(Z)-1-[4-(2-(tributylstannyl)vinyl)phenyl]but-3-en-1-ol | 1599432-64-0

• 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-[4-(2-(tributylstannyl)vinyl)phenyl]but-3-en-1-ol
• 英文别名: 1-[4-[(Z)-2-tributylstannylethenyl]phenyl]but-3-en-1-ol
• CAS: 1599432-64-0
• 化学式: C₂₄H₄₀OSn
• 分子量: 463.291
• InChiKey: KTJNIRCTGXTHSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.22
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-乙炔基苯甲醛 在 三氟化硼乙醚 、 三(五氟苯基)硼烷 作用下， 以 甲苯 为溶剂， 反应 2.25h， 生成 (Z)-1-[4-(2-(tributylstannyl)vinyl)phenyl]but-3-en-1-ol 、 (E)-1-[4-(2-(tributylstannyl)vinyl)phenyl]but-3-en-1-ol
  参考文献：
  名称：

  A One-Pot Allylation–Hydrostannation Sequence with Recycling of the Intermediate Tin Waste

  摘要：

  A one-pot allylation and hydrostannation of alkynals where the tin byproduct formed in the first step of the reaction is recycled and used in the second step of the sequence is presented. Specifically, a BF3 center dot OEt2-promoted allylstannation of the aldehyde moiety in the alkynalis followed by the introduction of polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)(3), which convert the tin byproduct of the allylation into Bu3SnH, which then hydrostannates the alkyne in the molecule. Sn-119 and B-11 NMR data suggest an organotin fluoride species is formed during the allylation step and involved in the tin recycling step.

  DOI：

  10.1021/ol500460u

文献信息

• A One-Pot Allylation–Hydrostannation Sequence with Recycling of the Intermediate Tin Waste
  作者：Banibrata Ghosh、Maria Del Rosario I. Amado-Sierra、Daniel Holmes、Robert E. Maleczka

  DOI：10.1021/ol500460u

  日期：2014.5.2

  A one-pot allylation and hydrostannation of alkynals where the tin byproduct formed in the first step of the reaction is recycled and used in the second step of the sequence is presented. Specifically, a BF3 center dot OEt2-promoted allylstannation of the aldehyde moiety in the alkynalis followed by the introduction of polymethylhydrosiloxane (PMHS) and catalytic B(C6F5)(3), which convert the tin byproduct of the allylation into Bu3SnH, which then hydrostannates the alkyne in the molecule. Sn-119 and B-11 NMR data suggest an organotin fluoride species is formed during the allylation step and involved in the tin recycling step.