3-Methoxycarbonyloxy-2-methylene-butyric acid methyl ester | 141331-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 3-Methoxycarbonyloxy-2-methylene-butyric acid methyl ester
• 英文别名: Methyl 3-methoxycarbonyloxy-2-methylidenebutanoate
• CAS: 141331-23-9
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: FPTUOGVUQAFEFB-UHFFFAOYSA-N

物化性质

• 沸点：
  224.6±33.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：

  一氧化碳 、 3-Methoxycarbonyloxy-2-methylene-butyric acid methyl ester 在 palladium diacetate 、 三苯基膦 作用下， 50.0 ℃ 、2.03 MPa 条件下， 反应 15.0h， 生成 (E)-dimethyl 2-ethylidenesuccinate 、 (Z)-dimethyl 2-ethylidenesuccinate
  参考文献：
  名称：

  Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues

  摘要：

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.

  DOI：

  10.1016/s0040-4020(01)88755-x
• 作为产物：
  描述：

  3-羟基-2-亚甲基丁酸甲酯 、 氯甲酸甲酯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 苯 为溶剂， 以9%的产率得到3-Methoxycarbonyloxy-2-methylene-butyric acid methyl ester
  参考文献：
  名称：

  Stereochemical study on the palladium(O)-catalyzed carbonylation of 3-(methoxycarbonyloxy)-2-methylenealkanoates and analogues

  摘要：

  A series of 3-(alkoxycarbonyloxy)-2-methylenealkanoate (1), a sulfonate (5), and an N,N-dimethylamide (6) were carbonylated using Pd(0) complexes as catalyst to give alkylidenesuccinate (2), and analogues in moderate to good yields. The stereoselectivity for E and Z isomers of carbonylation products was found to differ remarkably, depending on the three types of substrates which always include an electron-withdrawing group. The results are explained in terms of the plausible MM2 simulation through the model compounds.

  DOI：

  10.1016/s0040-4020(01)88755-x

文献信息

• Total Syntheses of Furaquinocin A, B, and E
  作者：Barry M. Trost、Oliver R. Thiel、Hon-Chung Tsui

  DOI：10.1021/ja0364118

  日期：2003.10.1

  A modular approach to the total synthesis of furaquinocins culminated in the total syntheses of furaquinocin A, B, and E. A Pd-catalyzed dynamic kinetic asymmetric transformation (DYKAT) on carbonates derived from Baylis-Hillman adducts, followed by a reductive Heck cyclization allows the enantio- and diastereoselective construction of dihydrobenzofuran 32. Introduction of a double unsatured side chain

  使用交叉复分解或闭环复分解可以实现侧链的立体选择性延伸。获得的后期中间体成功转化为呋喃喹啉A和B。