(2'S,4(1)'R,7a'S,10a'R)-2'-methyl-1,5,5',6',7a',8',10',10a'-octahydrospiro[benzo[e][1,3]dioxepine-3,9'-benzofuro[4-b][1,4]dioxin]-3'(2'H)-one | 1159795-96-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2'S,4(1)'R,7a'S,10a'R)-2'-methyl-1,5,5',6',7a',8',10',10a'-octahydrospiro[benzo[e][1,3]dioxepine-3,9'-benzofuro[4-b][1,4]dioxin]-3'(2'H)-one
• 英文别名: (3'S,4'aR,7'aS,10'aR)-3'-methylspiro[1,5-dihydro-2,4-benzodioxepine-3,6'-4a,5,7,7a,9,10-hexahydro-[1,4]dioxino[2,3-d][1]benzofuran]-2'-one
• CAS: 1159795-96-6
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: CRNOCDQJYVOKLN-NALNUFGESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2'S,4(1)'R,7a'S,10a'R)-2'-methyl-1,5,5',6',7a',8',10',10a'-octahydrospiro[benzo[e][1,3]dioxepine-3,9'-benzofuro[4-b][1,4]dioxin]-3'(2'H)-one 在 二异丁基氢化铝 、 水 、 rochelle salt 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 1.75h， 生成
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k
• 作为产物：
  描述：

  (2S,4(1)R,7aS,10R,10aS)-2-methyltetrahydro-2H-benzofuro[4-b][1,4]dioxin-3,9(10H,10aH)-dione 、 邻苯二甲醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 24.0h， 以85%的产率得到(2'S,4(1)'R,7a'S,10a'R)-2'-methyl-1,5,5',6',7a',8',10',10a'-octahydrospiro[benzo[e][1,3]dioxepine-3,9'-benzofuro[4-b][1,4]dioxin]-3'(2'H)-one
  参考文献：
  名称：

  Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments

  摘要：

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.

  DOI：

  10.1021/jo900401k

文献信息

• Enantioselective Total Synthesis of All of the Known Chiral Cleroindicins (C−F): Clarification Among Optical Rotations and Assignments
  作者：Todd A. Wenderski、Shenlin Huang、Thomas R. R. Pettus

  DOI：10.1021/jo900401k

  日期：2009.6.5

  Enantioselective syntheses of all of the named chiral members of the cleroindicin family (C-F) are reported. This effort demonstrates the synthetic utility of a 2,4-dihydroxybenzaldehyde as a starting material for natural product synthesis through the use sequential o-quinone methide chemistry and diastereoselective dearomatization. Natural cleroindicin F was shown to be nearly racemic, and an optically pure synthetic sample of cleroindicin F was found to racemize under slightly basic conditions. All other natural chiral cleroindicins are shown to be partially racemic.