1-(1,1-dimethylethoxycarbonyl)-3-(hydroxymethyl)pyrrole | 175689-35-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 1-(1,1-dimethylethoxycarbonyl)-3-(hydroxymethyl)pyrrole
• 英文别名: 1-BOC-3-hydroxymethylpyrrole；1-Boc-1H-pyrrole-3-methanol；tert-butyl 3-(hydroxymethyl)pyrrole-1-carboxylate
• CAS: 175689-35-7
• 化学式: C₁₀H₁₅NO₃
• 分子量: 197.234
• InChiKey: CXPNFRZAOUNPJV-UHFFFAOYSA-N

物化性质

• 沸点：
  309.6±34.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(1,1-dimethylethoxycarbonyl)-3-(hydroxymethyl)pyrrole 在 4-乙酰氨基苯磺酰叠氮 、 sodium acetate 、 三乙胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 7.5h， 生成 <1-(1,1-dimethylethoxycarbonyl)-3-pyrrolyl>methyl 2-diazo-3-<(1,1-dimethylethyl)dimethylsiloxy>-3-butenoate
  参考文献：
  名称：

  Divergent Pathways in the Intramolecular Reactions between Rhodium-Stabilized Vinylcarbenoids and Pyrroles:  Construction of Fused Tropanes and 7-Azabicyclo[4.2.0]octadienes

  摘要：

  The rhodium(II)-catalyzed intramolecular reaction between vinyldiazomethanes and pyrroles leads to a novel synthesis of fused tropanes. The reaction occurs by a stepwise 3 + 4 annulation mechanism between a rhodium-stabilized vinylcarbenoid intermediate and the pyrrole rather than by the typical tandem cyclopropanation/Cope rearrangement sequence. The outcome of the reaction is very sensitive to the vinylcarbenoid structure. In particular, the presence of a 2-siloxy substituent on the vinylcarbenoid strongly favors the formation of fused tropanes. In the absence of such functionality, the formation of fused 7-azabicyclo[4.2.0]octadienes becomes the dominant reaction pathway.

  DOI：

  10.1021/jo952127q
• 作为产物：
  描述：

  吡咯-3-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 25.0h， 生成 1-(1,1-dimethylethoxycarbonyl)-3-(hydroxymethyl)pyrrole
  参考文献：
  名称：

  Divergent Pathways in the Intramolecular Reactions between Rhodium-Stabilized Vinylcarbenoids and Pyrroles:  Construction of Fused Tropanes and 7-Azabicyclo[4.2.0]octadienes

  摘要：

  The rhodium(II)-catalyzed intramolecular reaction between vinyldiazomethanes and pyrroles leads to a novel synthesis of fused tropanes. The reaction occurs by a stepwise 3 + 4 annulation mechanism between a rhodium-stabilized vinylcarbenoid intermediate and the pyrrole rather than by the typical tandem cyclopropanation/Cope rearrangement sequence. The outcome of the reaction is very sensitive to the vinylcarbenoid structure. In particular, the presence of a 2-siloxy substituent on the vinylcarbenoid strongly favors the formation of fused tropanes. In the absence of such functionality, the formation of fused 7-azabicyclo[4.2.0]octadienes becomes the dominant reaction pathway.

  DOI：

  10.1021/jo952127q

文献信息

• [EN] BIFUNCTIONAL HETEROCYCLIC COMPOUNDS AND METHODS OF MAKING AND USING THE SAME<br/>[FR] COMPOSES HETEROCYCLIQUES BIFONCTIONNELS ET LEURS PROCEDES D'OBTENTION ET D'UTILISATION
  申请人：RIB X PHARMACEUTICALS INC

  公开号：WO2004078770A1

  公开（公告）日：2004-09-16

  The invention provides a family of bifunctional heterocyclic compounds useful as anti­infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional heterocyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

  这项发明提供了一类双功能杂环化合物家族，可用作抗感染、抗增殖、抗炎和促动力剂。该发明还提供了制备这些双功能杂环化合物的方法，以及将这些化合物用作抗感染、抗增殖剂、抗炎和/或促动力剂的方法。
• Bifunctional heterocyclic compounds and methods of making and using same
  申请人：Wang Deping

  公开号：US20080119419A1

  公开（公告）日：2008-05-22

  The invention provides a family of bifunctional heterocyclic compounds useful as anti-infective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional heterocyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.

  本发明提供了一系列双功能杂环化合物，可作为抗感染、抗增殖、抗炎和促动力药物使用。本发明还提供了制备双功能杂环化合物的方法，以及使用这些化合物作为抗感染、抗增殖剂、抗炎剂和/或促动力剂的方法。
• 10.1039/d4cc01437e
  作者：Shi, Lin、Liu, Lidong、Lei, Xingyu、Wang, Yihan、Fang, Yeguang、Jiao, Peng

  DOI：10.1039/d4cc01437e

  日期：——

  Dearomative 1,3-dipolar cycloadditions of 1-Boc-pyrroles with in situ generated silver α-bromo alkylidenenitronates delivered a series of 3a,6a-dihydro-4-Boc-pyrrolo[2,3-d]isoxazole-2-oxides (17–91% yields) under very mild conditions. N-Deoxygenation of the cycloaddition product gave a dihydro-pyrrolo[2,3-d]isoxazole, elaborations of which produced various functionalized 2,3-dihydropyrroles and pyrrolidines

  1-Boc-吡咯与原位生成的 α-溴亚烷基亚硝基银的脱芳香 1,3-偶极环加成反应生成一系列 3 a ,6 a -二氢-4-Boc-吡咯并[2,3- d ]异恶唑-2-在非常温和的条件下生成氧化物（17-91% 产率）。环加成产物的N-脱氧得到二氢-吡咯并[2,3 -d ]异恶唑，其精加工产生各种官能化的2,3-二氢吡咯和吡咯烷，展示了我们的吡咯脱芳构化新策略的潜在效用。
• Bifunctional heterocyclic compounds and methods of making and using the same
  申请人：Farmer J. Jay

  公开号：US20070072811A1

  公开（公告）日：2007-03-29

  The invention provides a family of bifunctional heterocyclic compounds useful as antiinfective, anti-proliferative, anti-inflammatory, and prokinetic agents. The invention also provides methods of making the bifunctional heterocyclic compounds, and methods of using such compounds as anti-infective, anti-proliferative agents, anti-inflammatory, and/or prokinetic agents.
• US6828427B1
  申请人：——

  公开号：US6828427B1

  公开（公告）日：2004-12-07