pent-2-enyl-tributylstannane | 182260-08-8

• 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: pent-2-enyl-tributylstannane
• 英文别名: pent-2-enyltributyltin；tributyl(pent-2-en-1-yl)stannane；tributyl-(2-pentenyl)tin；tributyl(pent-2-enyl)stannane
• CAS: 182260-08-8
• 化学式: C₁₇H₃₆Sn
• 分子量: 359.183
• InChiKey: KJBPWBBUAJFNAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  18.0
• 可旋转键数：
  12.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  碘甲基膦酸二乙酯 、 pent-2-enyl-tributylstannane 在 indium(III) chloride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以59%的产率得到diethyl 2-ethylbut-3-en-1-ylphosphonate
  参考文献：
  名称：

  Indium(III) Halide-Catalyzed UV-Irradiated Radical Coupling of Iodomethylphosphorus Compounds with Various Organostannanes

  摘要：

  The first catalytic radical coupling of iodomethylphosphorus compounds was accomplished with allyl-, alkenyl-, and allenylstannanes under UV Irradiation in the presence of an indium(III) halide catalyst, for which a transmetalated allylic indium species was confirmed lobe an active radical species.

  DOI：

  10.1021/ol4005257
• 作为产物：
  描述：

  2,4,6-三异丙基苯磺酰基肼 、 tributyl(2,4-pentadienyl)stannane 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醚 为溶剂， 生成 pent-2-enyl-tributylstannane
  参考文献：
  名称：

  An Easy Access to Stereodefined 2-Pentenyltins by Partial Hydrogenation of 2,4-Pentadienyltins with Diazene

  摘要：

  通过氢化三丁基-(2,4-戊二烯基)锡与由 2,4,6-三异丙基苯磺酰肼生成的重氮，很容易制备出高产率的三丁基-(2-戊烯基)锡。在共轭二烯体系中，末端双键被选择性氢化。内部双键的立体化学结构完全保留。

  DOI：

  10.1246/bcsj.67.274

文献信息

• A highly stereospecific allylation of benzil by using (E)-and (Z)-allylic stannanes via photoinduced electron transfer
  作者：Akio Takuwa、Yutaka Nishigaichi、Takashi Yamaoka、Kenji Lihama

  DOI：10.1039/c39910001359

  日期：——

  Irradiation of benzil in acetonitrile in the presence of (E)- and (Z)-but-2-enyl-, pent-2-enyl-, and hex-2-enyl-tributylstannanes afforded the corresponding (E)- and (Z)-homcallylic alcohols, respectively, with complete retention of the original double bond configuration in good yields.

  在(E)-和(Z)-丁-2-烯基、戊-2-烯基和己-2-烯基三丁基锡烷存在下，在乙腈中辐照苯偶姻，可分别得到相应的(E)-和(Z)-高烯丙基醇，并以良好的收率完全保留了原始双键构型。
• 2-Arylpropionic CXC Chemokine Receptor 1 (CXCR1) Ligands as Novel Noncompetitive CXCL8 Inhibitors
  作者：Marcello Allegretti、Riccardo Bertini、Maria Candida Cesta、Cinzia Bizzarri、Rosa Di Bitondo、Vito Di Cioccio、Emanuela Galliera、Valerio Berdini、Alessandra Topai、Giuseppe Zampella、Vincenzo Russo、Nicoletta Di Bello、Giuseppe Nano、Luca Nicolini、Massimo Locati、Piercarlo Fantucci、Saverio Florio、Francesco Colotta

  DOI：10.1021/jm049082i

  日期：2005.6.1

  The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCL8-induced human PMNS chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.