(3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone | 171201-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone
• 英文别名: (3aR,5R,7aR)-5-hydroxy-7a-methyl-3,3a,4,5,6,7-hexahydro-1-benzofuran-2-one
• CAS: 171201-45-9
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: SDBYWKFFPVJMIV-ZXFLCMHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.85
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone 在 rhodium(III) chloride 吡啶 、 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 sodium hydride 、 臭氧 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.5h， 生成 (1'R,4'S,6'R,7'R,E)-1-tert-butoxycarbonyl-3-methyl-5-(1'-methyl-8'-oxo-9'-oxatricyclo[4.3.0.0^4,7]non-7'-yl)methylene-3-pyrrolin-2-one
  参考文献：
  名称：

  Total Synthesis of (+)-Ampullicin and (+)-Isoampullicin:  Two Fungal Metabolites with Growth Regulatory Activity Isolated from Ampulliferina Sp. 27

  摘要：

  The total synthesis of the growth regulators (+)-ampullicin 1 and (+)-isoampullicin 2 from (R)(-)-carvone 5 was accomplished by application of an 18-step sequence with 4.5% overall yield. The crucial step of the synthetic strategy lies on the internal displacement of tosylate 13 by means of the lactone enolate. In this way, access was opened to the tricyclic core present in these biologically active sesquiterpenic amides. A Horner-Emmons reaction between the carbaldehyde 16 and the phosphonate 22 led us to the stereoselective preparation of (+)-ampullicin 1. Standard transformation of I into the thermodynamically more stable geometric isomer (+)-isoampullicin 2 was trivial. The absolute configuration of both amides was established by X-ray analysis of a sample of synthetic (+)-isoampullicin 2.

  DOI：

  10.1021/jo010527+
• 作为产物：
  描述：

  (1R,5S)-香芹醇 在 甲醇 、 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 碳酸氢钠 、 臭氧 、 丙酸 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 85.0h， 生成 (3aR,5R,7aR)-5-hydroxy-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone
  参考文献：
  名称：

  Novel stereocontrolled synthesis of the tricyclic lactone (1R,3R,6R,9S)-6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonane

  摘要：

  The stereocontrolled synthesis of (1R,3R,6R,9S)-6,9-dimethyl-s-oxo-7-oxatricyclo[4.3.0.0(3,9)]nonane 1 from (R)-(-)-carvone has been accomplished by application of a 13-step sequence with 12% overall yield. The absolute stereochemistry of the unsaturated acid 8a has been established by X-ray analysis of the chiral amide 8c. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00641-1

文献信息

• Total synthesis of (−)-ampullicin and (+)-isoampullicin two growth regulators from Ampulliferina Sp. No. 27
  作者：Rosario Rico、Francisco Bermejo

  DOI：10.1016/0040-4039(95)01625-r

  日期：1995.10

  The growth regulators (-)-Ampullicin (1) and (+)-isoampullicin (2) have been synthesized utilizing carbaldehyde (25) as the chiral source and N-tertbutoxycarbonyl-3-methyl-2-(trimethylsiloxy)pyrrole (33) as the five-carbon homologative reagent. The synthesis of (1) and (2) is discussed in the context of retrosynthetic analysis. Carbaldehyde (25), has been prepared from both enantiomers of carvone, either (7) or (9), by application of a 15-step sequence with 4.7% and 5.4% overall yields respectively.