2-(phenylethynyl)cyclopentanecarboxylic acid | 148028-96-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(phenylethynyl)cyclopentanecarboxylic acid
• 英文别名: 2-(phenylethynyl)-cyclopent-1-ene-1-carboxylic acid；2-phenylethynylcyclopentene-1-carboxylic acid；2-(2-phenylethynyl)cyclopentene-1-carboxylic acid
• CAS: 148028-96-0
• 化学式: C₁₄H₁₂O₂
• 分子量: 212.248
• InChiKey: ZWWOPBNLSMWHBW-UHFFFAOYSA-N

物化性质

• 沸点：
  362.6±42.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(phenylethynyl)cyclopentanecarboxylic acid 在 氯化铵 、 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 1,4-二氧六环 为溶剂， 反应 20.0h， 以87%的产率得到2-(phenylethynyl)cyclopent-1-ene-1-carboxamide
  参考文献：
  名称：

  烯炔酰胺到稠合吡啶酮：范围和限制

  摘要：

  在此，我们对从相应的烯炔酰胺合成环戊基和杂环稠合吡啶酮的范围和机制进行了研究。在仲胺的存在下，环化顺利进行，以 12-90% 的产率形成 5,6-双环吡啶酮。六元和更大环系统的烯炔酰胺环化失败。闭环反应对于仲胺而言本质上是催化性的，并且通过胺的顺序1,6-加成、亚胺中间体的6-外-三环闭环以及随后的仲胺的消除进行。计算表明，对于六元和更大的系统，烯炔和酰胺之间的共轭减少，从而为此类烯炔酰胺无法形成稠合吡啶酮提供了解释。

  DOI：

  10.1021/acs.joc.1c00688
• 作为产物：
  描述：

  2-(三氟甲基磺酰氧基)-1-环戊烯-1-甲酸乙酯 在 2,6-二甲基吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium hydroxide 、 copper(l) iodide 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(phenylethynyl)cyclopentanecarboxylic acid
  参考文献：
  名称：

  Nakatani; Maekawa; Tanabe, Journal of the American Chemical Society, 1995, vol. 117, # 43, p. 10635 - 10644

  摘要：

  DOI：

文献信息

• Regio- and Stereoselective Synthesis of Cyclic Imidates via Electrophilic Cyclization of 2-(1-Alkynyl)benzamides. A Correction
  作者：Saurabh Mehta、Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo301958q

  日期：2012.12.7

  The electrophilic cyclization of 2-(1-alkynyl)benzamides affords high yields of cyclic imidates, instead of the previously reported isoindolin-1-ones, where cyclization proceeds on the oxygen of the carbonyl group rather than the nitrogen of the amide functionality. X-ray crystallography and spectroscopic techniques have been used to characterize the products. A correction is hereby provided in order

  2-(1-炔基)苯甲酰胺的亲电环化提供了高产率的环状亚胺酸酯，而不是先前报道的异吲哚啉-1-酮，其中环化在羰基的氧而不是酰胺官能团的氮上进行。X 射线晶体学和光谱技术已用于表征产品。特此提供更正以纠正先前的结构错误分配。
• Photoinduced DNA cleavage by designed molecules with conjugated ene-yne-ketene functionalities
  作者：Kazuhiko Nakatani、Sachihiko Isoe、Satoshi Maekawa、Isao Saito

  DOI：10.1016/s0040-4039(00)75850-3

  日期：1994.1

  Upon photoirradiation, diazoketone 1 was found to induce single strand cleavage of plasmid pBR322 DNA at concentration of 100 mu M. Conjugate ene-yne moiety was essential for DNA-cleaving activities.
• Synthesis of 2-(4-carboxybutenyl)- and 2-(4-carboxybutynyl)-cyclopentene-1-carboxamides
  作者：Anne Beauchard、Victoria A. Phillips、Matthew D. Lloyd、Michael D. Threadgill

  DOI：10.1016/j.tet.2009.07.085

  日期：2009.9

  Syntheses of 2-(4-carboxybut-1-enyl/4-carboxypent-1-ynyl)cyclopentene-1-carboxamides, compounds designed to mimic the phosphoSer-Pro dipeptide motif (the recognition sequence for the prolyl cis-trans isomerase Pin1), have been developed. Stille, Sonogashira and Suzuki couplings were envisaged to join the pentynoic and pentenoic acid side chains to the 2-position of cyclopentene-1-carboxylate esters. The ring- and side-chain carboxylic acids required orthogonal protection for later attachment of a Ph-NH(4-nitrophenyl) unit to the cyclopentene-1-carbonyl. The cyclopentenecarboxylates were unmasked and standard PyBOP peptide coupling afforded the target compounds. Comparisons of two routes using Bur and Me esters are reported. (C) 2009 Elsevier Ltd. All rights reserved.
• Regio- and Stereoselective Synthesis of Isoindolin-1-ones via Electrophilic Cyclization
  作者：Tuanli Yao、Richard C. Larock

  DOI：10.1021/jo048007c

  日期：2005.2.1

  A variety of substituted isoindolin-l-ones are readily prepared in good to excellent yields under very mild reaction conditions by the reaction of o-(1-alkynyl)benzamides with ICI, I-2, and NBS. In a few cases, substituted isoquinolin-1-ones were obtained as the major product instead. This methodology accommodates various alkynyl amides and functional groups and has been successfully extended to heterocyclic starting materials. This chemistry has been successfully applied to the synthesis of a biologically interesting alkaloid, cepharanone B.
• Nakatani Kazuhiko, Isoe Sachihiko, Maekawa Satoshi, Saito Isao, Tetrahedron Lett, 35 (1994) N 4, S 605-608
  作者：Nakatani Kazuhiko, Isoe Sachihiko, Maekawa Satoshi, Saito Isao

  DOI：——

  日期：——