2-carbethoxy-3-hydroxypyrrole | 65171-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-carbethoxy-3-hydroxypyrrole
• 英文别名: Ethyl-3-hydroxypyrrol-2-carboxylat；3-Hydroxy-pyrrole-2-carboxylic acid ethyl ester；ethyl 3-hydroxypyrrole-2-carboxylate；Ethyl 3-hydroxy-1H-pyrrole-2-carboxylate
• CAS: 65171-89-3
• 化学式: C₇H₉NO₃
• 分子量: 155.153
• InChiKey: KHQHIVHXOLYMDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  62.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-carbethoxy-3-hydroxypyrrole 以 乙腈 为溶剂， 反应 48.0h， 生成 3,3'-Dioxo-1,3,1',3'-tetrahydro-[2,2']bipyrrolyl-2,2'-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  光诱导的3-羟基吡咯脱氢二聚

  摘要：

  在CH 3 CN中辐射3-羟基-1 H-吡咯-2-羧酸酯1（λ> 280 nm）得到[2.2'-bi（3-oxo-2,3-dihydro-1 H-吡咯）]- 2-，2′-二羧酸酯2以合理的到良好的产率。相应的N-甲基吡咯3仅在相似条件下经历缓慢的光分解。合成了几种2-甲基-3-氧代-2,3-二氢-1 H-吡咯-2-羧酸酯4和5，以将其光谱数据与脱氢二聚体2的光谱数据进行比较。对二乙基[2,2'-bi（4,5-二甲基-3-氧代-2,3-二氢-1 H]进行了X射线结构分析-吡咯）]-2，2′-二羧酸酯（2b）。最初提出的化合物2a - e的[3,3'-bi（3 H-吡咯）]结构证明是错误的。

  DOI：

  10.1002/hlca.19840670734
• 作为产物：
  描述：

  ethyl [(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidenemethyl)amino]acetate 200.0~600.0 ℃ 、5.07 Pa 条件下， 以85%的产率得到2-carbethoxy-3-hydroxypyrrole
  参考文献：
  名称：

  N-未取代的3-羟基吡咯和1H-吡咯-3（2H）-一的气相合成

  摘要：

  闪蒸真空热解（FVP）在600˚C的Meldrum酸的甲基氨基亚甲基衍生物在甲基上带有吸电子取代基，提供N-未取代的3-羟基吡咯和/或1 H -pyrrol-3（2 H）-高让。 气相反应-周环反应-杂环-吡咯-区域选择性

  DOI：

  10.1055/s-0029-1217397

文献信息

• Method for the synthesis of pyrrole and imidazole carboxamides on a
  申请人：California Institute of Technology

  公开号：US06090947A1

  公开（公告）日：2000-07-18

  The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.

  本发明描述了一种新颖的固相合成聚酰胺的方法，其中聚酰胺含有咪唑和吡咯羧酰胺。这些聚酰胺是通过芳香羧酸和芳香胺在固体支持上制备的，具有高步骤偶联产率（>99%），提供毫克级高纯度聚酰胺。本发明还描述了合成天然产物Netropsin和Distamycin A的类似物的方法，这两种是抗病毒抗生素。本发明还描述了一种新颖的固相合成咪唑和吡咯羧酰胺聚酰胺-寡核苷酸结合物的方法。这种方法将大大增加可以合成和测试的小沟结合聚酰胺和小沟结合聚酰胺-寡核苷酸结合物的复杂性和数量。
• Ozonolysis of 2-(1,4-cyclohexadienyl)glycine
  作者：Gury Zvilichovsky、Vadim Gurvich

  DOI：10.1016/0040-4020(95)00209-q

  日期：1995.5

  Derivatives of 2-(1,4-cyclohexadienyl)glycine were subjected to total ozonolysis. The free esters as well as the N-protected esters tend to cyclize to yield 2-carbethoxy-3-hydroxy pyrrole derivatives. By treatment of the ozonolysis mixture with hydroxylamine or phenylhydrazine heterocyclic derivatives of glycine were obtained. The structure and formation of pyrazolyl and isoxazolyl glycine derivatives

  对2-（1,4-环己二烯基）甘氨酸的衍生物进行整体臭氧分解。游离酯和N-保护的酯倾向于环化以产生2-碳乙氧基-3-羟基吡咯衍生物。通过用羟胺或苯肼处理该臭氧分解混合物，获得了甘氨酸的杂环衍生物。讨论了吡唑基和异恶唑基甘氨酸衍生物的结构和形成。通过X射线单晶分析报道了N-乙酰基-2-（1-苯基吡唑-3-基）甘氨酸乙酯的结构。
• Photochemistry of 2-Allyl-3-oxo-2,3-dihydro-1H-pyrrole-2-carboxyalates
  作者：Michael Beyer、Ramin Ghaffari-Tabrizi、Michael Jung、Paul Margaretha

  DOI：10.1002/hlca.19840670618

  日期：1984.9.26

  On acetone-sensitized irradiation the title compounds 3a–c are converted to 2-allyl-3-hydroxy-1H-pyrrole-2-carboxylates 4 in reasonable yields.

  在丙酮敏化辐射下，标题化合物3a–c以合理的产率转化为2-烯丙基-3-羟基-1 H-吡咯-2-羧酸酯4。
• Light-induced dehydrodimerization of pyrroles. Preliminary communication
  作者：Ramin Ghaffari-Tabrizi、Paul Margaretha

  DOI：10.1002/hlca.19830660631

  日期：1983.9.21

  Irradiation (λ>280 nm) of 3-hydroxypyrroles 1 in acetonitrile leads to the formation of 3,3′-bi-3H-pyrroles 2 in reasonable to good yields.

  在乙腈中辐照（λ> 280 nm）3-羟基吡咯1导致以合理至良好的产率形成3,3'-bi-3 H-吡咯2。
• 2,2'-bi-1H-pyrrole derivatives with immunosuppressant activity
  申请人：Pharmacia Italia S.p.A.

  公开号：EP1241162A1

  公开（公告）日：2002-09-18

  New and known 5-[(2H-pyrrol-2-ylidene)methyl]-2,2'-bi-1H-pyrrole derivatives, having immunomodulating activity and, represented by the following general formula (I) wherein, subject to a proviso, R1 represents hydrogen, phenyl, C1-C20 alkyl or C2-C20 alkenyl, wherein the alkyl and alkenyl groups may be unsubstituted or substituted by 1 to 3 substituents chosen independently from halogen, C1-C6 alkoxy, hydroxy, aryl and aryloxy; R2 represents hydrogen, C1-C6 alkyl, cyano, carboxy or (C1-C6 alkoxy) carbonyl; R3 represents halogen, hydroxy or C1-C11 alkoxy unsubstituted or substituted by phenyl; R4 represent hydrogen, C1-C6 alkyl or phenyl; each or R5 and R6 independently represents hydrogen, C2-C20 alkanoyl, C3-C20 alkenoyl, phenyl, C1-C20 alkyl or C2-C20 alkenyl, wherein the alkanoyl, alkenoyl, alkyl and the alkenyl groups may be unsubstituted or substituted by 1 to 3 substituents chosen independently from halogen, C1-C6 alkoxy, hydroxy, aryl, aryloxy, cyano, carboxy, (C1-C6 alkoxy)carbonyl, (C3-C4 alkenyl)carbamoyl, aralkylcarbamoyl, arylcarbamoyl and -CONRcRd in which each of Rc and Rd independently is hydrogen or C1-C6 alkyl or Rc arid Rd, taken together with the nitrogen atom to which they are linked, form a morpholino or piperidino ring; or two of R4, R5 and R6 taken together form a C4-C12 polymethylene chain, which can be unsubstituted or substituted by a C1-C12 alkyl, by a C2-C12 alkenyl or by a C1-C12 alkylidene group, wherein the alkyl, alkenyl and alkylidene groups may be in turn unsubstituted or substituted by a substituent chosen from halogen, C1-C6 alkoxy, hydroxy, cyano, carboxy, (C1-C6 alkoxy)carbonyl, aryloxy and aryl; the remaining one being hydrogen or C1-C12 alkyl; and the pharmaceutically acceptable salts thereof, are disclosed.

  具有免疫调节活性的新的和已知的 5-[(2H-吡咯-2-亚基)甲基]-2,2'-双-1H-吡咯衍生物，由以下通式(I)表示 其中，根据但书，R1 代表氢、苯基、C1-C20 烷基或 C2-C20 烯基，其中烷基和烯基可以未被取代或被 1 至 3 个独立选自卤素、C1-C6 烷氧基、羟基、芳基和芳氧基的取代基取代；R2 代表氢、C1-C6 烷基、氰基、羧基或（C1-C6 烷氧基）羰基；R3 代表卤素、羟基或未被取代或被苯基取代的 C1-C11 烷氧基；R4 代表氢、C1-C6 烷基或苯基；其中每个 Rc 和 Rd 独立地为氢或 C1-C6 烷基，或 Rc 和 Rd 与它们连接的氮原子一起形成吗啉环或哌啶环；或 R4、R5 和 R6 中的两个共同形成 C4-C12 聚亚甲基链，该链可以未被 C1-C12 烷基、C2-C12 烯基或 C1-C12 亚烷基取代，其中烷基、烯基和亚烷基可依次未被取代或被选自卤素、C1-C6 烷氧基、羟基、氰基、羧基、(C1-C6 烷氧基)羰基、芳氧基和芳基的取代基取代；余下的一个为氢或 C1-C12 烷基；及其药学上可接受的盐，均已公开。