5H-benzocycloheptene-6,8-dicarboxylic acid-6,7,8,9-tetrahydro-5,9-dioxo-6,8-dimethyl ester | 6496-77-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5H-benzocycloheptene-6,8-dicarboxylic acid-6,7,8,9-tetrahydro-5,9-dioxo-6,8-dimethyl ester
• 英文别名: 4,6-dicarbomethoxy-1,2-benzo-1-cycloheptene-3,7-dione；1,5-Dioxo-1,2,4,5-tetrahydro-3H-benzo<6,7>cycloheptan-2,4-dicarbonsaeure-dimethylester；4,6-Dimethoxycarbonyl-1,2-benzo-cyclohept-1-en-3,7-dion；dimethyl 5,9-dioxo-7,8-dihydro-6H-benzo[7]annulene-6,8-dicarboxylate
• CAS: 6496-77-1
• 化学式: C₁₅H₁₄O₆
• 分子量: 290.273
• InChiKey: JRUVWPQNEXOZTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5H-benzocycloheptene-6,8-dicarboxylic acid-6,7,8,9-tetrahydro-5,9-dioxo-6,8-dimethyl ester 在 盐酸 、 L-Selectride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙二醇二甲醚 、 水 为溶剂， 反应 27.5h， 生成 meso-6,7,8,9-tetrahydro-5H-benzocycloheptene-5,9-diol
  参考文献：
  名称：

  Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

  摘要：

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.103
• 作为产物：
  描述：

  戊二酸二甲酯 、 邻苯二甲酸二甲酯 在 sodium hydride 作用下， 以 1,4-二氧六环 、 甲醇 、 mineral oil 为溶剂， 反应 22.0h， 以40%的产率得到5H-benzocycloheptene-6,8-dicarboxylic acid-6,7,8,9-tetrahydro-5,9-dioxo-6,8-dimethyl ester
  参考文献：
  名称：

  Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands

  摘要：

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.12.103

文献信息

• An Expeditious Synthesis of Dimethyl 1-Benzyl-<i>cis</i>-Piperidine-3,5-Dicarboxylate
  作者：Bruno Danieli、Giordano Lesma、Daniele Passarella、Alessandra Silvani

  DOI：10.1080/00397919708004806

  日期：1997.1.1

  A mixture of dimethyl 1-benzyl-cis- and trans-piperidine-3,5-dicarboxylate is prepared in high yields from readily available starting materials, by a reliable procedure. The straightforward conversion of the mixture into the diastereomerically pure cis-isomer, a useful sigma-symmetry intermediate for alkaloid synthesis, is also described.
• Hahn,W.E.; Kryczka,B., Polish Journal of Chemistry, 1979, vol. 53, p. 1751 - 1764
  作者：Hahn,W.E.、Kryczka,B.

  DOI：——

  日期：——
• HAHN W. E.; KRYCZKA B., POL. J. CHEM., 1979, 53, NO 9, 1751-1764
  作者：HAHN W. E.、 KRYCZKA B.

  DOI：——

  日期：——
• Aerobic oxidative desymmetrization of meso-diols with bifunctional amidoiridium catalysts bearing chiral N-sulfonyldiamine ligands
  作者：Junki Moritani、Yasuharu Hasegawa、Yoshihito Kayaki、Takao Ikariya

  DOI：10.1016/j.tetlet.2013.12.103

  日期：2014.2

  Asymmetric aerobic oxidation of a range of meso- and prochiral diols with chiral bifunctional Ir catalysts is described. A high level of chiral discrimination ability of Cp*Ir complexes derived from (S,S)-1,2-diphenylethylenediamine was successfully demonstrated by desymmetrization of secondary benzylic diols such as cis-indan-1,3-diol and cis-1,4-diphenylbutane-1,4-diol, providing the corresponding (R)-hydroxyl ketones with excellent chemo- and enantioselectivities. Enantiotopic group discrimination in oxidation of symmetrical primary 1,4- and 1,5-diols gave rise to chiral lactones with moderate ees under similar aerobic conditions. (C) 2014 Elsevier Ltd. All rights reserved.