2-乙炔基吡咯-1-羧酸,t-丁酯 | 467435-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 2-乙炔基吡咯-1-羧酸,t-丁酯
• 中文别名: 2-乙炔基吡咯-1-甲酸叔丁酯
• 英文名称: 2-ethynylpyrrole-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl 2-ethynyl-1H-pyrrole-1-carboxylate；tert-butyl 2-ethynylpyrrole-1-carboxylate
• CAS: 467435-75-2
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD09753548
• 分子量: 191.23
• InChiKey: BXYGCGZVOKUUCH-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于氯仿（少许）、DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-乙炔基吡咯-1-羧酸,t-丁酯 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 41.0h， 生成 2,7-二-(1H-吡咯-2-基)乙炔基-1,8-萘啶
  参考文献：
  名称：

  Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors:  Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine

  摘要：

  The push-pull conjugated molecules 2,7-bis-(1 H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN) and 2,7-bis(1H-indol-2-yl)ethynyl-1,8-naphthyridine (BIN) adopting daad relays of proton donors (d) and acceptors (a) form multiple hydrogen-bonding complexes with various monosaccharides that possess complementary adda sequences. Although the free BPN emits blue light at lambda(max) = 475 nm in CH2CI2, its complexation with octyl ss-D-glucopyranoside gives green fluorescence at lambda(max) = 535 nm. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM. On the other hand, the CD-silent BIN molecule binds with monosaccharides to form the CD-active multiple hydrogen-bonding complexes, which exhibit the remarkable chirality dependent helicities consistent with the prediction by the ab initio approaches. On the basis of the similar daad cleft and hence the binding property, the fluorescence and CD absorption methods in BPN and BIN, respectively, are complementary, which, in combination with computational molecular modeling, not only give a detailed insight into the structures of the receptor-saccharide complexes in solution, but also differentiate octyl beta-D-glucopyranoside from its enantiomer and other monosaccharides.

  DOI：

  10.1021/ja039237w
• 作为产物：
  描述：

  1-Boc-2-溴-1H-吡咯 在 bis-triphenylphosphine-palladium(II) chloride potassium fluoride 、 copper(l) iodide 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 26.0h， 生成 2-乙炔基吡咯-1-羧酸,t-丁酯
  参考文献：
  名称：

  2,7-Bis(1H-pyrrol-2-yl)ethynyl-1,8naphthyridine:  An Ultrasensitive Fluorescent Probe for Glucopyranoside

  摘要：

  [GRAPHICS]A push-pull conjugated molecule, 2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN), has been designed to bind selectively with octyl glucopyranoside (OGU). The BPN/OGU quadruple hydrogen-bonding complex adopts a rigid BPN conformation in which the proton donor (d) and acceptor (a) relays (daad) are resonantly conjugated through the ethynyl bridge, inducing pi-electron delocalization, i.e., a charge transfer effect. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM.

  DOI：

  10.1021/ol0264096

文献信息

• Iron-Catalyzed Alkylzincation of Terminal Alkynes
  作者：Qiang Huang、Wei-Na Wang、Shou-Fei Zhu

  DOI：10.1021/acscatal.1c05870

  日期：2022.2.18

  Although carbozincation of terminal alkynes is a promising method for the synthesis of alkenylzinc reagents, many challenges, especially the chemo-, regio-, and stereoselectivity, remain to be addressed. Herein we report an operationally simple, mild method for iron-catalyzed alkylzincation of terminal alkynes to produce a diverse array of alkenylzinc compounds in high yields with high anti-Markovnikov

  尽管末端炔烃的羰基化是合成烯基锌试剂的一种很有前途的方法，但仍有许多挑战，特别是化学选择性、区域选择性和立体选择性有待解决。在这里，我们报告了一种操作简单、温和的方法，用于铁催化末端炔烃的烷基锌化，以高产率、高反马尔科夫尼科夫选择性和高顺式立体选择性产生多种烯基锌化合物。使用该方法，我们实现了末端炔烃的顺式烷基锌化，证明该方法具有广泛的底物范围（适用于芳基、烯基、烷基和杂原子取代的乙炔）和良好的官能团耐受性。因为 C(sp 2)─产物的锌键可以很容易地转化，该方法为传统的三取代烯烃选择性合成方法提供了具有竞争力的替代方案。本研究开发的铁催化剂在炔烃烷基化中表现出不可替代的反应性
• Ethynyl-Linked (Pyreno)pyrrole−Naphthyridine and Aniline−Naphthyridine Molecules as Fluorescent Sensors of Guanine via Multiple Hydrogen Bondings
  作者：Shao-Hung Lu、Srinivasan Selvi、Jim-Min Fang

  DOI：10.1021/jo061831b

  日期：2007.1.1

  [GRAPHICS]New fluorescent molecular sensors for 9-alkylguanines were constructed by conjugation of 2-acetamido-1,8-naphthyridine with N-Boc-pyrrole, N-Boc-pyreno[2,1-b]pyrrole, or acetanilide moieties via an ethynyl bridge. In combination with the triple hydrogen-bonding motif of 2-acetamidonaphthyridine toward alkylguanine, an additional binding site was provided by the substituent properly located on the pyrrole or aniline ring to enhance the affinity of these receptor molecules. Besides the ESI-MS analyses, the binding events were readily monitored by the absorption and fluorescence changes in the visible region.
• A Pyrrolyl-Based Triazolophane: A Macrocyclic Receptor With CH and NH Donor Groups That Exhibits a Preference for Pyrophosphate Anions
  作者：Jonathan L. Sessler、Jiajia Cai、Han-Yuan Gong、Xiaoping Yang、Jonathan F. Arambula、Benjamin P. Hay

  DOI：10.1021/ja107098r

  日期：2010.10.13

  A pyrrolyl-based triazolophane, incorporating CH and NH donor groups, acts as a receptor for the pyrophosphate anion in chloroform solution. It shows selectivity for this trianion, followed by HSO4- > H2PO4- > Cl- > Br- (all as the corresponding tetrabutylammonium salts), with NH-anion interactions being more important than CH-anion interactions. In the solid state, the receptor binds the pyrophosphate anion in a clip-like slot via NH and CH hydrogen bonds.
• 2,7-Bis(1<i>H</i>-pyrrol-2-yl)ethynyl-1,8naphthyridine:  An Ultrasensitive Fluorescent Probe for Glucopyranoside
  作者：Jen-Hai Liao、Chao-Tsen Chen、He-Chun Chou、Chung-Chih Cheng、Pi-Tai Chou、Jim-Min Fang、Zdenek Slanina、Tashin J. Chow

  DOI：10.1021/ol0264096

  日期：2002.9.1

  [GRAPHICS]A push-pull conjugated molecule, 2,7-bis(1H-pyrrol-2-yl)ethynyl-1,8-naphthyridine (BPN), has been designed to bind selectively with octyl glucopyranoside (OGU). The BPN/OGU quadruple hydrogen-bonding complex adopts a rigid BPN conformation in which the proton donor (d) and acceptor (a) relays (daad) are resonantly conjugated through the ethynyl bridge, inducing pi-electron delocalization, i.e., a charge transfer effect. The excellent photophysical properties make BPN a highly sensitive probe for monitoring glucopyranoside to a detection limit of similar to100 pM.
• [EN] 1-(2-(4-CYCLOPROPYL-1H-1,2,3-TRIAZOL-1-YL)ACETYL)-4-HYDROXYPYRROLIDINE-2-CARBOXA|MIDE DERIVATIVES AS VHL INHIBITORS FOR THE TREATMENT OF ANEMIA<br/>[FR] DÉRIVÉS DE 1-(2-(4-CYCLOPROPYL-1H-1,2,3-TRIAZOL-1-YL)ACÉTYL)-4-HYDROXYPYRROLIDINE-2-CARBOXAMIDE SERVANT D'INHIBITEURS DE VHL POUR LE TRAITEMENT DE L'ANÉMIE
  申请人：[en]GENENTECH, INC.

  公开号：WO2022104345A1

  公开（公告）日：2022-05-19

  The present disclosure relates to l-(2-(4-cyclopropyl-lH-l,2,3- triazol-l-yl)acetyl)-4-hydroxypyrrolidine-2-carboxamide derivatives and structurally related compounds of formula (I) as VHL inhibitors for the treatment of e.g. anemia (e.g. chronic anemia or anemia associated with chronic kidney disease, dialysis or cancer chemotherapy), ischemia, stroke or damage to the cardiovascular system during ischemia, or for enhancing wound healing, reducing scarring, or enhancing angiogenesis or arteriogenesis. Exemplary compounds are e.g.: • 1 -(2-(4-cyclopropyl- lH-l,2,3-triazol-l -yl)-3,3-dimethylbutanoyl)-4- hydroxypyrrolidine-2-carboxamide; • 1 -(2-(4-cyclopropyl- 1H-1,2,3 -triazol-1 -yl)-3,3 -dimethylbutanoyl) -4-hydroxy-N-methylpyrrolidine-2-carboxamide; • 1 -(2-cyclohexyl-2-(4-cyclopropyl- lH-l,2,3-triazol-l -yl)acetyl)-4- hydroxy-N-methylpyrrolidine-2-carboxamide; • 1 -(3,3 -dimethyl-2-( lH-l,2,3-triazol-l -yl)butanoyl)-4-hydroxy-N- methylpyrrolidine-2-carboxamide; • l-(2-( 4-cyclopropyl-lH-l,2,3-triazol-l-yl)-2-(l-methylcyclohexyl) acetyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide; • l-(2-( 4-cyclopropyl-lH-l,2,3-triazol-l-yl)-2-(tetrahydro-2H-pyran-4- yl)acetyl)-4-hydroxy-N-methylpyrrolidine-2-carboxamide.