methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]bicyclo[3.2.1]oct-6-ene-6-carboxylate | 1309659-97-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]bicyclo[3.2.1]oct-6-ene-6-carboxylate
• 英文别名: methyl (1S,2R,5R)-8-(methoxymethylidene)-5-methyl-2-propan-2-yl-7-(trifluoromethylsulfonyloxy)bicyclo[3.2.1]oct-6-ene-6-carboxylate
• CAS: 1309659-97-9
• 化学式: C₁₇H₂₃F₃O₆S
• 分子量: 412.427
• InChiKey: LPROIFBVZNSKGW-RSAASHCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]bicyclo[3.2.1]oct-6-ene-6-carboxylate 在 四(三苯基膦)钯 、 三正丁胺 、 二异丁基氢化铝 、 lithium chloride 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 4.75h， 生成 (1S,7S,10R)-11-(methoxymethylene)-7-methyl-10-(methylethyl)-4-oxatricyclo[5.3.1.0(2,6)]undec-2(6)-en-3-one
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007
• 作为产物：
  描述：

  (1S,4R,5S)-8-(methoxymethylene)-1-methyl-4-(methylethyl)bicyclo[3.2.1]octan-6-one 在 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 2.5h， 生成 methyl (1S,2R,5R)-8-(methoxymethylene)-5-methyl-2-(methylethyl)-7-[(trifluoromethyl)sulfonyloxy]bicyclo[3.2.1]oct-6-ene-6-carboxylate
  参考文献：
  名称：

  First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B

  摘要：

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.04.007

文献信息

• First total syntheses of bicyclic marine sesquiterpenoids drechslerines A and B
  作者：Hisahiro Hagiwara、Masakazu Fukushima、Kimihiko Kinugawa、Takuya Matsui、Takashi Hoshi、Toshio Suzuki

  DOI：10.1016/j.tet.2011.04.007

  日期：2011.6

  The first total syntheses of the bicyclic sesquiterpenoids drechslerines A (1) and B (2), which were isolated from the algicolous fungus Drechslera dematioidea in the marine red alga Liagora viscida, has been accomplished starting from (S)-carvone (13) via three palladium-catalyzed reactions, namely, diastereoselective allylation, conjugate reduction, and carbon monoxide insertion, as the key reactions. (C) 2011 Elsevier Ltd. All rights reserved.