2-Methoxy-5-phenyl-3,4-bis-[(triisopropylsilanyl)-ethynyl]-furan | 708208-15-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Methoxy-5-phenyl-3,4-bis-[(triisopropylsilanyl)-ethynyl]-furan
• 英文别名: 2-[2-Methoxy-5-phenyl-4-[2-tri(propan-2-yl)silylethynyl]furan-3-yl]ethynyl-tri(propan-2-yl)silane；2-[2-methoxy-5-phenyl-4-[2-tri(propan-2-yl)silylethynyl]furan-3-yl]ethynyl-tri(propan-2-yl)silane
• CAS: 708208-15-5
• 化学式: C₃₃H₅₀O₂Si₂
• 分子量: 534.93
• InChiKey: ORINBODFGLCTJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.09
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  22.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Methoxy-5-phenyl-3,4-bis-[(triisopropylsilanyl)-ethynyl]-furan 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以57%的产率得到3,4-Diethynyl-2-methoxy-5-phenyl-furan
  参考文献：
  名称：

  Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

  摘要：

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.

  DOI：

  10.1021/ja049836i
• 作为产物：
  描述：

  1-(triisopropylsilyl)butadiyne 在 盐酸羟胺 、 正丁胺 、 copper(l) chloride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 2-Methoxy-5-phenyl-3,4-bis-[(triisopropylsilanyl)-ethynyl]-furan
  参考文献：
  名称：

  Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes

  摘要：

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.

  DOI：

  10.1021/ja049836i

文献信息

• Contingency and Serendipity in the Reactions of Fischer Carbene Complexes with Conjugated Triynes
  作者：May Xiao-Wu Jiang、Manish Rawat、William D. Wulff

  DOI：10.1021/ja049836i

  日期：2004.5.1

  The first examples of reactions of Fischer carbene complexes with triynes are reported. The regioselectivity of the reaction of the two different alkyne functions in the symmetrical triyne depends on the nature of the substituent of the triyne. Bis-silyl-substituted triynes react at the central alkyne unit, whereas bis-aryl- and bis-alkyl-substituted triynes react at the end alkyne unit. The reaction of a Fischer carbene complex with a phenyl substituent also reacts with a bis-silyl-substituted triyne at the central alkyne unit but gives a furan product rather than the normal phenol product. It was also demonstrated that all three of the alkyne units in conjugated triynes could react in turn with a Fischer carbene complex to give access to trisquinones.