methyl (3Z,7S,8S,9E,11E)-7,8-dimethyl-13-oxo-8-(phenylmethoxymethyl)-11-tri(propan-2-yl)silyloxy-1-oxacyclotrideca-3,9,11-triene-4-carboxylate | 1365268-23-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: methyl (3Z,7S,8S,9E,11E)-7,8-dimethyl-13-oxo-8-(phenylmethoxymethyl)-11-tri(propan-2-yl)silyloxy-1-oxacyclotrideca-3,9,11-triene-4-carboxylate
• CAS: 1365268-23-0
• 化学式: C₃₃H₅₀O₆Si
• 分子量: 570.842
• InChiKey: MOTNBFBFMKVDQP-AVXFLRMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.91
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (3Z,7S,8S,9E,11E)-7,8-dimethyl-13-oxo-8-(phenylmethoxymethyl)-11-tri(propan-2-yl)silyloxy-1-oxacyclotrideca-3,9,11-triene-4-carboxylate 在 2,6-二叔丁基-4-甲基苯酚 、 四丁基氟化铵 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 四氢呋喃 为溶剂， 反应 34.0h， 以56%的产率得到methyl (3aR,5aR,6S,7S,9aR,9bS)-6,7-dimethyl-3,4-dioxo-6-(phenylmethoxymethyl)-1,3a,5,5a,7,8,9,9b-octahydrobenzo[e][2]benzofuran-9a-carboxylate
  参考文献：
  名称：

  Synthetic studies on (+)-bucidarasin C: two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

  摘要：

  This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.058
• 作为产物：
  描述：

  methyl (2Z,5S,6S,7E)-6-((benzyloxy)methyl)-2-(2-((tert-butyldiphenylsilyl)oxy)ethylidene)-8-(1,3-dioxan-2-yl)-5,6-dimethyloct-7-enoate 在 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 pig liver esterase 、 2-甲基-2-丁烯 、 pyridine hydrofluoride 、 2-甲基-6-硝基苯甲酸酐 、 水 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 二甲基亚砜 、 1,2-二氯乙烷 、 叔丁醇 、 苯 为溶剂， 反应 17.0h， 生成 methyl (3Z,7S,8S,9E,11E)-7,8-dimethyl-13-oxo-8-(phenylmethoxymethyl)-11-tri(propan-2-yl)silyloxy-1-oxacyclotrideca-3,9,11-triene-4-carboxylate
  参考文献：
  名称：

  Synthetic studies on (+)-bucidarasin C: two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity

  摘要：

  This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.01.058

文献信息

• Synthetic studies on (+)-bucidarasin C: two diastereoselective transannular reactions producing cis-decaline derivatives that show reversal selectivity
  作者：Akinobu Nakahara、Misaki Kanbe、Masahisa Nakada

  DOI：10.1016/j.tetlet.2012.01.058

  日期：2012.3

  This manuscript describes studies on the construction of the cis-decaline core of (+)-bucidarasin C. The transannular Diels-Alder (TADA) reaction of a macrocyclic lactone successfully afforded the desired cis-decaline derivative in a stereoselective manner. On the other hand, the stereoselective transannular cascade Michael (TACM) reaction of the parent macrocyclic lactone afforded the diastereomeric cis-decaline derivative as the major product. (C) 2012 Elsevier Ltd. All rights reserved.