(Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylbut-2-enal | 877833-42-6

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylbut-2-enal
• CAS: 877833-42-6
• 化学式: C₂₁H₂₆O₂Si
• 分子量: 338.522
• InChiKey: BQOBGPCJZKVDBH-SDXDJHTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylbut-2-enal 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 n-BuBOTf 、 4-甲基苯磺酸吡啶 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 100.33h， 生成 6-Allyl-2-[3-(tert-Butyldiphenylsilanyloxy)-2-methylpropenyl]-3-methyl-4-triethylsilanyloxytetrahydropyran
  参考文献：
  名称：

  An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence

  摘要：

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.11.156
• 作为产物：
  描述：

  methyl 4-(tert-butyldiphenylsilyloxy)-2-butynoate 在 copper(l) iodide 、 四丙基高钌酸铵 、 diisobutylaluminum hydride 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 (Z)-4-[tert-butyl(diphenyl)silyl]oxy-3-methylbut-2-enal
  参考文献：
  名称：

  An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence

  摘要：

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2005.11.156

文献信息

• Alkyne-Enol Ether Cross-Metathesis in the Presence of CuSO₄: Direct Formation of 3-Substituted Crotonaldehydes in Aqueous Medium
  作者：Daniele Castagnolo、Lorenzo Botta、Maurizio Botta

  DOI：10.1021/jo900205x

  日期：2009.4.17

  An efficient synthesis of 3-substituted crotonaldehydes via alkyne-enol ether cross-metathesis in the presence of CuSO4 and in aqueous medium was developed. Crotonaldehydes were obtained in good yields from terminal aryl-alkynes as well as from terminal alkyl-alkynes. All of the reactions were carried out under microwave irradiation and were completed in a few minutes. Water was used as the cosolvent, making c, this approach safer, economic, and desiderable from an enviromental point of view.
• An efficient synthesis of the C1–C14 subunit of (−)-lasonolide A via a target oriented β-C-glycoside formation sequence
  作者：Kailas B. Sawant、Fei Ding、Michael P. Jennings

  DOI：10.1016/j.tetlet.2005.11.156

  日期：2006.2

  An efficient synthesis of the C-1-C-14 Subunit resident in (-)-lasonolide A is reported herein. The key reaction features that were utilized include a Molander-Reformatsky SmI2 mediated intramolecular aldol reaction followed by a diastereoselective target oriented beta-C-glycoside formation sequence. Lastly, a chemo- and diastereoselective cross-metathesis of a terminal olefin in the presence of a trisubstituted alkene with acrolein and subsequent olefination of the aldehyde moiety allowed for the completion of the (E,E)-diene side chain. (c) 2005 Published by Elsevier Ltd.