(6R,8E)-6,8-dimethyl-9-iodo-8-nonenal | 214261-02-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6R,8E)-6,8-dimethyl-9-iodo-8-nonenal
• 英文别名: (E,6R)-9-iodo-6,8-dimethylnon-8-enal
• CAS: 214261-02-6
• 化学式: C₁₁H₁₉IO
• 分子量: 294.176
• InChiKey: KXORLLWTMLSWMP-OYVNLZQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (6R,8E)-6,8-dimethyl-9-iodo-8-nonenal 在 4 Angstroem MS 、 calcium carbonate 作用下， 以 甲苯 为溶剂， 反应 26.0h， 生成 (2R,3R,3aR,4R,4aR,5S,8R,8aS,5'S,7E)-2-(5',7'-dimethyl-8'-iodo-7'-octen-1'-yl)-5,10,10-trimethyl-5,8-methanooctahydro-2H-isoxazolo[3,2-b]benzoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u
• 作为产物：
  描述：

  (3S,5E)-6-iodo-3,5-dimethyl-5-hexenal 在 盐酸 、 氢氧化钾 、 正丁基锂 、 盐酸羟胺 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (6R,8E)-6,8-dimethyl-9-iodo-8-nonenal
  参考文献：
  名称：

  Oxazoline N-Oxide-Mediated [2 + 3] Cycloadditions: Application to a Total Synthesis of the Hypocholesterolemic Agent 1233A

  摘要：

  Oxetanone 1233A1 has been synthesized in 22 steps and 3.43% overall yield from 3-methylglutaric anhydride. Asymmetric carbon at C-7 was introduced by a diastereoselective esterification of 3-methylglutaric anhydride, whereas the two asymmetric carbons at C-2' and C-3' were controlled by an asymmetric [2 +/- 3] cycloaddition using camphor-derived oxazoline N-oxide as dipole.

  DOI：

  10.1021/jo980813u