3-(tributylstannyl)but-3-en-1-ol | 122229-78-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机过渡后金属化合物
• 英文名称: 3-(tributylstannyl)but-3-en-1-ol
• 英文别名: 2-tributylstannyl-4-hydroxybut-1-ene
• CAS: 122229-78-1
• 化学式: C₁₆H₃₄OSn
• 分子量: 361.155
• InChiKey: UAXAHSXCWADQQE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.31
• 重原子数：
  18
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,6,6-trimethylcyclohex-1-en-1-yl trifluoromethanesulfonate 、 3-(tributylstannyl)but-3-en-1-ol 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 三苯胂 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 16.0h， 以51%的产率得到3-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-1-ol
  参考文献：
  名称：

  Stereocontrolled Synthesis of 6-s-cis- and 6-s-trans-Locked 9Z-Retinoids by Hydroxyl-Accelerated Stille Coupling of (Z)-Tri-n-Butylstannylbut-2-en-1-ol and Bicyclic Dienyl Triflates

  摘要：

  Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 degrees C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.

  DOI：

  10.1021/jo9917588
• 作为产物：
  描述：

  (E)-4-[dimethyl(phenyl)silyl]-3-tributylstannylbut-3-en-1-ol 、 四丁基氟化铵 以31%的产率得到
  参考文献：
  名称：

  RITTER, KURT, SYNTHESIS (BRD),(1989) N, C. 218-221

  摘要：

  DOI：
• 作为试剂：
  描述：

  (E)-4-(tributylstannyl)but-3-en-1-ol 、 diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate 在 双(乙腈)氯化钯(II) lithium bromide 、 3-(tributylstannyl)but-3-en-1-ol 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以30%的产率得到diphenylmethyl 7β-formamido-3-[(E)-4-hydroxy-1-buten-1-yl]-3-cephem-4-carboxylate
  参考文献：
  名称：

  口服活性头孢菌素：3-[（E）和（Z）-2-取代的乙烯基]-头孢菌素的合成，构效关系和口服吸收。

  摘要：

  一系列7β-[（Z）-2-（2-氨基噻唑-4-基）-2-羟基亚氨基乙酰胺基o] -3-[（E）-和（Z）-2-取代的乙烯基] -3- Cephem-使用3-甲磺酰氧基-3-cephem的钯催化偶联反应和E取代的乙烯基锡烷的钯催化偶联反应或3-triphenylphosphoniummethyl cephem和醛的Wittig反应设计和合成4-羧酸是关键步骤。评价这些化合物在大鼠中的体外抗菌活性和口服吸收。他们中的许多人对革兰氏阳性和革兰氏阴性细菌（包括流感嗜血杆菌）均表现出出色的抗菌活性。其中，FR86524（2j）。在C-3位置具有（Z）-2-（3-吡啶基）乙烯基部分的化合物具有最佳平衡的活性。尽管FR86254口服吸收率低，

  DOI：

  10.1016/s0968-0896(99)00257-6

文献信息

• The Total Synthesis of (±)-11-<i>O</i>-Debenzoyltashironin
  作者：Silas P. Cook、Alessandra Polara、Samuel J. Danishefsky

  DOI：10.1021/ja0670254

  日期：2006.12.1

  The total synthesis of the putative non-peptidyl neurotrophic factor 11-O-debenzoyltashironin has been accomplished. The key transformation involves a biomimetic oxidative dearomatization/transannular Diels-Alder sequence that closes the tetracyclic carbon skeleton present in the natural product.
• Miyake, Hideyoshi; Yamamura, Kimiaki, Chemistry Letters, 1989, p. 981 - 984
  作者：Miyake, Hideyoshi、Yamamura, Kimiaki

  DOI：——

  日期：——
• RITTER, KURT, SYNTHESIS (BRD),(1989) N, C. 218-221
  作者：RITTER, KURT

  DOI：——

  日期：——
• Stereocontrolled Synthesis of 6-<i>s</i>-<i>cis</i>- and 6-<i>s</i>-<i>trans</i>-Locked 9<i>Z</i>-Retinoids by Hydroxyl-Accelerated Stille Coupling of (<i>Z</i>)-Tri-<i>n</i>-Butylstannylbut-2-en-1-ol and Bicyclic Dienyl Triflates
  作者：Beatriz Domínguez、Yolanda Pazos、Angel R. de Lera

  DOI：10.1021/jo9917588

  日期：2000.9.1

  Analogues of 9-cis-retinoic acid with locked 6-s-cis and 6-s-trans conformations have been stereoselectively synthesized using a Stille coupling reaction between bicyclic dienyl triflates (5 and 6, respectively) and (Z)-tributylstannylbut-2-en-1-ol (7) to stablish the Z geometry of the polyenic side chain. The mild conditions (25 degrees C, 30 min) of this coupling stand in contrast to the reluctance of the isomeric (E)-tributylstannylbut-2-en-1-ol (18) to react with triflates 5/6. The significant rate differences experimentally observed in Stille reactions between isomeric (Z)- and (E)-tri-n-butylstannylalkenols in favor of the former isomer, even with highly hindered alkenyl triflates, is ascribed to internal coordination of palladium to the heteroatom in the presumably rate-limiting transmetalation step. Dienals and trienals with an E geometry, which are not efficiently available by direct coupling of the corresponding triflates and E-stannanes, can in turn be obtained by isomerization of their Z-isomers.