(3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone | 204526-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone
• 英文别名: [(3R,3aR,5R,7aR)-3,7a-dimethyl-2-oxo-3,3a,4,5,6,7-hexahydro-1-benzofuran-5-yl] 4-methylbenzenesulfonate
• CAS: 204526-17-0
• 化学式: C₁₇H₂₂O₅S
• 分子量: 338.425
• InChiKey: RKWNZFROOAVUCH-GKLJAUDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-3a,4,5,6,7,7a-hexahydro-2(3H)-benzofuranone 在 六甲基磷酰三胺 、 lithium diisopropyl amide 作用下， 生成 6,9-dimethyl-8-oxo-7-oxatricyclo[4.3.0.0^3.9]nonane
  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 吡啶 、 咪唑 、 甲醇 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 二甲基硫 、 偶氮二异丁腈 、 四丁基氟化铵 、 三正丁基氢锡 、 sodium methylate 、 碳酸氢钠 、 臭氧 、 间氯过氧苯甲酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 72.5h， 生成 (3R,3aR,5R,7aR)-5-[(4-methylbenzene)-1-sulfonyloxy]-3,7a-dimethyl-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

• 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.