ethyl(Z)-3-methyl-5-phenyl-2-tributylstannyl-2-penten-4-ynoate | 204651-30-9

• 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: ethyl(Z)-3-methyl-5-phenyl-2-tributylstannyl-2-penten-4-ynoate
• CAS: 204651-30-9
• 化学式: C₂₆H₄₀O₂Sn
• 分子量: 503.312
• InChiKey: ANCOVETWBODAOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.31
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-丁炔酸乙酯 、 苯基乙炔三丁基锡 在 bis(η3-allyl-μ-chloropalladium(II)) catalyst:N[2-(PPh₂)benzylidene]cyclohexylamine 作用下， 以 四氢呋喃 为溶剂， 以29%的产率得到ethyl(Z)-3-methyl-5-phenyl-2-tributylstannyl-2-penten-4-ynoate
  参考文献：
  名称：

  Palladium−Iminophosphine-Catalyzed Alkynylstannylation of Alkynes

  摘要：

  A palladium complex coordinated by an iminophosphine ligand was found to catalyze the addition of alkynylstannanes to a carbon-carbon triple bond of various alkynes in moderate to good yields with exclusive syn selectivity. The alkynyl group in the stannanes was attached: mainly to the internal carbon of terminal alkynes, except for 1-alkyn-3-ones and alkynoates, where the alkynyl group was connected to the terminal carbon. Steric bulk of the ligand markedly influenced on the regioselectivity and reaction rate: an iminophosphine with a bulkier imino moiety accelerated the alkynylstannylation with higher regioselectivity. On the basis of these observations, the. mechanism of the present reaction is discussed.

  DOI：

  10.1021/om000828u

文献信息

• The palladium–iminophosphine catalyst for the reactions of organostannanes
  作者：Eiji Shirakawa、Tamejiro Hiyama

  DOI：10.1016/s0022-328x(98)01056-0

  日期：1999.3

  organostannanes with aryl halides. The mechanistic studies show that the reaction of an alkynylstannane proceeds through an unprecedented catalytic cycle which involves an oxidative addition of the organostannane to the Pd(0)–iminophosphine complex. The catalyst was demonstrated to be also useful for the carbostannylation of alkynes and the homocoupling reaction of organostannanes.

  发现由亚氨基膦配体配位的钯配合物是有机锡与芳基卤化物偶联的显着活性催化剂。机理研究表明，炔基锡烷的反应是通过前所未有的催化循环进行的，该循环涉及将有机锡烷氧化加成到Pd（0）-亚氨基膦配合物中。已证明该催化剂也可用于炔烃的羰基合成和有机锡的均偶联反应。
• Palladium−Iminophosphine-Catalyzed Alkynylstannylation of Alkynes
  作者：Hiroto Yoshida、Eiji Shirakawa、Takuya Kurahashi、Yoshiaki Nakao、Tamejiro Hiyama

  DOI：10.1021/om000828u

  日期：2000.12.1

  A palladium complex coordinated by an iminophosphine ligand was found to catalyze the addition of alkynylstannanes to a carbon-carbon triple bond of various alkynes in moderate to good yields with exclusive syn selectivity. The alkynyl group in the stannanes was attached: mainly to the internal carbon of terminal alkynes, except for 1-alkyn-3-ones and alkynoates, where the alkynyl group was connected to the terminal carbon. Steric bulk of the ligand markedly influenced on the regioselectivity and reaction rate: an iminophosphine with a bulkier imino moiety accelerated the alkynylstannylation with higher regioselectivity. On the basis of these observations, the. mechanism of the present reaction is discussed.