(8R,8aR,4bS,13aS)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3-trimethoxy-11,12-methylenedioxy-7-oxa-tribenzo[a,c,e]cyclo-heptene-6-carboxylic acid methyl ester | 1296671-44-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: (8R,8aR,4bS,13aS)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3-trimethoxy-11,12-methylenedioxy-7-oxa-tribenzo[a,c,e]cyclo-heptene-6-carboxylic acid methyl ester
• 英文别名: methyl (8S,12R,13R)-12-[(4R)-4-ethyl-2-oxo-1,3-oxazolidin-3-yl]-3,4,5-trimethoxy-11,18,20-trioxapentacyclo[13.7.0.02,7.08,13.017,21]docosa-1(22),2,4,6,9,15,17(21)-heptaene-10-carboxylate
• CAS: 1296671-44-7
• 化学式: C₂₉H₃₁NO₁₀
• 分子量: 553.566
• InChiKey: HASRWTPTXTZWEN-SRTTXIJCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  111
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3,4-methylenedioxy-trans-cinnamic acid 在 lithium aluminium tetrahydride 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 thallium (III) oxide 、 三氟甲磺酸 、 三氟甲磺酸酐 、 三氟化硼乙醚 、 对甲苯磺酸 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 甲苯 为溶剂， 反应 175.5h， 生成 (8R,8aR,4bS,13aS)-8-((R)-4-ethyl-2-oxo-oxazolidin-3-yl)-4b,8,8a,9-tetrahydro-1,2,3-trimethoxy-11,12-methylenedioxy-7-oxa-tribenzo[a,c,e]cyclo-heptene-6-carboxylic acid methyl ester
  参考文献：
  名称：

  New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin

  摘要：

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.097

文献信息

• New two-step sequence involving a hetero-Diels–Alder and a nonphenolic oxidative coupling reaction: a convergent access to analogs of steganacin
  作者：Mathieu Y. Laurent、Vivien Stocker、Valéry Momo Temgoua、Gilles Dujardin、Robert Dhal

  DOI：10.1016/j.tetlet.2011.01.097

  日期：2011.4

  A new family of analogs of steganacin, an important antimitotic compound, was accessed. It takes advantage of a completely stereoselective sequence of two key steps. The central dihydropyrane core is built by a highly diastereoselective and facially controlled hetero-Diels-Alder reaction. It is followed by a nonphenolic biaryl oxidative coupling with a complete atropo-stereoselectivity. It leads to a quick way to form cyclic biaryl lignans. (C) 2011 Elsevier Ltd. All rights reserved.