methyl 5-methyl-4-oxo-2-(2-trimehylsilylethynylbenzyl)hexanoate | 224568-48-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: methyl 5-methyl-4-oxo-2-(2-trimehylsilylethynylbenzyl)hexanoate
• 英文别名: Methyl 5-methyl-4-oxo-2-[[2-(2-trimethylsilylethynyl)phenyl]methyl]hexanoate
• CAS: 224568-48-3
• 化学式: C₂₀H₂₈O₃Si
• 分子量: 344.526
• InChiKey: MPTFQBUCINIQRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.86
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-methyl-4-oxo-2-(2-trimehylsilylethynylbenzyl)hexanoate 在 六甲基磷酰三胺 、 tin(II) iodide 、 四丁基氟化铵 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 methyl 8-hydroxy-8-isopropyl-5,6,7,8-tetrahydrobenzocyclooctene-6-carboxylate
  参考文献：
  名称：

  Competition between Novel 8- endo-dig and 6- trig Cyclizations of Samarium Ketyls Leading either to Benzannulated Cyclooctene or to Hexahydronaphthalene Derivatives

  摘要：

  Ketoesters 3a-3h with an alkynylaryl substituent were prepared by standard methods starting from siloxycyclopropanes 6a and 6b. Their reactions with 2.2 equiv. of samarium diiodide in the presence of hexamethyl phosphoramide either produced benzannulated cyclooctenol derivatives 4b (or lactone 9), 4f, 4g, and 4h or hexahydronaphthalene derivatives 5a, 5c, and 5d. The competition between 8-endo-dig and 6-trig cyclizations strongly depends on the substitution pattern of 3. Plausible explanations for this competition and of the diastereoselectivity observed are presented in this paper. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00353-7
• 作为产物：
  描述：

  methyl 1-(2-iodobenzyl)-2-isopropyl-2-trimethylsiloxycycloprpanecarboxylate 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 triethylamine tris(hydrogen fluoride) 、 二乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 methyl 5-methyl-4-oxo-2-(2-trimehylsilylethynylbenzyl)hexanoate
  参考文献：
  名称：

  Competition between Novel 8- endo-dig and 6- trig Cyclizations of Samarium Ketyls Leading either to Benzannulated Cyclooctene or to Hexahydronaphthalene Derivatives

  摘要：

  Ketoesters 3a-3h with an alkynylaryl substituent were prepared by standard methods starting from siloxycyclopropanes 6a and 6b. Their reactions with 2.2 equiv. of samarium diiodide in the presence of hexamethyl phosphoramide either produced benzannulated cyclooctenol derivatives 4b (or lactone 9), 4f, 4g, and 4h or hexahydronaphthalene derivatives 5a, 5c, and 5d. The competition between 8-endo-dig and 6-trig cyclizations strongly depends on the substitution pattern of 3. Plausible explanations for this competition and of the diastereoselectivity observed are presented in this paper. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00353-7

文献信息

• Competition between Novel 8- endo-dig and 6- trig Cyclizations of Samarium Ketyls Leading either to Benzannulated Cyclooctene or to Hexahydronaphthalene Derivatives
  作者：Erathodiyil Nandanan、Chimmanamada U Dinesh、Hans-Ulrich Reissig

  DOI：10.1016/s0040-4020(00)00353-7

  日期：2000.6

  Ketoesters 3a-3h with an alkynylaryl substituent were prepared by standard methods starting from siloxycyclopropanes 6a and 6b. Their reactions with 2.2 equiv. of samarium diiodide in the presence of hexamethyl phosphoramide either produced benzannulated cyclooctenol derivatives 4b (or lactone 9), 4f, 4g, and 4h or hexahydronaphthalene derivatives 5a, 5c, and 5d. The competition between 8-endo-dig and 6-trig cyclizations strongly depends on the substitution pattern of 3. Plausible explanations for this competition and of the diastereoselectivity observed are presented in this paper. (C) 2000 Elsevier Science Ltd. All rights reserved.