-2,3-dihydrofuran 、 呋喃,2,3-二氢-2-苯基-,(R)- 、 (R)-2-phenyl-2,5-dihydrofuran
  参考文献：
  名称：

  Effect of chiral ionic liquids on palladium-catalyzed Heck arylation of 2,3-dihydrofuran

  摘要：

  It is demonstrated that a relatively small amount of IL (IL = ionic liquid) can dramatically affect conversion in the Heck arylation of 2,3-dihydrofuran with iodobenzene, catalyzed by Pd(OAc)(2) in DMF as a solvent. In all reactions, 2-phenyl-2,3-dihydrofuran (3) was obtained as the main product, and conversion increased even up to 10 times when pyridinium salts with 1-butyl-4-methylpyridinium cation were applied. In a 1:1 mixture of DMF and H2O as solvent, the addition of ILs led to a remarkable deactivation of the catalyst, and this effect was most visible in the presence of imidazolium salts containing a 1-buty1-3-methylimidazolium cation. The influence of the anionic part of ILs on the reaction course was tested using a series of morpholinium salts and, depending on the anion, conversion varied from 0.4% to even 100%. When morpholinium salts with chiral anions were used, e.e. values of up to 10% were obtained, which is the highest value for the Heck reaction involving IL as a chirality source. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.apcata.2011.09.038