((6R,8S)-8-Hydroxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-yl)-methanol | 176979-91-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: ((6R,8S)-8-Hydroxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-yl)-methanol
• 英文别名: [(6R,8S)-8-(hydroxymethyl)-5-(trityloxymethyl)-1,6,7,8-tetrahydrocyclopenta[g]indol-6-yl]methanol
• CAS: 176979-91-2
• 化学式: C₃₃H₃₁NO₃
• 分子量: 489.614
• InChiKey: IFLNZNYJTOMGFI-LOSJGSFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ((6R,8S)-8-Hydroxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-yl)-methanol 在 manganese(IV) oxide 、 18-冠醚-6 、 D(+)-10-樟脑磺酸 、 sodium hydride 、 三乙胺 、 sodium iodide 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 、 乙醚 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 (6R,8S)-1-Acetyl-6,8-dimethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole-5-carbaldehyde
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q
• 作为产物：
  描述：

  (6R,8S)-1-(2,2-Dimethyl-propionyl)-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indole-6,8-dicarbaldehyde 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到((6R,8S)-8-Hydroxymethyl-5-trityloxymethyl-1,6,7,8-tetrahydro-cyclopenta[g]indol-6-yl)-methanol
  参考文献：
  名称：

  Enantioselective Total Synthesis of cis-Trikentrin B

  摘要：

  Natural cis-trikentrin B was synthesized enantioselectively using, as key steps, an intramolecular Diels-Alder reaction of an allenic dienamide followed by aromatization to construct an indole ring and cleavage of bicyclo[2.2.1]heptene to launch a cis-dimethylcyclopentane ring. Diels-Alder adducts 9 and 10 were elaborated to provide allenic dienamide 25, and its intramolecular Diels-Alder reaction proceeded smoothly. Aromatization to an indole ring and stereoselective cleavage of the bicyclo[2.2.1]heptene ring were performed successfully. Introduction of an (E)-butenyl group via addition of propylmagnesium bromide and subsequent anti elimination of water gave natural cis-trikentrin B.

  DOI：

  10.1021/jo951767q