(S)-N-(5,6,7,11a-tetrahydro-1,2,3-trimethoxy-11-ethoxycarbonyl benzo[a]heptaleno[7,8-b]furan-10-one-7-yl) acetamide | 196711-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环七呋喃
• 英文名称: (S)-N-(5,6,7,11a-tetrahydro-1,2,3-trimethoxy-11-ethoxycarbonyl benzo[a]heptaleno[7,8-b]furan-10-one-7-yl) acetamide
• 英文别名: ethyl (10S)-10-acetamido-3,4,5-trimethoxy-15-oxo-14-oxatetracyclo[9.8.0.02,7.013,17]nonadeca-1(11),2,4,6,12,16,18-heptaene-16-carboxylate
• CAS: 196711-86-1
• 化学式: C₂₆H₂₇NO₈
• 分子量: 481.502
• InChiKey: XSNJWKITGSPVST-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (E)-2-methyl-4-phenyl-1,3-butadiene 、 (S)-N-(5,6,7,11a-tetrahydro-1,2,3-trimethoxy-11-ethoxycarbonyl benzo[a]heptaleno[7,8-b]furan-10-one-7-yl) acetamide 以 xylene 为溶剂， 反应 36.0h， 以55%的产率得到ethyl (10S)-10-acetamido-3,4,5-trimethoxy-15-methyl-15-[(E)-2-phenylethenyl]tetracyclo[9.8.0.02,7.013,17]nonadeca-1(11),2,4,6,12,16,18-heptaene-16-carboxylate
  参考文献：
  名称：

  2-氧代-2H-环庚[b]呋喃衍生物与二烯和亲二烯物的环加成反应

  摘要：

  描述了分别以8π和4π组分参与的2-oxo-2H-cyclohepta [b]呋喃衍生物对不同的二烯和双亲物的环加成反应。观察到的反应性和选择性是通过AM1计算合理化的。

  DOI：

  10.1016/s0040-4020(99)00100-3
• 作为产物：
  描述：

  秋水仙碱 、 丙二酸二乙酯 在 sodium 作用下， 以 乙醚 、 苯 为溶剂， 反应 14.0h， 以60%的产率得到(S)-N-(5,6,7,11a-tetrahydro-1,2,3-trimethoxy-11-ethoxycarbonyl benzo[a]heptaleno[7,8-b]furan-10-one-7-yl) acetamide
  参考文献：
  名称：

  [8 + 2] 2H-环庚基[b]呋喃-2-酮与无环1,3-二烯的环加成反应：通往新型双环[5.3.0]环系的简便方法

  摘要：

  描述了3-乙氧基羰基2H-环庚[b]呋喃-2-酮与无环1,3-二烯的新型[8 + 2]环加成反应。还研究了该方法在结合双环[5.3.0]环系统的修饰类秋水仙碱合成中的潜在应用。©1997爱思唯尔科学有限公司。

  DOI：

  10.1016/s0040-4039(97)01472-x

文献信息

• Synthesis of 1-Oxaazulan-2-ones and Furanotropones from Troponoids: a Reexamination and Extension to Colchicinoids
  作者：Marino Cavazza、Graziano Guella、Francesco Pietra

  DOI：10.1016/s0040-4020(00)00106-x

  日期：2000.3

  Reactions of [3,5,7-H-2(3)]-2-tosyloxytropone (1b) in DMSO with enolates that, like sodium ethyl acetoacetate or sodium diethyl malonate, bear a leaving group, occur at C-7, followed by either sequential protonation at C-2, 1,6-elimination, and intramolecular heterocyclization (to give 1-oxaazulan-2-ones), or sequential sulfinate loss and intramolecular heterocyclization (to give furanotropones). The latter is the exclusive route with enolates that, like sodium acetylacetonate, do not bear a leaving group. 9-Tosyloxyisocolchicide (15) behaves like 2-tosyloxytropone, giving the product 16 of C-11 attack, whereas 10-tosyloxycolchicide (17) resists attack at C-8 and only a very slow nucleophilic attack at C-10 by the enolate to give 18 is observed. Hydroxylic solvents do not allow any of these processes. (C) 2000 Published by Elsevier Science Ltd. All rights reserved.
• [8+2] Cycloaddition Reactions of 2H-Cyclohepta[b]furan-2-one with Acyclic 1,3-Dienes: A Facile Route to Novel Bicyclo [5.3.0] ring Systems
  作者：Vijay Nair、G Anilkumar、M.V Nandakumar、Bini Mathew、Nigam P Rath

  DOI：10.1016/s0040-4039(97)01472-x

  日期：1997.9

  Novel [8+2] cycloaddition reactions of 3-ethoxy carbonyl 2H-cyclohepta[b]furan-2-one with acyclic 1,3-dienes are described. The potential application of this process in the synthesis of modified colchicinoids incorporating bicyclo [5.3.0] ring systems has also been studied. © 1997 Elsevier Science Ltd.

  描述了3-乙氧基羰基2H-环庚[b]呋喃-2-酮与无环1,3-二烯的新型[8 + 2]环加成反应。还研究了该方法在结合双环[5.3.0]环系统的修饰类秋水仙碱合成中的潜在应用。©1997爱思唯尔科学有限公司。
• Cycloaddition reactions of 2-oxo-2H-cyclohepta[b]furan derivatives with dienes and dienophiles
  作者：Vijay Nair、M.V. Nandakumar、G. Anilkumar、Guenter K. Eigendorf

  DOI：10.1016/s0040-4020(99)00100-3

  日期：1999.3

  Cycloaddition reactions of 2-oxo-2H-cyclohepta[b]furan derivatives participating as 8π and 4π components respectively towards different dienes and dienophiles are described. The observed reactivity and periselectivity have been rationalized by AM1 calculations.

  描述了分别以8π和4π组分参与的2-oxo-2H-cyclohepta [b]呋喃衍生物对不同的二烯和双亲物的环加成反应。观察到的反应性和选择性是通过AM1计算合理化的。