(1R,9S,10R,15S)-13-methoxytetracyclo[7.6.0.02,7.010,15]pentadeca-2,4,6,12-tetraene-11,14-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1R,9S,10R,15S)-13-methoxytetracyclo[7.6.0.02,7.010,15]pentadeca-2,4,6,12-tetraene-11,14-dione
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: QKAJQOCEXLULNU-PUPMMZHASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲氧苯醌 、 茚 在 titanium(IV) isopropylate 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 以85%的产率得到(1R,9S,10R,15S)-13-methoxytetracyclo[7.6.0.02,7.010,15]pentadeca-2,4,6,12-tetraene-11,14-dione
  参考文献：
  名称：

  烯烃和醌的立体选择性 3 + 2 和立体选择性 2 + 2 环加成反应

  摘要：

  pH 7.0.14 的 mM NaCl 和 25 mM tris-乙酸盐 在 24 ℃下孵育 0.5 小时后，加入 4 mM 二硫苏糖醇以启动链裂解。使反应持续 6 小时（24°C）。双链切割产物在 0.4% 垂直琼脂糖凝胶上分离，该凝胶可解析大小高达 25 kbp 的 DNA 片段（图 3）。因此，DNA 在R 和

  DOI：

  10.1021/ja00231a084

文献信息

• Stereoselective 3 + 2 and stereospecific 2 + 2 cycloaddition reactions of alkenes and quinones
  作者：Thomas A. Engler、Keith D. Combrink、James E. Ray

  DOI：10.1021/ja00231a084

  日期：1988.11

  mM NaCl and 25 mM tris-acetate at pH 7.0.14 After 0.5 h incubation at 24 OC, 4 mM dithiothreitol was added to initiate strand cleavage. The reaction was allowed to continue for 6 h (24 "C). The double strand cleavage products were separated on a 0.4% vertical agarose gel which resolves DNA segments up to 25 kbp in size (Figure 3). Therefore, DNA uniquely labeled at the R and

  pH 7.0.14 的 mM NaCl 和 25 mM tris-乙酸盐 在 24 ℃下孵育 0.5 小时后，加入 4 mM 二硫苏糖醇以启动链裂解。使反应持续 6 小时（24°C）。双链切割产物在 0.4% 垂直琼脂糖凝胶上分离，该凝胶可解析大小高达 25 kbp 的 DNA 片段（图 3）。因此，DNA 在R 和
• Asymmetric Reactions of 2-Methoxy-1,4-benzoquinones with Styrenyl Systems:  Enantioselective Syntheses of 8-Aryl-3-methoxybicyclo[4.2.0]oct-3-en-2,5-diones, 7-Aryl-3-hydroxybicyclo[3.2.1]oct-3-en-2,8-diones, 2-Aryl-6-methoxy-2,3-dihydrobenzofuran-5-ols, and Pterocarpans
  作者：Thomas A. Engler、Michael A. Letavic、Rajesh Iyengar、Kenneth O. LaTessa、Jayachandra P. Reddy

  DOI：10.1021/jo982164s

  日期：1999.4.1

  Reactions of 2-methoxy-1,4-benzoquinones 2 and 3 with (E)-propenylbenzenes 1 promoted at -78 degrees C by Ti(IV)-TADDOLates prepared from diol-(+)- 4 afford (1R,6R,7R,8R)-8-aryl-3-methoxy-7methylbicyclo[4.2.0]oct-3-en-2,5-diones 5/8 or (1R,5R,6R,7R)-7-aryl-3-hydroxy-6-methylbicyclo-3-en-2,8-diones 7/10 in good yield and high ee. (2S,3S)-2-Aryl-6-methoxy-3-methyl-2,3-dihydrobenzofuran-5-ols 6/9 are also found, but in slightly lower ee. Cyclobutanes 5/8 cleanly and efficiently rearrange to the dihydrobenzofurans 6/9 without loss of enantiomeric purity upon treatment with the Ti-TADDOLates at higher temperatures. Reactions of (Z)-propenylbenzene 17 and of indene with 2 and 3 give products in moderate enantiomeric purity. Products obtained from reactions of 1-anisylcycloalkenes with 2 differ significantly in yield and enantiomeric purity. In the latter reactions, the ee's of the cyclobutane products are consistently much higher than those of the dihydrobenzofuran products. More significantly, products of different absolute configuration result from different cycloalkenes. With 1-anisylcyclopentene or 1-anisylcyclohexene, all of the products are of similar configuration and are obtained in comparable yields and ee's. However, 1-anisylcycloheptene affords products that are diastereomeric with those of the 1-anisylcyclopentene, and in lower ee's. A mechanistic model is proposed. Application of these reactions to the enantioselective synthesis of the pterocarpan class of isoflavonoid natural products is also reported.
• ENGLER, THOMAS A.;COMBRINK, KEITH D.;RAY, JAMES E., J. AMER. CHEM. SOC., 110,(1988) N 23, C. 7931-7933
  作者：ENGLER, THOMAS A.、COMBRINK, KEITH D.、RAY, JAMES E.

  DOI：——

  日期：——
• Engler, Thomas A.; Letavic, Michael A.; Reddy, Jayachandra P., Journal of the American Chemical Society, 1991, vol. 113, # 13, p. 5068 - 5070
  作者：Engler, Thomas A.、Letavic, Michael A.、Reddy, Jayachandra P.

  DOI：——

  日期：——