dimethyl allyl(4-methoxycarbonyloxy-2E-butenyl)malonate | 158627-64-6

• 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 allyl(4-methoxycarbonyloxy-2E-butenyl)malonate
• 英文别名: dimethyl (E)-<4-((methoxycarbonyl)oxy)but-2-enyl>-2-(prop-2-enyl)propanedioate；(E)-dimethyl 2-allyl-2-(4-((methoxycarbonyl)oxy)but-2-en-1-yl)malonate；dimethyl 2-[(E)-4-methoxycarbonyloxybut-2-enyl]-2-prop-2-enylpropanedioate
• CAS: 158627-64-6
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: WFEBGRYFXOXQOE-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl allyl(4-methoxycarbonyloxy-2E-butenyl)malonate 、 联硼酸频那醇酯 在 potassium tert-butylate 、 palladium diacetate 、 1,3-双(2,4,6-三甲基苯基)氯化咪唑 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 以70%的产率得到(E)-dimethyl 2-allyl-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)but-2-en-1-yl)malonate
  参考文献：
  名称：

  Ligand-controlled divergent formation of alkenyl- or allylboronates catalyzed by Pd, and synthetic applications

  摘要：

  Pd催化的含炔基的烯丙基碳酸酯与B2(pin)2的反应会产生烯基硼酸酯通过级联硼化环化反应，或者产生烯丙基硼酸酯。反应结果受合适配体的选择控制。硼酸酯已应用于许多合成应用中。

  DOI：

  10.1039/c4cc04092a
• 作为产物：
  描述：

  烯丙基丙二酸二甲酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醚 、 正己烷 、 paraffin 为溶剂， 反应 11.0h， 生成 dimethyl allyl(4-methoxycarbonyloxy-2E-butenyl)malonate
  参考文献：
  名称：

  Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues

  摘要：

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.

  DOI：

  10.1016/s0040-4020(01)85639-8

文献信息

• Rhodium(I)-Catalyzed ‘Metallo-Ene’ Cyclizations/β-Eliminations
  作者：Wolfgang Oppolzer、Alois Fürstner

  DOI：10.1002/hlca.19930760618

  日期：1993.9.22

  Octadienyl carbonates 5 provide cyclic 1,4-dienes 6 when treated with Rh1 complexes (1–10 mol-%) at 80°. Similar cyclization of cyclohexenyl acetate 8 affords cis- fused hexahydroindene 9. Analogous ring closures of nonadienyl carbonate 10 yield preferably the cis-divinypyrrolidine 11 with Rh1 catalysis but the trans-isomer 12 when catalyzed by Pd0. Azaoctadienyl carbonate 5a undergoes elimination

  当在80°下用Rh 1配合物（1-10 mol％）处理时，碳酸辛二烯酯5可提供环状1,4-二烯6。环己烯基乙酸酯8的类似环化反应可得到顺式稠合六氢茚9。碳酸壬二烯基酯10的类似的闭环优选在Rh 1催化下产生顺式-二乙烯基吡咯烷11，而在Pd 0催化下则形成反式异构体12。碳酸氮杂二烯基酯5a被[RhH（PPh 3）4消除]（5 mol％，80°）在MeCN中得到无环三烯。7。
• Palladium(0)-catalyzed cyclization-carbonylation of 2,7-octadienyl acetate and homologues
  作者：Masahiko Terakado、Kouya Murai、Masahiro Miyazawa、Keiji Yamamoto

  DOI：10.1016/s0040-4020(01)85639-8

  日期：——

  The palladium(0)-catalyzed carbonylations, in acetic acid as a necessary solvent, of 2,7-octadienyl acetate and homologues via pi-allylpalladium species were preceded by their intramolecular oelfin insertion to form mixtures of cis/trans-2-vinylcyclopentylacetyl- and cis/trans-cyclohexylacetylpalladium intermediates, which undergo further the intramolecular (5-exo) Heck reaction to give bicyclo-[3.3.0] and [4.3.0] skeletons, respectively, except for one case affording trans-2-vinylcyclopentylacetic acid as a major product.
• Ligand-controlled divergent formation of alkenyl- or allylboronates catalyzed by Pd, and synthetic applications
  作者：Alicia Martos-Redruejo、Ruth López-Durán、Elena Buñuel、Diego J. Cárdenas

  DOI：10.1039/c4cc04092a

  日期：——

  Pd-catalysed reactions of allyl carbonates containing alkynes with B2(pin)2 afford either alkenylboronates by cascade borylative cyclisation, or allylboronates. The reaction outcome is controlled by a suitable choice of ligands. Boronates have been applied to a number of synthetic applications.

  Pd催化的含炔基的烯丙基碳酸酯与B2(pin)2的反应会产生烯基硼酸酯通过级联硼化环化反应，或者产生烯丙基硼酸酯。反应结果受合适配体的选择控制。硼酸酯已应用于许多合成应用中。