4-(carboxymethyl)cyclopent-2-en-1-one methyl ester | 51388-62-6

• 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
• 英文名称: 4-(carboxymethyl)cyclopent-2-en-1-one methyl ester
• 英文别名: 4-Oxo-cyclopenten-(2)-essigsaeure-methylester-(1)；<4-Oxo-cyclopent-2-en-yl>-essigsaeure-methylester；methyl (4-oxocyclopent-2-en-1-yl)acetate；methyl 2-(4-oxocyclopent-2-en-1-yl)acetate
• CAS: 51388-62-6
• 化学式: C₈H₁₀O₃
• 分子量: 154.166
• InChiKey: UHBQSMPWZRDQAD-UHFFFAOYSA-N

物化性质

• 沸点：
  238.6±19.0 °C(Predicted)
• 密度：
  1.132±0.06 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：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(carboxymethyl)cyclopent-2-en-1-one methyl ester 在 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 copper(l) iodide 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 ((1S,2S)-4-Oxo-2-vinyl-cyclopentyl)-acetic acid methyl ester
  参考文献：
  名称：

  Cheng, Peter T. W.; McLean, Stewart, Canadian Journal of Chemistry, 1989, vol. 67, p. 261 - 267

  摘要：

  DOI：
• 作为产物：
  描述：

  5-降冰片烯-2-醇 在 sodium hydroxide 、 重铬酸吡啶 、 jones reagent 、 双氧水 、 三氟乙酸吡啶 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 6.67h， 生成 4-(carboxymethyl)cyclopent-2-en-1-one methyl ester
  参考文献：
  名称：

  A new, elegant route to a key intermediate for the synthesis of 9(0)-methanoprostacyclin

  摘要：

  DOI：

  10.1021/jo01311a047

文献信息

• Synthetic Photochemistry. XIII. Chiroptical Retention for the Reported “<i>antara-antara</i>”-3,3-Sigmatropy of Bicyclo[3.2.0]hepta-3,6-dien-2-ones
  作者：Hitoshi Takeshita、Masatoshi Kumamoto、Isao Kouno

  DOI：10.1246/bcsj.53.1006

  日期：1980.4

  Troponoids were shown to form 2:1-complexes with β-cyclodextrin and 1:1-complexes with α-cyclodextrin. The photoisomerization of complexed tropolone and 2-methoxytropone gave optically active 1-hydroxy- and 1-methoxybicyclo[3.2.0]hepta-3,6-dien-2-ones in improved yields. The pyrolysis of the (+)-1-methoxybicyclo[3.2.0]hepta-3,6-dien-2-one gave the (+)-3-methoxybicyclo[3.2.0]hepta-3,6-dien-2-one, ruling

  肌钙蛋白与 β-环糊精形成 2:1-复合物，与 α-环糊精形成 1:1-复合物。络合的托酚酮和 2-甲氧基托酮的光异构化以提高的产率得到光学活性的 1-羟基-和 1-甲氧基双环 [3.2.0]hepta-3,6-dien-2-ones。(+)-1-甲氧基双环[3.2.0]hepta-3,6-dien-2-one热解得到(+)-3-甲氧基双环[3.2.0]hepta-3,6-dien-2 - 一，排除了双重 supra-antara-1,3-sigmatropy。
• Total Syntheses of Two Self-polymerizable Carbocyclic Analogues of 2?-deoxyribonucleosides
  作者：Jianji Wang、Albert Gossauer

  DOI：10.1002/hlca.19940770214

  日期：1994.3.23

  A short regio- and stereoselective synthesis of two carbocyclic 3′-deoxynucleoside analogues is described, the key step of which consists in the photosensitized addition of MeOH to a cyclopent-2-enone derivative. As in both cases functional groups capable to react with each other are present in the same molecule, the synthetic compounds can form polymers similar to oligonucleotides.

  描述了两个碳环3'-脱氧核苷类似物的短区域和立体选择性合成，其关键步骤在于将MeOH光敏加成到环戊-2-烯酮衍生物中。由于在两种情况下，能够相互反应的官能团都存在于同一分子中，所以合成的化合物可以形成类似于寡核苷酸的聚合物。
• Enantioselective Photoreaction of 4-Isopropyltropolone Methyl Ether in Inclusion Crystals with Optically Active Host Compounds
  作者：Koichi Tanaka、Ryoji Nagahiro、Zofia Urbanczyk-Lipkowska

  DOI：10.1021/ol015857v

  日期：2001.5.1

  Upon photoirradiation of a 2:1:1 inclusion complex of (−)-1, 4-isopropyltropolone methyl ether (3b) and chroloform, optically active photocyclization products (−)-6a and (−)-7a were obtained in 96% and 90% ee, respectively.

  在 (-)-1, 4-异丙基托酚酮甲醚 (3b) 和三氯甲烷的 2:1:1 包合物的光照射下，获得 96% 的光学活性光环化产物 (-)-6a 和 (-)-7a，分别为 90% ee。
• Enhancing Flavins Photochemical Activity in Hydrogen Atom Abstraction and Triplet Sensitization through Ring‐Contraction
  作者：Andreas Rehpenn、Stephan Hindelang、Khai‐Nghi Truong、Alexander Pöthig、Golo Storch

  DOI：10.1002/anie.202318590

  日期：2024.4.15

  ring-contracted imidazolonequinoxalines with increased triplet energy (ET) and H-atom abstraction (HAT) strength in the photochemically excited state. Ring-contracted flavins are efficient catalysts in the trifluoromethylthiolation of aliphatic C−H positions and also in multi-step sequences, which require the combined activity as triplet sensitizer and hydrogen atom abstractor.

  酯改性黄素与氢氧化物碱的反应产生环收缩的咪唑啉酮喹喔啉，其在光化学激发态下具有增加的三线态能量（ ET ）和氢原子夺取（HAT）强度。缩环黄素是脂肪族 C-H 位三氟甲硫基化反应以及多步骤序列中的有效催化剂，这需要三重态敏化剂和氢原子抽象剂的组合活性。
• Synthesis of 3,4-fused cycloalkanopyrroles by 1,3-dipolar cycloaddition
  作者：James M. Kelly、Finian J. Leeper

  DOI：10.1016/j.tetlet.2011.12.013

  日期：2012.2

  The synthesis of a number of 3,4-fused cycloalkanopyrroles bearing substituents on the cycloalkane ring was accomplished by 1,3-dipolar cycloaddition. The yield of the cyclization appeared to depend on the base-sensitivity of the Michael acceptor, but the method is applicable across a broad range of cyclic alpha,beta-unsaturated ketone esters. Functional group transformations can be undertaken following pyrrole synthesis to increase the diversity of cycloalkanopyrroles accessible by this method. One pyrrole thus made is a diester of a conformationally-constrained analogue of porphobilinogen, the precursor of the natural tetrapyrroles. (C) 2011 Elsevier Ltd. All rights reserved.