dimethyl β-ethyl-α-methylenesuccinate | 110578-24-0

• 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 β-ethyl-α-methylenesuccinate
• 英文别名: dimethyl 2-ethyl-3-methylenebutanedioate；Dimethyl 2-ethyl-3-methylidenebutanedioate
• CAS: 110578-24-0
• 化学式: C₉H₁₄O₄
• 分子量: 186.208
• InChiKey: KQTYDQYHIJGPLH-UHFFFAOYSA-N

物化性质

• 沸点：
  229.2±15.0 °C(Predicted)
• 密度：
  1.038±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl β-ethyl-α-methylenesuccinate 、 苄胺 以 甲醇 、 水 为溶剂， 生成 trans-1-benzyl-3-ethyl-4-methoxycarbonyl pyrrolidin-2-one 、 cis-1-benzyl-3-ethyl-4-methoxycarbonyl pyrrolidin-2-one
  参考文献：
  名称：

  (Z)-Dimethyl α-(bromomethyl)fumarate, an efficient intermediate for the selective synthesis of dimethyl 3-alkyl itaconates and 2-alkyl 3-carbomethoxy-γ-lactams

  摘要：

  (Z)-Dimethyl alpha-(bromomethyl)fumarate 2 proved to be an efficient precursor of 3-substituted itaconic acid esters 3 via its reaction with magnesium dialkylcuprates. Some hindered esters 3 can be used for the diastereoselective synthesis of alpha-alkylated-beta-methoxycarbonyl-gamma-lactams 6. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00118-0
• 作为产物：
  描述：

  Dimethyl 2-[(dimethylamino)methyl]-3-ethylbutanedioate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 碘甲烷 作用下， 生成 dimethyl β-ethyl-α-methylenesuccinate
  参考文献：
  名称：

  A General Approach to Substituted Itaconate Esters

  摘要：

  A general approach to the synthesis of various itaconates including 3-substituted esters is presented. The complementarity of the approach is also shown.

  DOI：

  10.1080/00397919308013789

文献信息

• 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。
• γ-Lactonic and Linear Carboxylic Acids from Cultured Lichen Mycobionts of Graphis scripta
  作者：Takao Tanahashi、Nobuo Hamada、Yukiko Takenaka

  DOI：10.3987/com-14-13107

  日期：——

  Spore-derived mycobionts of the lichen Graphis scripta collected in Nikko, Japan, were cultivated on a malt-yeast extract medium supplemented with 10% sucrose to produce three new carboxylic acids 1-3. Their structures were characterized by chemical and spectroscopic methods. These compounds are prototypes of characteristic lichen substances, gamma-lactonic and linear carboxylic acids with a long side chain, and were obtained as enantiomeric mixtures.
• SAKAI MUTSUJI; SHIRAKAWA KENJI; NISHI ICHIRO; SAKAKIBARA YASUMASA; UCHINO+, KETO KOGEHJ SEHNI DAJGAKU. SEHNI GAKUBU GAKUDZYUTSU XOKOKU, BULL. FAS. TE+
  作者：SAKAI MUTSUJI、 SHIRAKAWA KENJI、 NISHI ICHIRO、 SAKAKIBARA YASUMASA、 UCHINO+

  DOI：——

  日期：——
• (Z)-Dimethyl α-(bromomethyl)fumarate, an efficient intermediate for the selective synthesis of dimethyl 3-alkyl itaconates and 2-alkyl 3-carbomethoxy-γ-lactams
  作者：I. Beltaïef、R. Besbes、F. Ben Amor、H. Amri、M. Villiéras、J. Villiéras

  DOI：10.1016/s0040-4020(99)00118-0

  日期：1999.3

  (Z)-Dimethyl alpha-(bromomethyl)fumarate 2 proved to be an efficient precursor of 3-substituted itaconic acid esters 3 via its reaction with magnesium dialkylcuprates. Some hindered esters 3 can be used for the diastereoselective synthesis of alpha-alkylated-beta-methoxycarbonyl-gamma-lactams 6. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A General Approach to Substituted Itaconate Esters
  作者：Paul Dowd、Bogdan K. Wilk

  DOI：10.1080/00397919308013789

  日期：1993.8

  A general approach to the synthesis of various itaconates including 3-substituted esters is presented. The complementarity of the approach is also shown.