(1S,6R,7R,8S)-8-(3,4-Dimethoxy-phenyl)-3-methoxy-1,7-dimethyl-bicyclo[4.2.0]oct-3-ene-2,5-dione | 134360-70-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,6R,7R,8S)-8-(3,4-Dimethoxy-phenyl)-3-methoxy-1,7-dimethyl-bicyclo[4.2.0]oct-3-ene-2,5-dione
• 英文别名: (1S,6R,7R,8S)-8-(3,4-dimethoxyphenyl)-3-methoxy-1,7-dimethylbicyclo[4.2.0]oct-3-ene-2,5-dione
• CAS: 134360-70-6
• 化学式: C₁₉H₂₂O₅
• 分子量: 330.381
• InChiKey: RSQDQTPQQQFEMA-PBGQWVCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,6R,7R,8S)-8-(3,4-Dimethoxy-phenyl)-3-methoxy-1,7-dimethyl-bicyclo[4.2.0]oct-3-ene-2,5-dione 在 titanium(IV) isopropylate 、 (+)-4,5-双[羟基(二苯基)甲基]-2-甲基-2-苯基-1,3-二氧戊环 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (2S,3S)-2-(3,4-Dimethoxy-phenyl)-6-methoxy-3,4-dimethyl-2,3-dihydro-benzofuran-5-ol
  参考文献：
  名称：

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

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-1,2-二甲氧基-4-(1-丙烯基)苯 、 2-甲氧基-6-甲基对苯醌 在 titanium(IV) isopropylate 、 (+)-4,5-双[羟基(二苯基)甲基]-2-甲基-2-苯基-1,3-二氧戊环 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 生成 (1S,6R,7R,8S)-8-(3,4-Dimethoxy-phenyl)-3-methoxy-1,7-dimethyl-bicyclo[4.2.0]oct-3-ene-2,5-dione 、 (2S,3S)-2-(3,4-Dimethoxy-phenyl)-6-methoxy-3,4-dimethyl-2,3-dihydro-benzofuran-5-ol 、 (2R,3R)-2-(3,4-Dimethoxy-phenyl)-6-methoxy-3,4-dimethyl-2,3-dihydro-benzofuran-5-ol
  参考文献：
  名称：

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

  摘要：

  DOI：

文献信息

• 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：——
• 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.