2α,3α-epoxy-1α,4α-dihydro-1,4-methanoanthracene-9,10-dione | 207133-46-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 并四苯
• 英文名称: 2α,3α-epoxy-1α,4α-dihydro-1,4-methanoanthracene-9,10-dione
• 英文别名: (1R,12S,13S,15R)-14-oxapentacyclo[10.3.1.02,11.04,9.013,15]hexadeca-2(11),4,6,8-tetraene-3,10-dione
• CAS: 207133-46-8
• 化学式: C₁₅H₁₀O₃
• 分子量: 238.243
• InChiKey: OKSZNUAWNIGZHF-NWQDQBDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2α,3α-epoxy-1α,4α-dihydro-1,4-methanoanthracene-9,10-dione 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (1RS,2SR,11SR,12SR,13SR,14SR)-11-(acetoxy)-3,10-dioxopentacyclo[10.2.0^2,11.0^2,14.0^4,9]pentadeca-4(9),5,7-trien-13-yl acetate
  参考文献：
  名称：

  Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes

  摘要：

  Acid promoted ring opening of 1 alpha,4 alpha,4a alpha,9a alpha-tetrahydro-2 beta-3 beta-epoxy-1,4-methanoanthracene-9,10-dione and the corresponding 2-methyl derivative (i.e., 3a and 3b, respectively) afforded 4a and 46 in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 46 along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of 1 alpha,4 alpha-dihydro-4a alpha,9a alpha-epoxy-1,4-methanoanthracene-9,10-dione (12) resulted in extensive skeletal rearrangement of the substrate, thereby affording 14 in low yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00162-8
• 作为产物：
  描述：

  1,4-二氢-1,4-甲桥蒽-9,10-二酮 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以64%的产率得到2α,3α-epoxy-1α,4α-dihydro-1,4-methanoanthracene-9,10-dione
  参考文献：
  名称：

  Synthesis and acid- and base-promoted ring opening of polycarbocyclic oxiranes

  摘要：

  Acid promoted ring opening of 1 alpha,4 alpha,4a alpha,9a alpha-tetrahydro-2 beta-3 beta-epoxy-1,4-methanoanthracene-9,10-dione and the corresponding 2-methyl derivative (i.e., 3a and 3b, respectively) afforded 4a and 46 in 26% and 49% yield, respectively. Similar results were obtained when a solution of either 3a or 3b in aqueous acetone was reacted with Na2CO3 at ambient temperature for 2 days. However, reaction of 3b with aqueous methanolic NaOH (ambient temperature, 7 days) produced a small quantity of 46 along with a novel pentacyclic diketone, 6b (44% yield). Finally, acid promoted ring opening of 1 alpha,4 alpha-dihydro-4a alpha,9a alpha-epoxy-1,4-methanoanthracene-9,10-dione (12) resulted in extensive skeletal rearrangement of the substrate, thereby affording 14 in low yield. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00162-8

文献信息

• Experimental and theoretical investigations into the stereoselectivities of peracid promoted epoxidations of substituted norbornenes and norbornadienes
  作者：Alan P Marchand、Bishwajit Ganguly、Rajesh Shukla、Kasireddy Krishnudu、V Satish Kumar、William H Watson、Satish G Bodige

  DOI：10.1016/s0040-4020(99)00464-0

  日期：1999.7

  MCPBA promoted diastereoselective epoxidations of functionalized norbornenes and norbornadienes have been performed, The experimental results thereby obtained have been evaluated by using semiempirical (AMI) quantum chemical modeling. The AMI computational results are consistent with experiment and correctly predict the major product of all MCPBA promoted epoxidations studied herein. Product characterization was assisted via the results of X-ray crystallographic structural analysis in the case of 10a and by comparison of calculated vs. experimental C-13 NMR chemical shifts of the cyclopropyl carbon atoms in 12a and 12b. (C) 1999 Elsevier Science Ltd. All rights reserved.