Methyl 7-[2-(methoxymethoxy)-5-oxocyclopenten-1-yl]-6-methyl-6-nitroheptanoate | 150111-77-6

• 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: Methyl 7-[2-(methoxymethoxy)-5-oxocyclopenten-1-yl]-6-methyl-6-nitroheptanoate
• 英文别名: methyl 7-[2-(methoxymethoxy)-5-oxocyclopenten-1-yl]-6-methyl-6-nitroheptanoate
• CAS: 150111-77-6
• 化学式: C₁₆H₂₅NO₇
• 分子量: 343.377
• InChiKey: MPXSZTIKEUHMMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  24
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Methyl 7-[2-(methoxymethoxy)-5-oxocyclopenten-1-yl]-6-methyl-6-nitroheptanoate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Synthesis of PGB1 analogs by radical chain substitution reaction

  摘要：

  PGB1 analogues with functionalized or sulfur atom-containing alpha-side chains have been synthesized in several steps from 1,3-cyclopentanedione. Introduction of alpha- and omega-side chains into the PGB1 cyclopentenone skeleton has been accomplished by replacement of an allylic sulfonyl group in 3-substituted 2-[(phenylsulfonyl)methyl]-2-cyclopenten-1-one by stabilized carbanions or thiolate ions and Pd(0)-catalyzed cross-coupling reaction between the vinylic iodide moiety in 2-substituted 3-iodo-2-cyclopenten-1-ones and a vinyltin reagent or an alkyne, respectively. The former substitution reaction with stabilized carbanions has been confirmed to proceed via a radical chain mechanism of S(RN)1 type by investigating the effects of a radical scavenger and by the ESR studies. Further, comparison of the reduction potentials of substrates with those of products supports a single electron transfer mechanism.

  DOI：

  10.1021/jo00067a030
• 作为产物：
  描述：

  3-Hydroxy-2-<(phenylsulfonyl)methyl>-2-cyclopenten-1-one 在 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.5h， 生成 Methyl 7-[2-(methoxymethoxy)-5-oxocyclopenten-1-yl]-6-methyl-6-nitroheptanoate
  参考文献：
  名称：

  Synthesis of PGB1 analogs by radical chain substitution reaction

  摘要：

  PGB1 analogues with functionalized or sulfur atom-containing alpha-side chains have been synthesized in several steps from 1,3-cyclopentanedione. Introduction of alpha- and omega-side chains into the PGB1 cyclopentenone skeleton has been accomplished by replacement of an allylic sulfonyl group in 3-substituted 2-[(phenylsulfonyl)methyl]-2-cyclopenten-1-one by stabilized carbanions or thiolate ions and Pd(0)-catalyzed cross-coupling reaction between the vinylic iodide moiety in 2-substituted 3-iodo-2-cyclopenten-1-ones and a vinyltin reagent or an alkyne, respectively. The former substitution reaction with stabilized carbanions has been confirmed to proceed via a radical chain mechanism of S(RN)1 type by investigating the effects of a radical scavenger and by the ESR studies. Further, comparison of the reduction potentials of substrates with those of products supports a single electron transfer mechanism.

  DOI：

  10.1021/jo00067a030