(3aR,5S,7S,7aS)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone | 171201-42-6

• 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,5S,7S,7aS)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone
• 英文别名: (3aR,5S,7S,7aS)-7-bromo-7a-methyl-5-prop-1-en-2-yl-3,3a,4,5,6,7-hexahydro-1-benzofuran-2-one
• CAS: 171201-42-6
• 化学式: C₁₂H₁₇BrO₂
• 分子量: 273.17
• InChiKey: ZISXPZVXXWSNPM-WYFGTUCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3aR,5S,7S,7aS)-7-bromo-5-(2-propenyl)-7a-methyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone 在 咪唑 、 甲醇 、 二甲基硫 、 偶氮二异丁腈 、 三正丁基氢锡 、 sodium methylate 、 碳酸氢钠 、 臭氧 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.5h， 生成 (3aR,5R,7aR)-5-[tert-butyl(dimethyl)silyl]oxy-7a-methyl-3,3a,4,5,6,7-hexahydro-1-benzofuran-2-one
  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
• 作为产物：
  描述：

  (+)-(1R,5R)-5-Isopropenyl-2-methylcyclohex-2-enylacetic acid 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以86%的产率得到(3aR,5S,7S,7aS)-7-bromo-5-(2-propenyl)-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.
• Novel stereocontrolled synthesis of the tricyclic lactone (1R,3R,6R,9S)-6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.03,9]nonane
  作者：Rosario Rico、Julián Zapico、Francisco Bermejo、S.Bamidele Sanni、Santiago Garcı́a-Granda

  DOI：10.1016/s0957-4166(97)00641-1

  日期：1998.1

  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.