(2-甲酰基-1H-吡咯-1-基)乙酸 | 67451-42-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: (2-甲酰基-1H-吡咯-1-基)乙酸
• 英文名称: 2-(2-formyl-1H-pyrrol-1-yl)acetic acid
• 英文别名: (2-formyl-1-pyrryl)acetic acid；(2-formyl-1H-pyrrol-1-yl)acetic acid；2-(2-formylpyrrol-1-yl)acetic acid
• CAS: 67451-42-7
• 化学式: C₇H₇NO₃
• mdl: MFCD08752783
• 分子量: 153.137
• InChiKey: VQNKRZLHJSBDGY-UHFFFAOYSA-N

物化性质

• 熔点：
  140-141 °C(Solv: water (7732-18-5))
• 沸点：
  358.4±22.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  59.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  (2-甲酰基-1H-吡咯-1-基)乙酸 在 ammonium acetate 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以67%的产率得到[2-(氨基甲基)-1H-吡咯-1-基]乙酸
  参考文献：
  名称：

  1,2-二取代吡咯的合成：顺式肽键替代

  摘要：

  据报道，通过NaCNBH 3的还原胺化1可以简单而通用地合成1,2-二取代的吡咯2。Gly-ψ[C 4 N] -X二肽2是顺式二肽3的替代物。

  DOI：

  10.1016/0040-4039(92)89043-c
• 作为产物：
  描述：

  ethyl 2-(2-formyl-1H-pyrrol-1-yl)acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 生成 (2-甲酰基-1H-吡咯-1-基)乙酸
  参考文献：
  名称：

  New Melanoidin-like Maillard Polymers from 2-Deoxypentoses

  摘要：

  In the 2-deoxy-D-ribose/methyl 4-aminobutyrate Maillard system a trapped N-substituted 2-(hydroxymethyl)pyrrole is one of the major products. However, nontrapped representatives of this type of compound were hitherto not found in other Maillard model systems, indicating their extraordinary reactivity. Model experiments with 2-deoxy-D-ribose/methylamine enabled the detection of N-methyl-2-(hydroxymethyl)pyrrole (1) and some derived linear oligomers (2, 3) as minor components. Consequently, 1 was synthesized and its oligomerization studied under very mild acidic conditions. The deformylated dimeric bis(N-methyl-2-pyrrolyl)methane (2) and trimeric N-methyl-2,5-bis(N-methyl-2-pyrrolylmethyl)pyrrole (3) were characterized by GC/MS and NMR. Higher regular oligomers up to 6 N-methyl-2-pyrrolylmethyl units as well as corresponding dehydro-oligomers up to 12 units were identified by MALDI-TOF-MS. A complementary experiment starting with N-methyl-2-hydroxy[C-13]methylpyrrole ([(CH2OH)-C-13]-1) confirmed the structure and the oligomerization pathway. The possible significance of this type of model oligomer for the melanoidin formation in Maillard reactions is discussed. The antioxidative activity of the isolated dimer and trimer was tested in Fe(III)-thiocyanate and DPPH assays.

  DOI：

  10.1021/jf970657c

文献信息

• Improved functionalized resin for chemical synthesis
  申请人：PFIZER INC.

  公开号：EP0801083A3

  公开（公告）日：1999-12-29

  A support functionalized by an indole or pyrrole aldehyde is useful for the solid phase synthesis of amide type compounds.

  通过吲哚或吡咯醛基团功能化的支持体对酰胺类化合物的固相合成是有用的。
• Diastereoselective Ugi reaction without chiral amines: the synthesis of chiral pyrroloketopiperazines
  作者：Valentine G. Nenajdenko、Alexander L. Reznichenko、Elizabeth S. Balenkova

  DOI：10.1016/j.tet.2007.01.056

  日期：2007.4

  The three-component Ugi reaction with chiral 2-(2-formyl-1H-pyrrol-1-yl)acetic acids prepared from natural l-aminoacids was investigated. The reaction opens a new route to chiral substituted pyrroloketopiperazines. One of the first examples of an asymmetric Ugi reaction without chiral amines is described. The reaction proceeds with moderate diastereoselectivity to give the target compounds in good

  研究了由天然1-氨基酸制得的手性2-（2-甲酰基-1 H-吡咯-1-基）乙酸与三组分Ugi反应。该反应为手性取代的吡咯并酮哌嗪开辟了一条新途径。描述了没有手性胺的不对称Ugi反应的第一个例子。反应以适度的非对映选择性进行，以高收率得到目标化合物。讨论了该方法的范围和局限性。
• Divergent, C–C Bond Forming Macrocyclizations Using Modular Sulfonylhydrazone and Derived Substrates
  作者：Wenqing Xu、Lauren E. Brown、John A. Porco

  DOI：10.1021/acs.joc.1c01848

  日期：2021.12.3

  forming macrocycle construction is described. Modular sulfonylhydrazone and derived pyridotriazole substrates with three key building blocks have been constructed and cyclized to afford diverse macrocyclic frameworks. Broad substrate scope and functional group tolerance have been demonstrated. In addition, site-selective postfunctionalization allowed for further diversification of macrocyclic cores.

  描述了形成 C-C 键的大环结构的不同方法。具有三个关键结构单元的模块化磺酰腙和衍生的吡啶并三唑底物已被构建并环化以提供不同的大环框架。广泛的底物范围和官能团耐受性已被证明。此外，位点选择性后官能化允许大环核的进一步多样化。
• Cephalosporin derivatives
  申请人：Yeda Research and Development Co., Ltd.

  公开号：US04122260A1

  公开（公告）日：1978-10-24

  New cephalosporin derivatives containing a formyl substituted pyrrole group and the processes for preparing same are described.

  描述了含有甲酰基取代吡咯基团的新头孢菌素衍生物以及其制备过程。
• FORMYLPYRROLE-BASED HETEROCYCLES FOR NUCLEIC ACID ATTACHMENT TO SUPPORTS
  申请人：IIIumina, Inc.

  公开号：US20150031833A1

  公开（公告）日：2015-01-29

  A compound has Formula I: A, B, C, D, W, X, Y, and Z are independently selected from hydrogen, optionally substituted C 1 -C 6 alkyl, optionally substituted C 1 -C 6 alkoxy, aryl, aldehyde, protected aldehyde, CH, N, O, S, null, and bond; Q is selected from aldehyde, protected aldehyde, and null, at least one of A, B, C, D, W, X, Y, Z, or Q is an aldehyde or protected aldehyde; the bonds between each of A-B, B-C, C-D, W-X, X-Y, and Y-Z are selected from single bond, double bond, triple bond, and no bond; L is a linker selected from a C 1 -C 12 alkyl, aralkyl, and aryl, any of which is optionally substituted; one or more methylene unit (CH 2 ) of the C 1 -C 12 alkyl is optionally replaced by any combination of oxygen, carbonyl(C═O), and NH; and R 1 and R 2 are independently selected from —NR 3 R 4 , halogen, C 1 -C 8 alkoxy, aralkoxy, alkenyloxy, alkynyloxy, and OCH 2 CH 2 CN; R 3 and R 4 are independently a C 1 -C 4 , straight chain or branched alkyl group.

  化合物的化学式为I：A，B，C，D，W，X，Y和Z分别从氢，可选取代的C1-C6烷基，可选取代的C1-C6烷氧基，芳基，醛，保护醛，CH，N，O，S，空和键中独立选择；Q从醛，保护醛和空中选择，A，B，C，D，W，X，Y，Z或Q中至少有一个是醛或保护醛；A-B，B-C，C-D，W-X，X-Y和Y-Z之间的键从单键，双键，三键和无键中选择；L是从C1-C12烷基，芳基烷基和芳基中选择的连接物，其中任何一个都可以被选择性地取代；C1-C12烷基的一个或多个亚甲基（CH2）可以被任何氧，羰基（C═O）和NH的任意组合替换；R1和R2分别从—NR3R4，卤素，C1-C8烷氧基，芳基烷氧基，烯基氧基，炔基氧基和OCH2CH2CN中独立选择；R3和R4分别是C1-C4直链或支链烷基。