(R,S)-(Z)-3-(2-Tetrahydrofuryl)propenoic acid methyl ester | 122592-49-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R,S)-(Z)-3-(2-Tetrahydrofuryl)propenoic acid methyl ester
• 英文别名: methyl (Z)-3-(tetrahydrofuran-2-yl)-2-propenoate；(Z)-methyl 3-(2-tetrahydrofuranyl)propenoate；cis-2-(Tetrahydro-2-furyl)-acrylsaeure-methylester；methyl (Z)-3-(oxolan-2-yl)prop-2-enoate
• CAS: 122592-49-8
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: PSBXQQMOTMFAIO-PLNGDYQASA-N

物化性质

• 沸点：
  214.2±23.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,S)-(Z)-3-(2-Tetrahydrofuryl)propenoic acid methyl ester 在 吡啶 、 sodium acetate 、 二异丁基氢化铝 、 silver nitrate 、 二甲基亚砜 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.5h， 生成 [(Z)-3-(oxolan-2-yl)prop-2-enyl] 2-oxoacetate
  参考文献：
  名称：

  Stereoselective intramolecular nitrone cycloadditions promoted by an allylic stereocenter

  摘要：

  DOI：

  10.1021/jo00293a040
• 作为产物：
  描述：

  四氢呋喃-2-甲醛 、 O,O'-双(2,2,2-三氟乙基)磷乙酸甲酯 在 potassium hydride 作用下， 生成 (R,S)-(Z)-3-(2-Tetrahydrofuryl)propenoic acid methyl ester
  参考文献：
  名称：

  Stereoselective intramolecular nitrone cycloadditions promoted by an allylic stereocenter

  摘要：

  DOI：

  10.1021/jo00293a040

文献信息

• Manganese dioxide can oxidise unactivated alcohols under in situ oxidation–Wittig conditions
  作者：Leonie Blackburn、Xudong Wei、Richard J. K. Taylor

  DOI：10.1039/a903980e

  日期：——

  The in situ alcohol oxidation–Wittig reaction using manganese dioxide as the oxidant has been applied to semi-activated and, for the first time, unactivated alcohols to furnish the corresponding α,β-unsaturated esters.

  以二氧化锰为氧化剂的原位醇氧化-维蒂希反应已应用于半活化醇，并首次应用于未活化醇，以生成相应的δ,δ-不饱和酯。
• Direct S0 → Tn Transition under Visible Light Irradiation Enabling Synthesis of a Pseudoindoxyl Scaffold
  作者：Masaya Nakajima、Sho Nagasawa、Keita Yamazaki、Tomohiro Yazawa、Honoka Yoneyama、Yuko Kotaka、Tetsuhiro Nemoto

  DOI：10.1021/acs.orglett.4c00957

  日期：2024.4.19

  products. Its light-absorption properties make it useful for the design of functional molecules. However, versatile synthesis methods have not yet been reported. In this report, we present a versatile synthetic method for pseudoindoxyls using the direct S0 → Tn transition under visible light irradiation. We also discuss the application of pseudoindoxyls as photocatalysts.

  假吲哚酚是在各种天然产物中发现的部分骨架。其光吸收特性使其可用于功能分子的设计。然而，通用的合成方法尚未见报道。在本报告中，我们提出了一种在可见光照射下利用直接 S 0 → T n跃迁合成假吲哚酚的通用方法。我们还讨论了假吲哚酚作为光催化剂的应用。
• Reductive cleavage reaction of .gamma.-functionalized .alpha.,.beta.-unsaturated esters and halomethyls mediated with magnesium in methanol
  作者：Chwang Siek Pak、Eun Lee、Ge Hyeong Lee

  DOI：10.1021/jo00058a038

  日期：1993.3

  Reductive cleavage of various types of C-O and C-N bonds tethered to alpha,beta-unsaturated esters and halomethyls was mediated with magnesium in methanol, which provided a facile method for the synthesis of delta-hydroxy or delta-amino beta,gamma-unsaturated esters and allylic alcohols. Regardless of the geometry (E or Z) of the alpha,beta-unsaturated esters, 1a-b, 5a-c, 11, 13, and 23, the cleavage product obtained was exclusively the E isomer of the corresponding deconjugated hydroxy and amino esters. The steric bias and ring strain of 15, 17, and 21 gave rise to a product mixture of E and Z isomers.
• Priepke, Henning; Brueckner, Reinhard, Chemische Berichte, 1990, vol. 123, # 1, p. 153 - 168
  作者：Priepke, Henning、Brueckner, Reinhard

  DOI：——

  日期：——
• Cobalt-catalyzed direct C–C bond formation between tetrahydrofuran and alkynes
  作者：Li Chen、Jiajia Yang、Lin Li、Zhiqiang Weng、Qiang Kang

  DOI：10.1016/j.tetlet.2014.09.042

  日期：2014.10

  We aimed to describe an efficient CoCl2-catalyzed direct C-C bond formation of tetrahydrofuran (THF) with various alkynes in the presence of tert-butyl hydroperoxide and catalytic amount of acid to obtain vinyl-substituted THFs. Mono- and di-substituted alkynes were suitable for this transformation. (C) 2014 Elsevier Ltd. All rights reserved.