1-acetoxy-8-hydroxy-1,4,4a,9a-tetrahydroanthraquinone | 73794-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1-acetoxy-8-hydroxy-1,4,4a,9a-tetrahydroanthraquinone
• 英文别名: 1-acetoxy-8-hydroxy-9,10-dioxo-1,4,4a,9,9a,10-hexahydroanthracene；(+/-)-1t-acetoxy-8-hydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthraquinone；(+/-)-1t-Acetoxy-8-hydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthrachinon；(+)-1-Acetoxy-8-hydroxy-1,4,4a,9a-tetrahydro-anthraquinone；[(1S,4aR,9aR)-8-hydroxy-9,10-dioxo-1,4,4a,9a-tetrahydroanthracen-1-yl] acetate
• CAS: 73794-49-7
• 化学式: C₁₆H₁₄O₅
• 分子量: 286.284
• InChiKey: BPPAROUEECPSAP-SCDSUCTJSA-N

物化性质

• 沸点：
  495.4±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-acetoxy-8-hydroxy-1,4,4a,9a-tetrahydroanthraquinone 生成 4β-Acetoxy-5,10β-isopropylidendioxy-9-oxo-1,4,4aα,9,9aα,10-hexahydro-anthracen
  参考文献：
  名称：

  KELLY T. R.; WHITING A.; CHANDRAKUMAR N. S., J. AMER. CHEM. SOC., 108,(1986) N 12, 3510-3512

  摘要：

  DOI：
• 作为产物：
  描述：

  1-乙酰氧基-1,3-丁二烯 、 5-羟基对萘醌 在 二异丙氧基二氯化钛 、 S-1,1'-联-2-萘酚 作用下， 以 二氯甲烷 为溶剂， 反应 19.0h， 生成 1-acetoxy-8-hydroxy-1,4,4a,9a-tetrahydroanthraquinone
  参考文献：
  名称：

  Asymmetric Catalysis of Diels-Alder Cycloadditions by an MS-Free Binaphthol-Titanium Complex: Dramatic Effect of MS, Linear vs Positive Nonlinear Relationship, and Synthetic Applications

  摘要：

  Asymmetric Diels-Alder (D.-A.) reaction of 5-hydroxynaphthoquinone (juglone) with butadienyl acetate catalyzed by the binaphthol-derived chiral titanium (BINOL-Ti) complex 1 proceeds in only 9% ee in the presence of molecular sieves (MS). Remarkably, however, this reaction proceeds in 76-96% ee with BINOL-Ti complex 1 freed from MS to provide the endo-adducts useful for the synthesis of anthracyclines and tetracyclines. The solid MS-free BINOL-Ti complex 1 is stable for months at -20 degrees C, Enhancements in endo selectivity and asymmetric induction are observed with the MS-free BINOL-Ti 1 also in the catalyzed D.-A. cycloaddition of methacrolein and glyoxylate with 1,3-dienol ethers and esters. The glyoxylate adducts can be converted to the mevinolin (compactin) intermediates. Surprisingly, the MS-free complex 1 exhibits not only a linear relationship between the ee's of BINOL-Ti 1 and the D.-A. products but also a positive nonlinear effect (asymmetric amplification), depending simply on the mixing manner of (R)-1 with (S)-1 or (+/-)-1.

  DOI：

  10.1021/ja00086a014

文献信息

• The ‘Mikami’-Catalyst in Enantioselective Diels–Alder Reactions of Juglone-Based Dienophiles with Different 1-Oxygenated Dienes: An Investigation on the Substitution Pattern Dependent Regioselectivity
  作者：Jörg Pietruszka、Dietrich Böse、Wolfgang Frey

  DOI：10.1055/s-0034-1378230

  日期：——

  investigating the substitution pattern depending regioselectivity of enantioselective BINOL-Ti-catalyzed­ Diels–Alder reactions of juglone-based dienophiles with 1-oxygenated dienes is reported. The different influences of residues both on the diene as well as on the dienophiles are investigated giving a detailed picture of their role on the regioselectivity. A mechanistic study investigating the substitution

  摘要 一项机理研究研究了取代模式，该模式取决于对映体选择性的BINOL-Ti催化的基于Juglone的双亲亲烯与1-氧化二烯的Diels-Alder反应的区域选择性。研究了残基对二烯以及对亲二烯物的不同影响，给出了其对区域选择性作用的详细描述。 一项机理研究研究了取代模式，该模式取决于对映体选择性的BINOL-Ti催化的基于Juglone的双亲亲烯与1-氧化二烯的Diels-Alder反应的区域选择性。研究了残基对二烯以及对亲二烯物的不同影响，给出了其对区域选择性作用的详细描述。
• Inhoffen et al., Croatica Chemica Acta, 1957, vol. 29, p. 329,337
  作者：Inhoffen et al.

  DOI：——

  日期：——
• Rationally designed, chiral Lewis acid for the asymmetric induction of some Diels-Alder reactions
  作者：T. Ross. Kelly、Andrew. Whiting、Nizal S. Chandrakumar

  DOI：10.1021/ja00272a058

  日期：1986.6
• 11a-Chlorination of the Shemyakin tricyclic ketone
  作者：Britt Marie G. Gaveby、John C. Huffman、Philip Magnus

  DOI：10.1021/jo00140a043

  日期：1982.9