tributyl(cyclohexyl(methoxymethoxy)methyl)stannane | 113248-99-0

• 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: tributyl(cyclohexyl(methoxymethoxy)methyl)stannane
• 英文别名: Tributyl[cyclohexyl(methoxymethoxy)methyl]stannane；tributyl-[cyclohexyl(methoxymethoxy)methyl]stannane
• CAS: 113248-99-0
• 化学式: C₂₁H₄₄O₂Sn
• 分子量: 447.289
• InChiKey: ROBRWFMPYXEJEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.94
• 重原子数：
  24
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tributyl(cyclohexyl(methoxymethoxy)methyl)stannane 在 正丁基锂 、 高氯酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 5-cyclohexyldihydrofuran-2(3H)-one
  参考文献：
  名称：

  An expeditious enantioselective synthesis of γ-lactones

  摘要：

  DOI：

  10.1016/s0040-4039(00)88894-2
• 作为产物：
  描述：

  三正丁基氢锡 、 环己烷基甲醛 在 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 tributyl(cyclohexyl(methoxymethoxy)methyl)stannane
  参考文献：
  名称：

  Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy

  摘要：

  We designed and synthesized perhexiline analogues that have the same therapeutic profile as the parent cardiovascular drug but lacking its metabolic liability associated with CYP2D6 metabolism. Cycloalkyl perhexiline analogues 6a-j were found to be unsuitable for further development, as they retained a pharmacokinetic profile very similar to that shown by the parent compound. Multistep synthesis of perhexiline analogues incorporating fluorine atoms onto the cyclohexyl ring(s) provided a range of different fluoroperhexiline analogues. Of these, analogues 50 (4,4-gem-difluoro) and 62 (4,4,4',4'-tetrafluoro) were highly stable and showed greatly reduced susceptibility to CYP2D6-mediated metabolism. In vitro efficacy studies demonstrated that a number of derivatives retained acceptable potency against CPT-1. Having the best balance of properties, 50 was selected for further evaluation. Like perhexiline, it was shown to be selectively concentrated in the myocardium and, using the Langendorff model, to be effective in improving both cardiac contractility and relaxation when challenged with high fat buffer.

  DOI：

  10.1021/acs.jmedchem.6b01592

文献信息

• Applications of α-alkoxyorganocuprate reagents in the regiospecific synthesis of cyclic homoaldol products
  作者：Russell J. Linderman、Alex Godfrey、Kelly Horne

  DOI：10.1016/0040-4020(89)80077-8

  日期：1989.1

  Cyclic homoaldol products have been prepared via conjugate addition of α-alkoxyorganocuprate reagents to enones. The reactions are regiospecific, providing the homoaldol products in good to excellent yields. The preparation of the cuprates from the α-alkoxyorganostannane precursor is described in detail. Best results were obtained with the higher order cyano cuprate reagent using in-situ trimethylsilyl

  通过将α-烷氧基有机辛酸酯试剂共轭添加到烯酮中，已经制备了环状同醛醇产物。该反应是区域特异性的，提供高至优异产率的均醛醇产物。详细描述了由α-烷氧基有机锡链烷烃前体制备铜酸盐。使用原位三甲基甲硅烷基氯的高阶氰基铜酸盐试剂可获得最佳结果。
• A reactivity umpolung route to cyclic homoenolate aldol products α-alkoxyorganocuprate conjugate additions
  作者：Russell J. Linderman、Alex Godfrey、Kelly Horne

  DOI：10.1016/s0040-4039(00)96418-9

  日期：1987.1
• LINDERMAN, RUSSELL J.;GODFREY, ALEX;HORNE, KELLY, TETRAHEDRON, 45,(1989) N, C. 495-506
  作者：LINDERMAN, RUSSELL J.、GODFREY, ALEX、HORNE, KELLY

  DOI：——

  日期：——
• LINDERMAN, RUSSELL J.;GODFREY, ALEX;HORNE, KELLY, TETRAHEDRON LETT., 28,(1987) N 34, 3911-3914
  作者：LINDERMAN, RUSSELL J.、GODFREY, ALEX、HORNE, KELLY

  DOI：——

  日期：——
• Development of Fluorinated Analogues of Perhexiline with Improved Pharmacokinetic Properties and Retained Efficacy
  作者：Chih-Chung Tseng、Hannah Noordali、Monica Sani、Melanie Madhani、Denis M. Grant、Michael P. Frenneaux、Matteo Zanda、Iain R. Greig

  DOI：10.1021/acs.jmedchem.6b01592

  日期：2017.4.13

  We designed and synthesized perhexiline analogues that have the same therapeutic profile as the parent cardiovascular drug but lacking its metabolic liability associated with CYP2D6 metabolism. Cycloalkyl perhexiline analogues 6a-j were found to be unsuitable for further development, as they retained a pharmacokinetic profile very similar to that shown by the parent compound. Multistep synthesis of perhexiline analogues incorporating fluorine atoms onto the cyclohexyl ring(s) provided a range of different fluoroperhexiline analogues. Of these, analogues 50 (4,4-gem-difluoro) and 62 (4,4,4',4'-tetrafluoro) were highly stable and showed greatly reduced susceptibility to CYP2D6-mediated metabolism. In vitro efficacy studies demonstrated that a number of derivatives retained acceptable potency against CPT-1. Having the best balance of properties, 50 was selected for further evaluation. Like perhexiline, it was shown to be selectively concentrated in the myocardium and, using the Langendorff model, to be effective in improving both cardiac contractility and relaxation when challenged with high fat buffer.