2E,4E-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-penta-2,4-dienoate | 161091-10-7

• 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: 2E,4E-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-penta-2,4-dienoate
• 英文别名: (2E,4E)-Methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dienoate；methyl (2E,4E)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dienoate
• CAS: 161091-10-7
• 化学式: C₁₂H₁₉BO₄
• 分子量: 238.091
• InChiKey: VFZNOYYZULSTJN-CDJQDVQCSA-N

物化性质

• 沸点：
  264.5±42.0 °C(Predicted)
• 密度：
  1.02±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2E,4E-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-penta-2,4-dienoate 、 亚硝基苯 以 甲醇 为溶剂， 反应 22.0h， 以26%的产率得到methyl 1-phenyl-1H-pyrrole-2-carboxylate
  参考文献：
  名称：

  Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds

  摘要：

  A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp(2) boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp(3) boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. H-1 and B-11 NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition elimination sequence.

  DOI：

  10.1021/acs.joc.5b00593
• 作为产物：
  描述：

  甲氧羰基亚甲基三苯基正膦 、 3-boronoacrolein pinacolate 以 甲醇 为溶剂， 生成 2Z,4E-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-penta-2,4-dienoate 、 2E,4E-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-penta-2,4-dienoate
  参考文献：
  名称：

  Rasset-Deloge, Christine; Vaultier, Michel, Bulletin de la Societe Chimique de France, 1994, vol. 131, p. 919 - 925

  摘要：

  DOI：