3-Methyl-N-hydroxypyrrolidine | 167971-75-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-Methyl-N-hydroxypyrrolidine
• 英文别名: hydroxy-3-methylpyrrolidin；4-methylpyrrolidinol；1-Hydroxy-3-methylpyrrolidine
• CAS: 167971-75-7
• 化学式: C₅H₁₁NO
• 分子量: 101.148
• InChiKey: LWCYKKRWFZZFMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Methyl-N-hydroxypyrrolidine 在 mercury(II) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-Methyl-1-pyrroline N-oxide 、 3-Methyl-1-pyrroline N-oxide
  参考文献：
  名称：

  A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

  摘要：

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

  DOI：

  10.1021/jo00120a016
• 作为产物：
  描述：

  2-甲基-1,4-丁二醇 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.25h， 生成 3-Methyl-N-hydroxypyrrolidine
  参考文献：
  名称：

  A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine

  摘要：

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

  DOI：

  10.1021/jo00120a016

文献信息

• The Absolute Configuration of 3-Methylpyrrolidine Alkaloids from Poison Glands of Ants Leptothoracini (Myrmicinae)
  作者：Robert Koob、Christiane Rudolph、Hans Jiirgen Veith

  DOI：10.1002/hlca.19970800124

  日期：1997.2.10

  The absolute configuration of 3-methylpyrrolidine alkaloids isolated from the poison gland of ants Leptothoracini was determined as (3R). The enantiomeric separation by chiral gas chromatography and unambiguous structural assignment of the target compounds are described.

  从蚂蚁Leptothoracini的毒腺分离出的3-甲基吡咯烷生物碱的绝对构型确定为（3 R）。描述了通过手性气相色谱法的对映体分离和目标化合物的明确结构分配。
• A Five-Membered Enantiopure Cyclic Nitrone from Malic Acid by Regioselective Oxidation of Cyclic Hydroxylamine. Synthesis of (1S,7S,8aR)-Octahydro-1,7-dihydroxyindolizine
  作者：Stefano Cicchi、Andrea Goti、Alberto Brandi

  DOI：10.1021/jo00120a016

  日期：1995.7

  The chiral optically pure five-membered 3-tert-butoxy-1-pyrroline N-oxide (1) was synthesized by a convenient five-step procedure from diethyl L-malate. The key step is the regioselective HgO dehydrogenation of the N-hydroxypyrrolidine 6 obtained by double-nucleophilic displacement of a (bis)mesylate with hydroxylamine. A rationalization of the observed regioselectivity of the oxidation by studying the oxidation of a deuterated N-hydroxypyrrolidine 20 is reported. Nitrone 1 has been applied to the synthesis of a new (1S,7S,8aR)-1,7-dihydroxyindolizidine (28) via 1,3-dipolar cycloaddition strategies.

表征谱图