dimethyl 3-methoxyitaconate | 174644-41-8

• 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: dimethyl 3-methoxyitaconate
• 英文别名: dimethyl 2-methoxy-3-methylenesuccinate；Dimethyl 2-methoxy-3-methylidenebutanedioate
• CAS: 174644-41-8
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: OFKSPUQKYFBNKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  dimethyl 3-methoxyitaconate 生成 dimethyl 2-methoxy-3-methylbutanedioate
  参考文献：
  名称：

  BROWN, JOHN M.;GUTTING, IAN;JAMES, ALUN P., BULL. SOC. CHIM. FR.,(1988) N 1, 211-217

  摘要：

  DOI：
• 作为产物：
  描述：

  dimethyl (Z)-2-(bromomethyl)fumarate 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 dimethyl 3-methoxyitaconate
  参考文献：
  名称：

  Easy Conversion of Dimethylα-(Bromomethyl)fumarate into Functionalized Allyl Ethers Mediated by DABCO

  摘要：

  New functionalized allyl ethers were obtained in good yields following the mild selective reaction of different alcohols with allyl bromide in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) and a catalytic amount of triethylamine (TEA) at room temperature.

  DOI：

  10.1080/00397911.2015.1093144

文献信息

• Synthesis of Postulated Molecular Probes:  Stereoselective Free-Radical-Mediated <i>C</i>-Glycosylation in Tandem with Hydrogen Transfer
  作者：Yvan Guindon、Mohammed Bencheqroun、Abderrahim Bouzide

  DOI：10.1021/ja046389y

  日期：2005.1.1

  employing an addition reaction in tandem with a hydrogen-transfer reaction for the elaboration of C-glycoside-based sialyl Lewis X (sLe(X)) analogues. Significant stereocontrol was noted when alkyl radicals were reacted with a series of alkoxytaconates. Transition states were proposed to explain the obtained selectivity. Further reaction between an anomeric-centered fucosyl-derived radical and a galactosylated

  本文报道了一种策略，该策略采用与氢转移反应串联的加成反应来制备基于 C-糖苷的唾液酸路易斯 X (sLe(X)) 类似物。当烷基自由基与一系列烷氧基taconates 反应时，注意到显着的立体控制。提出了过渡态来解释所获得的选择性。以异头物为中心的岩藻糖基衍生自由基与半乳糖基化羟基他康酸酯之间的进一步反应提供了容易获得 C,O-二糖苷作为 sLe(X) 的模拟物。在这种情况下，在串联过程中使用自由基中间体以高非对映选择性创建了两个 1,3 距离的立体中心。
• Dimethyl 2-(tosylmethyl)fumarate: An allyl sulfone as electrophilic reagent for the synthesis of itaconate ester derivatives
  作者：Rafael Chinchilla、Nuria Galindo、Carmen Nájera

  DOI：10.1016/0040-4020(95)00937-x

  日期：1996.1

  The reaction of dimethyl 2-(tosylmethyl)fumarate (6), prepared by iodosulfonylation-dehydroiodination of dimethyl itaconate, with carbonucleophiles or sodium methoxide allows the direct synthesis of 3-substituted itaconate ester derivatives 8 via a SN2′ pathway. When sodium thiolates are used as nucleophiles dimethyl 2-(alkylthiomethyl)fumarates 9 or alkylthiomethylene butanoates 10 are obtained via

  二甲基-2-（甲苯磺酰基甲基）富马酸酯（6），由衣康酸二甲酯iodosulfonylation-脱碘化氢制备，carbonucleophiles或甲醇钠的反应允许3-取代的衣康酸酯衍生物的直接合成8经由A S Ñ 2'通路。当硫醇钠被用作亲核试剂2-（烷基硫代）富马酸酯9个或alkylthiomethylene丁酸酯10经由双S得到Ñ 2'处理过程。在吡咯烷和环戊酮烯胺的情况下，分别获得相应的二氨基衍生物11和双环[3.2.1]酮12。
• New Selective Synthesis of Dimethyl 3-Alkylamino Itaconates
  作者：Aïcha Arfaoui、Feten Béji、Taïcir Ben Ayed、Hassen Amri

  DOI：10.1080/00397910802213786

  日期：2008.10.22

  Abstract The ammonium 6 salt resulting from the reaction of the DABCO and the allyl bromide 2 was converted with good yields into a new family of dimethyl 3-amino itaconates 5.

  摘要 DABCO 与烯丙基溴 2 反应生成的铵 6 盐以良好的收率转化为新的 3-氨基衣康酸二甲酯 5 家族。
• Joint Experimental/Theoretical Investigation of the Chemoselective Iridium(III) Metallacycle-Catalyzed Reduction of Substituted γ-Lactams by Et₃SiH
  作者：Halima Khadraoui、Chunchesh Malangi Gajendramurthy、Sara Figueirêdo de Alcântara Morais、Yann Cornaton、Hédi M’rabet、Philippe Bertani、Aïcha Arfaoui、Jean-Pierre Djukic

  DOI：10.1021/acs.organomet.4c00044

  日期：——

  of the catalyzed reduction of a series of variously substituted γ-lactams by Et3SiH mediated by a pentamethylcyclopentadienyl iridacyclic acetonitrilo salt derived from benzo[h]quinoline. Introduction of an unsaturation within the 5-membered ring of the γ-lactam annihilates the precedence of the amide function over the capture of the silylium cation, which results in a lower chemoselectivity. Monitoring

  本研究探讨了由苯并[ h ]喹啉衍生的五甲基环戊二烯基环乙腈盐介导的 Et 3 SiH 催化还原一系列不同取代的 γ-内酰胺的化学选择性。在 γ-内酰胺 5 元环内引入不饱和度会消除酰胺官能团相对于硅阳离子捕获的优先性，从而导致较低的化学选择性。通过1 H NMR 光谱随时间监测带有羧酸酯附加物的 γ-内酰胺的催化还原，揭示了内酰胺酰胺先前氢化硅烷化的伪零级动力学。在该初级氢化硅烷化反应之后，所形成的中间体按照伪一级速率定律完全转化为吡咯烷。在无水条件下，当γ-内酰胺的酰胺官能团完全还原羰基官能团时，侧酯官能团的氢化硅烷化仅发生在后期。 DFT 研究表明，化学选择性受 (1) 有机底物对三乙基硅鎓阳离子（通过 Ir(III) 催化剂亲电活化 Et 3 SiH 产生）的亲和力和 (2)原位形成的能力的影响。氢化铱(III)中间体将氢化物转移到活化的底物上。
• A convenient synthesis of 3,4-cis-disubstituted pyrrolidin-2-ones
  作者：Aïcha Arfaoui、Fatma Saâdi、Youssef Ben Smida、Youssef Arfaoui、Adel Nefzi、Hassen Amri

  DOI：10.1016/j.tetlet.2014.11.023

  日期：2015.1

  The conjugate addition of primary amines in methanol at 0 degrees C to the difunctionalized O-methyl allyl ether, prepared from dimethyl alpha-(bromomethyl)fumarate, provides an adduct which cyclizes via a 5-exo-trig process to yield a new family of 3,4-cis-disubstituted pyrrolidin-2-ones in high yields. (C) 2014 Elsevier Ltd. All rights reserved.