dimethyl (E)-2-butylidenesuccinate | 254098-83-4

• 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 (E)-2-butylidenesuccinate
• 英文别名: dimethyl (2E)-2-butylidenebutanedioate
• CAS: 254098-83-4
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: IGOBMABWRSCIAA-SOFGYWHQSA-N

物化性质

• 沸点：
  256.6±15.0 °C(Predicted)
• 密度：
  1.032±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 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 (E)-2-butylidenesuccinate 在 palladium on activated charcoal 氢气 、 lithium aluminium tetrahydride 作用下， 以 乙酸乙酯 、 乙醚 为溶剂， 25.0 ℃ 、275.79 kPa 条件下， 反应 17.0h， 以70%的产率得到2-丁基丁烷-1,4-二醇
  参考文献：
  名称：

  Nitroalkanes as a new source of 2-alkylidene-1,4-diols, in two steps

  摘要：

  A variety of 3-alkylidene-1,4-diols have been conveniently prepared, in two steps, by conjugate addition of a nitroalkane to the appropriate enedione derivatives under basic conditions (DBU), followed by chemoselective reduction (LiAlH4/Et2O) of the carbonyl functionalities of the Michael adduct, obtained after elimination of nitrous acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00829-7
• 作为产物：
  描述：

  1-硝基丁烷 、 马来酸二甲酯 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以94%的产率得到dimethyl (E)-2-butylidenesuccinate
  参考文献：
  名称：

  Nitroalkanes as a new source of 2-alkylidene-1,4-diols, in two steps

  摘要：

  A variety of 3-alkylidene-1,4-diols have been conveniently prepared, in two steps, by conjugate addition of a nitroalkane to the appropriate enedione derivatives under basic conditions (DBU), followed by chemoselective reduction (LiAlH4/Et2O) of the carbonyl functionalities of the Michael adduct, obtained after elimination of nitrous acid. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00829-7

文献信息

• Regio- and stereoselective selenium dioxide allylic oxidation of (E)-dialkyl alkylidenesuccinates to (Z)-allylic alcohols: Synthesis of natural and unnatural butenolides
  作者：Ramesh M. Patel、Vedavati G. Puranik、Narshinha P. Argade

  DOI：10.1039/c1ob05709j

  日期：——

  allylic alcohol formation of dialkyl alkylidenesuccinates has been demonstrated to accomplish one-step syntheses of several essential butenolides and fused butenolidesvia an unusual E- to Z- carbon–carbon double bond isomerisation followed by the lactonization pathway. The observed regio- and stereoselective SeO2 allylic oxidation protocol has also been extended to the diastereoselective total synthesis

  首次证明SeO 2诱导的二烷基亚烷基琥珀酸二烷基酯的（Z）选择性烯丙醇的形成通过不寻常的E-到Z-碳-碳双键异构化然后进行内酯化来完成几种基本丁烯内酯和稠合丁烯内酯的一步合成。途径。观察到的区域和立体选择性SeO 2烯丙基氧化方案也已扩展到生物活性天然产物异内酯的非对映选择性全合成，其直接转化为薄荷酸内酯和γ-内酯分子内重排为δ-内酯的例子。
• Synthesis of (E)-3-Alkylidenepyrrolidines by Nucleophilic Ring Closure of (E)-2-Alkylidene-1,4-diol Derivatives
  作者：Roberto Ballini、Giovanna Bosica、Aldo Masè、Marino Petrini

  DOI：10.1002/1099-0690(200008)2000:16<2927::aid-ejoc2927>3.3.co;2-p

  日期：2000.8