Isopropyl 2-pyrrolylacetate | 157071-48-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Isopropyl 2-pyrrolylacetate
• 英文别名: (1H-pyrrol-2-yl)acetic acid isopropyl ester；Isopropyl 1H-pyrrol-2-ylacetate；propan-2-yl 2-(1H-pyrrol-2-yl)acetate
• CAS: 157071-48-2
• 化学式: C₉H₁₃NO₂
• mdl: MFCD18452954
• 分子量: 167.208
• InChiKey: YDFWVTIOXQLWNF-UHFFFAOYSA-N

物化性质

• 沸点：
  257.5±15.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Isopropyl 2-pyrrolylacetate 在 sodium hydroxide 、 草酰氯 、 四丁基溴化铵 、 potassium carbonate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 85.25h， 生成 酮咯酸
  参考文献：
  名称：

  Highly Efficient Synthesis of Alkyl Pyrrolylacetates and Dialkyl Pyrrolylmalonates

  摘要：

  N-Pyrrolylmagnesium halides (1,2) react with alkyl bromoacetates (3a-d) in THF solution to give alkyl 2-pyrrolylacetates (5a-d) in good yields and with very high positional selectivity (C-2:C-3 greater than or equal to 25). The high regioselectivity is rationalized in terms of an increased propinquity between C-2 and the bromoacetate methylene group as a consequence of coordination between magnesium and the carbonyl oxygen of the alkylating agent, (2,5-Dimethylpyrrol-N-yl)magnesium chloride (9) and isopropyl bromoacetate (3c) gave the 3-pyrrolylacetate 10 exclusively. Alkoxycarbonylation of the dianions of the above alkyl pyrrolylacetates with alkyl chloroformates gave the corresponding dialkyl pyrrolylmalonates, two of which (16a and 19) were transformed into the dialkyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates (22 and 20, respectively) with 1,2-dichloroethane under phase transfer conditions. Compound 20 was converted into the powerful nonaddicting analgesic ketorolac (21).

  DOI：

  10.1021/jo00097a025
• 作为产物：
  描述：

  (4-methoxypyrrolidin-2-ylidene)acetic acid isopropyl ester 以 1,4-二氧六环 为溶剂， 反应 24.0h， 以100%的产率得到Isopropyl 2-pyrrolylacetate
  参考文献：
  名称：

  甲硅烷基醚和1,3-双-甲硅烷基烯醇醚与1-叠氮基-2,2-二甲氧基乙烷的缩合反应及其后的还原环化反应，合成2-亚烷基吡咯烷，吡咯和吲哚

  摘要：

  1，3-双甲硅烷基烯醇醚与1-叠氮基-2，2-二甲氧基乙烷的缩合和随后的还原环化使得各种2-亚烷基-4-甲氧基吡咯烷的区域和非对映选择性合成成为可能。甲醇的热消除导致官能化吡咯的形成。类似地，制备了2,3,3a，4,5,6-六氢-2,3-苯并吡咯并转化为4,5,6,7-四氢-2,3-苯并吡咯。相反，用三氟乙酸处理2-亚烷基亚吡咯烷导致通过[4 + 2]环加成形成吲哚并随后挤出氮原子。

  DOI：

  10.1021/jo047856x

文献信息

• Highly Efficient Synthesis of Alkyl Pyrrolylacetates and Dialkyl Pyrrolylmalonates
  作者：George C. Schloemer、Robert Greenhouse、Joseph M. Muchowski

  DOI：10.1021/jo00097a025

  日期：1994.9

  N-Pyrrolylmagnesium halides (1,2) react with alkyl bromoacetates (3a-d) in THF solution to give alkyl 2-pyrrolylacetates (5a-d) in good yields and with very high positional selectivity (C-2:C-3 greater than or equal to 25). The high regioselectivity is rationalized in terms of an increased propinquity between C-2 and the bromoacetate methylene group as a consequence of coordination between magnesium and the carbonyl oxygen of the alkylating agent, (2,5-Dimethylpyrrol-N-yl)magnesium chloride (9) and isopropyl bromoacetate (3c) gave the 3-pyrrolylacetate 10 exclusively. Alkoxycarbonylation of the dianions of the above alkyl pyrrolylacetates with alkyl chloroformates gave the corresponding dialkyl pyrrolylmalonates, two of which (16a and 19) were transformed into the dialkyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylates (22 and 20, respectively) with 1,2-dichloroethane under phase transfer conditions. Compound 20 was converted into the powerful nonaddicting analgesic ketorolac (21).
• Synthesis of 2-Alkylidenepyrrolidines, Pyrroles, and Indoles by Condensation of Silyl Enol Ethers and 1,3-Bis-Silyl Enol Ethers with 1-Azido-2,2-dimethoxyethane and Subsequent Reductive Cyclization
  作者：Esen Bellur、Helmar Görls、Peter Langer

  DOI：10.1021/jo047856x

  日期：2005.6.1

  The condensation of 1,3-bis-silyl enol ethers with 1-azido-2,2-dimethoxyethane and subsequent reductive cyclization allowed an efficient regio- and diastereoselective synthesis of a variety of 2-alkylidene-4-methoxypyrrolidines. The thermal elimination of methanol resulted in the formation of functionalized pyrroles. Similarly, 2,3,3a,4,5,6-hexahydro-2,3-benzopyrroles were prepared and transformed

  1，3-双甲硅烷基烯醇醚与1-叠氮基-2，2-二甲氧基乙烷的缩合和随后的还原环化使得各种2-亚烷基-4-甲氧基吡咯烷的区域和非对映选择性合成成为可能。甲醇的热消除导致官能化吡咯的形成。类似地，制备了2,3,3a，4,5,6-六氢-2,3-苯并吡咯并转化为4,5,6,7-四氢-2,3-苯并吡咯。相反，用三氟乙酸处理2-亚烷基亚吡咯烷导致通过[4 + 2]环加成形成吲哚并随后挤出氮原子。