3-(3-Hydroxy-3-methylbut-3-ynyl)-4-(methoxymethoxy)benzaldehyde | 173029-70-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3-Hydroxy-3-methylbut-3-ynyl)-4-(methoxymethoxy)benzaldehyde
• 英文别名: 3-(3-Hydroxy-3-methylbut-1-ynyl)-4-(methoxymethoxy)benzaldehyde
• CAS: 173029-70-4
• 化学式: C₁₄H₁₆O₄
• 分子量: 248.279
• InChiKey: HJBFJMQYIUELHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3-Hydroxy-3-methylbut-3-ynyl)-4-(methoxymethoxy)benzaldehyde 在 三氯氧磷 作用下， 以 吡啶 为溶剂， 反应 12.0h， 以38%的产率得到4-(Methoxymethoxy)-3-(3-methylbut-3-en-1-ynyl)benzaldehyde
  参考文献：
  名称：

  New synthetic applications of water-soluble acetate Pd/TPPTS catalyst generated in Situ. evidence for a true Pd(0) species intermediate

  摘要：

  Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)(3) (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65%). Under the same conditions, the sp(2)-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99%). Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling. Furthermore, through a series of kinetic and P-31 NMR experiments, we have demonstrated that a mixture of Pd(OAc)(2) and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)(2)-(TPPTS)(2). A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured. The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition. This complex is considerably less reactive than the corresponding complex generated from PPh(3), probably due to steric effects.

  DOI：

  10.1021/jo00126a037
• 作为产物：
  描述：

  4-羟基-3-碘苯甲醛 在 palladium diacetate 、 trisodium tris(3-sulfophenyl)phosphine phosphorus pentoxide 、 三乙胺 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 3-(3-Hydroxy-3-methylbut-3-ynyl)-4-(methoxymethoxy)benzaldehyde
  参考文献：
  名称：

  New synthetic applications of water-soluble acetate Pd/TPPTS catalyst generated in Situ. evidence for a true Pd(0) species intermediate

  摘要：

  Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)(3) (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65%). Under the same conditions, the sp(2)-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99%). Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling. Furthermore, through a series of kinetic and P-31 NMR experiments, we have demonstrated that a mixture of Pd(OAc)(2) and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)(2)-(TPPTS)(2). A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured. The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition. This complex is considerably less reactive than the corresponding complex generated from PPh(3), probably due to steric effects.

  DOI：

  10.1021/jo00126a037

文献信息

• New synthetic applications of water-soluble acetate Pd/TPPTS catalyst generated in Situ. evidence for a true Pd(0) species intermediate
  作者：Christian Amatore、Errol Blart、Jean Pierre Genet、Anny Jutand、Sandrine Lemaire-Audoire、Monique Savignac

  DOI：10.1021/jo00126a037

  日期：1995.10

  Studies on the sp-sp intermolecular coupling reactions with the palladium water-soluble catalyst prepared in situ from palladium(II) acetate and sulfonated triphenylphosphine P(C6H4-m-SO3Na)(3) (TPPTS) in a homogeneous acetonitrile-water system, without Cu(I) promotor, afford diynes with moderate yields (45-65%). Under the same conditions, the sp(2)-sp coupling of 2-iodophenols or 2-iodoanilines and terminal alkynes followed by intramolecular cyclization gives indolic and furanic products in good yields (60-99%). Under these aqueous conditions, an efficient and short synthesis of eutypine illustrated the synthetic potentiality of the coupling. Furthermore, through a series of kinetic and P-31 NMR experiments, we have demonstrated that a mixture of Pd(OAc)(2) and TPPTS affords spontaneously a palladium(0) complex, through formation of bivalent complex Pd(OAc)(2)-(TPPTS)(2). A detailed mechanism of the reaction has been investigated thoroughly and the pertinent rate constants measured. The resulting palladium(0) complex reacts with phenyl iodide via an oxidative addition. This complex is considerably less reactive than the corresponding complex generated from PPh(3), probably due to steric effects.