Dimethyl (9S,10S)-2,6-di-tert-butyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate | 272111-36-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: Dimethyl (9S,10S)-2,6-di-tert-butyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate
• CAS: 272111-36-1
• 化学式: C₂₈H₃₂O₄
• 分子量: 432.56
• InChiKey: PYDAIVWXGYJLBB-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.52
• 重原子数：
  32.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Dimethyl (9S,10S)-2,6-di-tert-butyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate 在 氰化钠 、 氨 作用下， 以 甲醇 为溶剂， 反应 120.0h， 以77%的产率得到(9S,10S)-2,6-Di-tert-butyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylic acid diamide
  参考文献：
  名称：

  A Highly Enantiopure Biconcave Porphyrin with Effective D4-Structure

  摘要：

  A first representative of an effectively D-4-symmetric biconcave porphyrin (1) was prepared from a tetramerizing condensation of a C-2-symmetric pyrrole (2). The chiral pyrrole 2 was synthesized in a six-step reaction sequence starting from the C-2h-symmetric 2,6-di-tert-butylanthracene. The relevant stereochemistry was introduced in a highly diastereo-discriminating Diels-Alder reaction with fumaric acid di(-)menthyl ester, catalyzed by aluminum chloride, X-ray analyses of two of the dimenthyl esters prepared unambiguously secured their tentatively assigned absolute configuration and that of the pyrrole 2 (as the S,S isomer). The enantiomeric purity of the pyrrole 2 was determined as 99% ee, using the Co-II complex of the porphyrin 1 as a chiral shift reagent. The pyrrole 2 lent itself to a stereochemically nearly uniform preparation of the chiral, biconcave porphyrin 1, Applying Horeau's principle, 1 was calculated to be present in an enantiomeric excess of about 10(9):1. The validity of the statistical considerations relevant for this estimate were verified by examination of the results from preparative tetramerization experiments in which the enantiomeric purity of the pyrrole 2 was deliberately lowered.

  DOI：

  10.1002/(sici)1521-3765(20000403)6:7<1214::aid-chem1214>3.3.co;2-a
• 作为产物：
  描述：

  Di[(1R)-menthyl] (9S,10S,11S,12S)-2,6-di-tert-butyl-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate 在 甲烷磺酸 、 二苯基二硒醚 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 108.0h， 生成 Dimethyl (9S,10S)-2,6-di-tert-butyl-9,10-dihydro-9,10-ethenoanthracene-11,12-dicarboxylate
  参考文献：
  名称：

  A Highly Enantiopure Biconcave Porphyrin with Effective D4-Structure

  摘要：

  A first representative of an effectively D-4-symmetric biconcave porphyrin (1) was prepared from a tetramerizing condensation of a C-2-symmetric pyrrole (2). The chiral pyrrole 2 was synthesized in a six-step reaction sequence starting from the C-2h-symmetric 2,6-di-tert-butylanthracene. The relevant stereochemistry was introduced in a highly diastereo-discriminating Diels-Alder reaction with fumaric acid di(-)menthyl ester, catalyzed by aluminum chloride, X-ray analyses of two of the dimenthyl esters prepared unambiguously secured their tentatively assigned absolute configuration and that of the pyrrole 2 (as the S,S isomer). The enantiomeric purity of the pyrrole 2 was determined as 99% ee, using the Co-II complex of the porphyrin 1 as a chiral shift reagent. The pyrrole 2 lent itself to a stereochemically nearly uniform preparation of the chiral, biconcave porphyrin 1, Applying Horeau's principle, 1 was calculated to be present in an enantiomeric excess of about 10(9):1. The validity of the statistical considerations relevant for this estimate were verified by examination of the results from preparative tetramerization experiments in which the enantiomeric purity of the pyrrole 2 was deliberately lowered.

  DOI：

  10.1002/(sici)1521-3765(20000403)6:7<1214::aid-chem1214>3.3.co;2-a