(1R,2R,4aS,8aS)-2-(epoxymethylene)-5,5,8a-trimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1-naphthaleneacetaldehyde | 178458-50-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,4aS,8aS)-2-(epoxymethylene)-5,5,8a-trimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1-naphthaleneacetaldehyde
• CAS: 178458-50-9
• 化学式: C₁₆H₂₆O₂
• 分子量: 250.381
• InChiKey: OYXMVJHDINQLQS-XRGAULLZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  29.6
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1R,2R,4aS,8aS)-2-(epoxymethylene)-5,5,8a-trimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1-naphthaleneacetaldehyde 在 正丁基锂 、 氧气 、 rose bengal 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 8.5h， 生成 (S)-5-Hydroxy-4-((2S,3aR,5aS,9aS,9bR)-3a-hydroxymethyl-6,6,9a-trimethyl-dodecahydro-naphtho[2,1-b]furan-2-yl)-dihydro-furan-2-one
  参考文献：
  名称：

  Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide

  摘要：

  The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported, Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with O-1(2) in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b, An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).

  DOI：

  10.1021/jo971631n
• 作为产物：
  描述：

  香紫苏内酯 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 dipyridine chromium trioxide 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (1R,2R,4aS,8aS)-2-(epoxymethylene)-5,5,8a-trimethyl-1,2,3,4,4a,5,6,7,8,8a-decahydro-1-naphthaleneacetaldehyde
  参考文献：
  名称：

  Synthesis of Acuminolide and 17-O-Acetylacuminolide from (+)-Sclareolide

  摘要：

  The synthesis of natural acuminolide and 17-O-acetylacuminolide is reported, Commerically available (+)-sclareolide was converted to epoxy alcohol 3, which upon acid-catalyzed cyclization afforded tricycle 14. Reaction of 14 with O-1(2) in the presence of a hindered base gave an inseparable mixture of acuminolide 1a and 16-epiacuminolide 1b in a 70:30 ratio. Chromatographic separation of the diacetates of 1a and 1b afforded pure 18a and 18b, An analogous reaction sequence was used in the synthesis of 17-O-acetylacuminolide (2a) and 16-epi-17-O-acetylacuminolide (2b).

  DOI：

  10.1021/jo971631n

文献信息

• Synthesis of nor-norambracetal
  作者：Frédéric Chauvet、Ivan Coste-Manière、Paul Martres、Patricia Perfetti、Bernard Waegell、Jean-Pierre Zahra

  DOI：10.1016/0040-4039(96)00697-1

  日期：1996.5

  We describe the synthesis of nor-norambracetal 13 from sclareol 1, using γ-homobicyclo-farnesylic alcohol 3 as a key intermediate.

  我们描述了使用γ-同双环法呢醇3作为关键中间体，从香紫苏1中合成正降醛缩醛13。
• Zahra, Jean-Pierre; Chauvet, Frederic; Coste-Maniere, Ivan, Bulletin de la Societe Chimique de France, 1997, vol. 134, # 10,11, p. 1001 - 1024
  作者：Zahra, Jean-Pierre、Chauvet, Frederic、Coste-Maniere, Ivan、Martres, Paul、Perfetti, Patricia、Waegell, Bernard

  DOI：——

  日期：——