4-(S)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-pentanal | 80850-81-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-(S)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-pentanal
• 英文别名: (4S)-4-[(1S,4R)-5-methoxy-4,7-dimethyl-1,2,3,4-tetrahydronaphthalen-1-yl]pentanal
• CAS: 80850-81-3
• 化学式: C₁₈H₂₆O₂
• 分子量: 274.403
• InChiKey: DENBOIYXMDIKJM-ZNMIVQPWSA-N

物化性质

• 沸点：
  386.7±42.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  4-(S)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-pentanal 在 platinum(IV) oxide 、 palladium on activated charcoal 氢气 、 三溴化硼 、 potassium carbonate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -70.0~100.0 ℃ 、6.89 MPa 条件下， 反应 66.17h， 生成 (7S,10R)-trans-calamenene
  参考文献：
  名称：

  Bunko, Julian D.; Ghisalberti, Emilio L.; Jefferies, Phillip R., Australian Journal of Chemistry, 1981, vol. 34, # 10, p. 2237 - 2242

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(R)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-propan-1-ol 在 草酰氯 、 palladium on activated charcoal 、 氢气 、 二异丁基氢化铝 、 二甲基亚砜 作用下， 以 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 192.0h， 生成 4-(S)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-pentanal
  参考文献：
  名称：

  Total synthesis and structural confirmation of the antibacterial diterpene leubethanol

  摘要：

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.082

文献信息

• Bunko, Julian D.; Ghisalberti, Emilio L.; Jefferies, Phillip R., Australian Journal of Chemistry, 1981, vol. 34, # 10, p. 2237 - 2242
  作者：Bunko, Julian D.、Ghisalberti, Emilio L.、Jefferies, Phillip R.

  DOI：——

  日期：——
• Total synthesis and structural confirmation of the antibacterial diterpene leubethanol
  作者：Jessica M.H. Lu、Michael V. Perkins、Hans J. Griesser

  DOI：10.1016/j.tet.2013.05.082

  日期：2013.8

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.