8,9-dihydroxy-1-acetoxy-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene | 156197-73-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 8,9-dihydroxy-1-acetoxy-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene
• 英文别名: (+/-)-4t-acetoxy-5,10t-dihydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthrone；5,10β-Dihydroxy-4β-acetoxy-9-oxo-1,4,4aα,9,9aα,10-hexahydro-anthracen；(+/-)-4t-acetoxy-5,10t-dihydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthrone；(+/-)-4t-Acetoxy-5,10t-dihydroxy-(4ar,9ac)-1,4,4a,9a-tetrahydro-anthron
• CAS: 156197-73-8；73794-50-0
• 化学式: C₁₆H₁₆O₅
• 分子量: 288.3
• InChiKey: SGHIINARMKQKQK-HTWGDNNSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  83.83
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  8,9-dihydroxy-1-acetoxy-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene 在 硫酸 作用下， 生成 1,10-diacetoxy-anthracene
  参考文献：
  名称：

  Inhoffen et al., Croatica Chemica Acta, 1957, vol. 29, p. 329,337

  摘要：

  DOI：
• 作为产物：
  描述：

  1-acetoxybuta-1,3-diene 在 三氟化硼乙醚 、 lithium tri-t-butoxyaluminum hydride 作用下， 反应 3.0h， 生成 8,9-dihydroxy-1-acetoxy-10-oxo-1(S),4,4a(R),9(S),9a(S),10-hexahydroanthracene
  参考文献：
  名称：

  11a-Chlorination of the Shemyakin tricyclic ketone

  摘要：

  DOI：

  10.1021/jo00140a043

文献信息

• 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
  作者：Koichi Mikami、Yukihiro Motoyama、Masahiro Terada

  DOI：10.1021/ja00086a014

  日期：1994.4

  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.
• Kolosov,M.N. et al., Journal of general chemistry of the USSR, 1964, vol. 34, p. 2558 - 2562
  作者：Kolosov,M.N. et al.

  DOI：——

  日期：——