(Z)-1-methoxybut-1-ene-3-yne | 191597-76-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (Z)-1-methoxybut-1-ene-3-yne
• 英文别名: [(Z)-4-methoxybut-3-en-1-ynyl]-diphenylphosphane
• CAS: 191597-76-9
• 化学式: C₁₇H₁₅OP
• 分子量: 266.279
• InChiKey: DWUGOCGCMQSRBB-ZSOIEALJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (Z)-1-methoxybut-1-ene-3-yne 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 C₁₆H₁₀LiP
  参考文献：
  名称：

  (Z)-1-methoxy-4-(diphenylphosphino) but-1-ene-3-yne: A versatile synthon for unsymmetrically substituted (diphenylphosphino) diacetylene derivatives

  摘要：

  An efficient synthesis of Ph2P-C equivalent to C-C equivalent to C-Li, 1, was found, starting from commercially available (Z)-1-methoxybut-1-ene-3-yne and its diphenylphosphino derivative 2. The lithio compound 1 was condensed with electrophiles to give Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiR3, SnR3, B((NPr)-Pr-i)(2)) 3. Compound 2 was easily transformed into the phosphonium salt 6 and the phosphine oxide 7 using Mel and H2O2 respectively. Derivatives 3 (Z = SiMe3, SnMe3) are reactive at phosphorus and at the Sigma group; complexation with W(CO)(5)THF gave the expected derivatives W(CO)(5)Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiMe3, SnMe3), 10, and in the case of Sigma = SnMe3, coupling reaction between Ph2P-C equivalent to-C-C equivalent to C-SnMe3, 3c, and (eta(5)-IC5H4)Mn(CO)(3) in the presence of PdCl2(CH3CN)(2) as a catalyst gave the complex 11, Ph2P-C equivalent to C-C equivalent to C-(eta(5)-C5H4)Mn(CO)(3).

  DOI：

  10.1016/s0022-328x(96)06655-7
• 作为产物：
  描述：

  (Z)-1-methoxybut-1-en-3-yne 、 二苯基氯化膦 在 正丁基锂 作用下， 生成 (Z)-1-methoxybut-1-ene-3-yne
  参考文献：
  名称：

  (Z)-1-methoxy-4-(diphenylphosphino) but-1-ene-3-yne: A versatile synthon for unsymmetrically substituted (diphenylphosphino) diacetylene derivatives

  摘要：

  An efficient synthesis of Ph2P-C equivalent to C-C equivalent to C-Li, 1, was found, starting from commercially available (Z)-1-methoxybut-1-ene-3-yne and its diphenylphosphino derivative 2. The lithio compound 1 was condensed with electrophiles to give Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiR3, SnR3, B((NPr)-Pr-i)(2)) 3. Compound 2 was easily transformed into the phosphonium salt 6 and the phosphine oxide 7 using Mel and H2O2 respectively. Derivatives 3 (Z = SiMe3, SnMe3) are reactive at phosphorus and at the Sigma group; complexation with W(CO)(5)THF gave the expected derivatives W(CO)(5)Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiMe3, SnMe3), 10, and in the case of Sigma = SnMe3, coupling reaction between Ph2P-C equivalent to-C-C equivalent to C-SnMe3, 3c, and (eta(5)-IC5H4)Mn(CO)(3) in the presence of PdCl2(CH3CN)(2) as a catalyst gave the complex 11, Ph2P-C equivalent to C-C equivalent to C-(eta(5)-C5H4)Mn(CO)(3).

  DOI：

  10.1016/s0022-328x(96)06655-7

文献信息

• (Z)-1-methoxy-4-(diphenylphosphino) but-1-ene-3-yne: A versatile synthon for unsymmetrically substituted (diphenylphosphino) diacetylene derivatives
  作者：Robert J.P. Corriu、Christian Guérin、Bernard J.L. Henner、Agnès Jolivet

  DOI：10.1016/s0022-328x(96)06655-7

  日期：1997.3

  An efficient synthesis of Ph2P-C equivalent to C-C equivalent to C-Li, 1, was found, starting from commercially available (Z)-1-methoxybut-1-ene-3-yne and its diphenylphosphino derivative 2. The lithio compound 1 was condensed with electrophiles to give Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiR3, SnR3, B((NPr)-Pr-i)(2)) 3. Compound 2 was easily transformed into the phosphonium salt 6 and the phosphine oxide 7 using Mel and H2O2 respectively. Derivatives 3 (Z = SiMe3, SnMe3) are reactive at phosphorus and at the Sigma group; complexation with W(CO)(5)THF gave the expected derivatives W(CO)(5)Ph2P-C equivalent to C-C equivalent to C-Sigma (Sigma = SiMe3, SnMe3), 10, and in the case of Sigma = SnMe3, coupling reaction between Ph2P-C equivalent to-C-C equivalent to C-SnMe3, 3c, and (eta(5)-IC5H4)Mn(CO)(3) in the presence of PdCl2(CH3CN)(2) as a catalyst gave the complex 11, Ph2P-C equivalent to C-C equivalent to C-(eta(5)-C5H4)Mn(CO)(3).