methyl 2-(ethylenedioxy)-1α,4aβ,8aβ-trimethyl-8-oxo-1,2,3,4,4a,6,7,8,8a,9-decahydrophenanthrene-7α-carboxylate | 131250-73-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-(ethylenedioxy)-1α,4aβ,8aβ-trimethyl-8-oxo-1,2,3,4,4a,6,7,8,8a,9-decahydrophenanthrene-7α-carboxylate
• 英文别名: methyl (2'R,4'bR,8'R,10'aS)-4'b,8',10'a-trimethyl-1'-oxospiro[1,3-dioxolane-2,7'-2,3,5,6,8,10-hexahydrophenanthrene]-2'-carboxylate
• CAS: 131250-73-2
• 化学式: C₂₁H₂₈O₅
• 分子量: 360.45
• InChiKey: IVYDDEFILDEWPO-FQZPYLGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 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：

  methyl 2-(ethylenedioxy)-1α,4aβ,8aβ-trimethyl-8-oxo-1,2,3,4,4a,6,7,8,8a,9-decahydrophenanthrene-7α-carboxylate 在 吡啶 、 sodium tetrahydroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  Total synthesis of (.+-.)-amarolide, a quassinoid bitter principle

  摘要：

  The first total synthesis of amarolide (1), a bitter tasting quassinoid having a picrasane skeleton with 10 chiral centers, is described in racemic form. The synthesis of (+/-)-1 was accomplished stereoselectively in 35 steps and 0.5% overall yield from a known tricyclic compound 7. An orthoester Claisen rearrangement and a lead tetraacetate oxidation were utilized as key reactions to prepare hydroxy ketone 14 with a complete picrasane skeleton. This hydroxy ketone was transformed into 1 in 18 steps that included 1,3-carbonyl transposition, introduction of hydroxyl groups at C-2 and C-11 positions, and oxidation of an ether to afford a delta-lactone.

  DOI：

  10.1021/jo00003a039
• 作为产物：
  描述：

  (4'bR,8'R,10'aS)-4'b,8',10'a-trimethylspiro[1,3-dioxolane-2,7'-2,3,5,6,8,10-hexahydrophenanthrene]-1'-one 、 碳酸二甲酯 在 potassium hydride 、 sodium hydride 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 以100%的产率得到methyl 2-(ethylenedioxy)-1α,4aβ,8aβ-trimethyl-8-oxo-1,2,3,4,4a,6,7,8,8a,9-decahydrophenanthrene-7α-carboxylate
  参考文献：
  名称：

  Total synthesis of (.+-.)-amarolide, a quassinoid bitter principle

  摘要：

  The first total synthesis of amarolide (1), a bitter tasting quassinoid having a picrasane skeleton with 10 chiral centers, is described in racemic form. The synthesis of (+/-)-1 was accomplished stereoselectively in 35 steps and 0.5% overall yield from a known tricyclic compound 7. An orthoester Claisen rearrangement and a lead tetraacetate oxidation were utilized as key reactions to prepare hydroxy ketone 14 with a complete picrasane skeleton. This hydroxy ketone was transformed into 1 in 18 steps that included 1,3-carbonyl transposition, introduction of hydroxyl groups at C-2 and C-11 positions, and oxidation of an ether to afford a delta-lactone.

  DOI：

  10.1021/jo00003a039

文献信息

• HIROTA, HIROSHI;YOKOYAMA, AKIHISA;MIYAJI, KATSUAKI;NAKAMURA, TOSHIO;IGARA+, J. ORG. CHEM., 56,(1991) N, C. 1119-1127
  作者：HIROTA, HIROSHI、YOKOYAMA, AKIHISA、MIYAJI, KATSUAKI、NAKAMURA, TOSHIO、IGARA+

  DOI：——

  日期：——