1-acetoxy-8,9-(isopropylidenedioxy)-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene | 102490-06-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-acetoxy-8,9-(isopropylidenedioxy)-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene
• CAS: 102490-06-2
• 化学式: C₁₉H₂₀O₅
• 分子量: 328.365
• InChiKey: KONDIQVKBWXNLR-CWYPUQQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  24.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-acetoxy-8,9-(isopropylidenedioxy)-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene 生成 (7aR,11S,11aR,11bS)-11-Hydroxy-2,2-dimethyl-8,11,11a,11b-tetrahydro-7aH-1,3-dioxa-benzo[de]anthracen-7-one
  参考文献：
  名称：

  Rationally designed, chiral Lewis acid for the asymmetric induction of some Diels-Alder reactions

  摘要：

  DOI：

  10.1021/ja00272a058
• 作为产物：
  描述：

  1-乙酰氧基-1,3-丁二烯 在 sodium tetrahydroborate 、 二异丙氧基二氯化钛 、 S-1,1'-联-2-萘酚 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 47.25h， 生成 1-acetoxy-8,9-(isopropylidenedioxy)-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene
  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