methyl 2-(acetoxy(furan-2-yl)methyl)acrylate | 124957-39-7

• 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: methyl 2-(acetoxy(furan-2-yl)methyl)acrylate
• 英文别名: Methyl 2-[acetyloxy(furan-2-yl)methyl]prop-2-enoate
• CAS: 124957-39-7
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: OGIHVUSJZGKCPS-UHFFFAOYSA-N

物化性质

• 沸点：
  96 °C(Press: 0.02 Torr)
• 密度：
  1.178±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  65.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-(acetoxy(furan-2-yl)methyl)acrylate 在 三乙烯二胺 、 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 3.17h， 生成 anti-4-furan-2-yl-6-methyl-3-methylenetetrahydropyran-2-one
  参考文献：
  名称：

  Persistent splenomegaly in an adult female with homozygous sickle cell anemia

  摘要：

  Sickle cell anemia (SCA) is associated with repeated episodes of erythrostasis in the spleen, which lead to thrombosis and infarction of the spleen resulting in "autosplenectomy" which is usually complete by 8 years of age.We present a case of a 22-year-old female who presented with complaints of fever, bone pain and joint swelling. On examination she had pallor, icterus and moderate splenomegaly. Her hemoglobin was 7.5g/dl. Peripheral smear showed many sickled red cells. Slide test for sickling was positive with 2% sodium metabisulphite. Hemoglobin electrophoresis revealed a single band in the hemoglobin S, D, and G region. No band was seen in the HbA & HbA(2) region. HbF level was 0%. USG showed an enlarged spleen with few defined hypoechoeic lesion.We present this case because of rarity of association of homozygous SCA with splenomegaly in this age group, the confusion that echogenic lesions in spleen can create and to emphasize the risk of sequestration crises, which remains in such cases.

  DOI：

  10.1080/01650420500328365
• 作为产物：
  描述：

  糠醛 在 三乙烯二胺 、 4-二甲氨基吡啶 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 1.5h， 生成 methyl 2-(acetoxy(furan-2-yl)methyl)acrylate
  参考文献：
  名称：

  催化不对称加氢高效合成杂环和脂环族β2-氨基酸衍生物

  摘要：

  通过三步转化，包括Baylis-Hillman反应，O-乙酰化和随后的烯丙基胺化，可以方便地合成一类有价值的新型杂环和脂环族手性α-氨基甲基丙烯酸酯。相应的新颖β 2 -氨基苯甲酸衍生物，用使用该催化剂的铑（ET-DUPHOS）（ET-DUPHOS = 2'，5'，2''，5''优异的对映选择性和高的产率通过催化不对称氢化制备-四乙基-1,2-双（膦酰基戊基苯））在温和的反应条件下（高达ee的99％）并且S / C = 1000）。研究了底物对对映选择性和反应性的影响，并报道了在Rh-Duphos体系下高效进行β-取代的α-氨基甲基丙烯酸酯的对映选择性加氢的最合适的底物构型。当前协议提供了一种非常实用的，容易的，且可扩展为杂环和脂环β制备方法2的α-氨基酸和它们的衍生物。

  DOI：

  10.1002/asia.201300339

文献信息

• <i>N</i>-Bromosuccinimide-Mediated Radical Cyclization of 3-Arylallyl Azides: Synthesis of 3-Substituted Quinolines
  作者：Wei-Xia Wang、Qing-Zhao Zhang、Tian-Qi Zhang、Zhan-Shan Li、Wei Zhang、Wei Yu

  DOI：10.1002/adsc.201400637

  日期：2015.1.12

  an effective means to convert methyl 2‐(azidomethyl)‐3‐arylpropenoates and 2‐(azidomethyl)‐3‐arylacrylonitriles to the corresponding iminyl radicals via α‐hydrogen abstraction and subsequent extrusion of dinitrogen. Thus formed iminyl radicals then undergo intramolecular ortho attack on the aryl ring, affording methyl quinoline‐3‐carboxylates and quinoline‐3‐carbonitriles respectively.

  N-溴代琥珀酰亚胺的可见光照射是一种有效的手段，可通过α-氢提取并随后挤出二氮，将2-（叠氮基甲基）-3-芳基丙烯酸甲酯和2-（叠氮基甲基）-3-芳基丙烯腈转化为相应的亚氨基。如此形成的亚氨基自由基随后在芳基环上进行分子内邻位攻击，分别得到喹啉-3-羧酸甲酯和喹啉-3-腈。
• Synthesis and structural features of new [5,7] orthocyclophanes, [7,7] cyclophanes and corresponding macrobicyclic cryptophanes.
  作者：Patrick Bauchat、Nathalie Le Bras、Luc Rigal、André Foucaud

  DOI：10.1016/s0040-4020(01)85265-0

  日期：1994.1

  Baylis-Hillman reaction of dialdehydes with methyl acrylate, followed by acetylation of the resulting diols gave diacetates 3, 14, 16 and 20. Treated with ammonia, these diacetates afforded new cyclophanes and the corresponding macrobicyclic cryptophanes. Conformational analysis of the cyclophanes was described.

  与丙烯酸甲酯二醛的的Baylis-Hillman反应，接着将得到的二元醇的乙酰化，得到二乙酸酯3，14，16和20。用氨处理后，这些二乙酸酯提供了新的环烷和相应的大双环隐烷。描述了环烷的构象分析。
• The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis
  作者：Xiaojun Dai、Dongping Cheng、Baochuan Guan、Wenjuan Mao、Xiaoliang Xu、Xiaonian Li

  DOI：10.1021/jo501097b

  日期：2014.8.1

  Catalyzed by Ru(bpy)3(BF4)2, the photoredox coupling of tertiary amines with acrylate derivatives including Baylis–Hillman adducts under visible light irradiation was successfully established. The scope of the substrates was broad, and thus an array of γ-aminobutyric ester derivatives was obtained in moderate to good yields.

  通过Ru（bpy）3（BF 4）2催化，成功建立了叔胺与丙烯酸酯衍生物（包括Baylis-Hillman加合物）在可见光下的光氧化还原偶联。底物的范围很广，因此以中等至良好的产率获得了一系列的γ-氨基丁酸酯衍生物。
• The coupling reaction of α-silylamines with Baylis-Hillman adducts by visible light photoredox catalysis
  作者：He Zhao、Niannian Ni、Xiaonian Li、Dongping Cheng、Xiaoliang Xu

  DOI：10.1016/j.tetlet.2020.152746

  日期：2021.2

  The preparation of N-containing α,β-unsaturated carboxylate derivatives from α-silylamine and Baylis-Hillman adducts under visible light irradiation was reported. The formation of α-aminoalkyl radical is regioselective compared with the previous reports. The reaction was successfully performed without additional additives under mild conditions.

  报道了在可见光照射下由α-甲硅烷基胺和Baylis-Hillman加合物制备含N的α，β-不饱和羧酸酯衍生物。与先前的报道相比，α-氨基烷基的形成具有区域选择性。在温和条件下，无需添加其他添加剂即可成功进行反应。
• Synthesis of 3,4,5-Trisubstituted Isoxazoles from Morita-Baylis-Hillman Acetates by an NaNO₂/I₂-Mediated Domino Reaction
  作者：Shashikant U. Dighe、Sushobhan Mukhopadhyay、Shivalinga Kolle、Sanjeev Kanojiya、Sanjay Batra

  DOI：10.1002/anie.201504529

  日期：2015.9.7

  3‐nitro‐5‐(aryl/alkyl)isoxazole‐4‐carboxylates is described. In a cascade event, initial Michael addition of NaNO2 to the MBH acetate furnishes the allylnitro intermediate which undergoes I2‐catalyzed oxidative α‐CH nitration of the nitromethyl subunit followed by [3+2] cycloaddition to afford the title compounds. Structural elaborations of these highly substituted isoxazoles by SNAr reactions and

  本文描述了一种有效的NaNO 2 / I 2介导的Morita-Baylis-Hillman（MBH）乙酸盐单酯转化为3-硝基--5-（芳基/烷基）异恶唑-4-羧酸烷基酯的方法。在一个级联事件，初始迈克尔加成纳米2到MBH醋酸配料其经历我的allylnitro中间2催化的氧化α-C 的硝基甲基亚基h的硝化，接着[3 + 2]环加成，得到标题化合物。这些高度取代的异恶唑通过S N Ar反应和氢解进行结构精制可以得到有用的产品。