(5S,8R)-3,8-dimethyl-5-[6-methylhept-5-en-2-(R)-yl]-1-methoxy-5,6,7,8-tetrahydronaphthalene | 1384113-67-0

• 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: (5S,8R)-3,8-dimethyl-5-[6-methylhept-5-en-2-(R)-yl]-1-methoxy-5,6,7,8-tetrahydronaphthalene
• 英文别名: leubethanol methyl ether；(1S,4R)-5-methoxy-4,7-dimethyl-1-[(2S)-6-methylhept-5-en-2-yl]-1,2,3,4-tetrahydronaphthalene
• CAS: 1384113-67-0
• 化学式: C₂₁H₃₂O
• 分子量: 300.484
• InChiKey: YNUXCQWYBPEGLY-KSZLIROESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (5S,8R)-3,8-dimethyl-5-[6-methylhept-5-en-2-(R)-yl]-1-methoxy-5,6,7,8-tetrahydronaphthalene 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以80%的产率得到(-)-leubethanol
  参考文献：
  名称：

  通过环戊酮的催化 CC 活化来不对称全合成二萜和倍半萜。

  摘要：

  为了展示催化 CC 活化对张力较小的底物的合成效用，这里描述了天然产物 (-)-microthecaline A、(-)-leubehanol、(+)-pseudopteroxodium、(+)- 的集体和简明合成。 seco-pseudopteroxilla、pseudopterosin AF 和 GJ 苷元以及 (+)-heritinin。这些合成的关键步骤涉及 Rh 催化的 3-芳基环戊酮的 CC/CH 活化级联，这提供了一种快速且对映选择性的途径来获取这些天然产物中存在的多取代四氢萘核心。其他重要特征包括 1) 在 (-)-微壳碱 A 合成中对四氢萘酮底物进行直接 CH 胺化，2) 使用磷酸来提高 CC 活化反应中有问题的环戊酮底物的效率和区域选择性，以及 3)通过烯丙基环脱氢偶联将沙鲁坦直接转化为两性双萜。

  DOI：

  10.1002/anie.201915821
• 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 正丁基锂 、 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 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 194.5h， 生成 (5S,8R)-3,8-dimethyl-5-[6-methylhept-5-en-2-(R)-yl]-1-methoxy-5,6,7,8-tetrahydronaphthalene
  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

• Synthesis of Leubethanol derivatives and evaluation against Mycobacterium tuberculosis
  作者：Jonathan Perez-Meseguer、Esther del Olmo、Blanca Alanis-Garza、Ricardo Escarcena、Elvira Garza-González、Ricardo Salazar-Aranda、Arturo San Feliciano、Noemí Waksman de Torres

  DOI：10.1016/j.bmc.2012.04.059

  日期：2012.7

  Twenty-five derivatives of the natural diterpene leubethanol, including several potential pro-drugs, with changes in the functionality of the aliphatic chain or modifications of the phenolic group, were synthesized and tested in vitro by the MABA technique for their activity against the H37Rv strain of Mycobacterium tuberculosis. Several compounds showed antimycobacterial potencies similar to that of the lead compound and two of them displayed higher selectivity indexes. (C) 2012 Elsevier Ltd. All rights reserved.
• Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones
  作者：Si‐Hua Hou、Adriana Y. Prichina、Mengxi Zhang、Guangbin Dong

  DOI：10.1002/anie.201915821

  日期：2020.5.11

  The key step in these syntheses involve a Rh-catalyzed C-C/C-H activation cascade of 3-arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C-H amination of the tetralone substrate in the synthesis of (-)-microthecaline A, 2) the use of phosphoric

  为了展示催化 CC 活化对张力较小的底物的合成效用，这里描述了天然产物 (-)-microthecaline A、(-)-leubehanol、(+)-pseudopteroxodium、(+)- 的集体和简明合成。 seco-pseudopteroxilla、pseudopterosin AF 和 GJ 苷元以及 (+)-heritinin。这些合成的关键步骤涉及 Rh 催化的 3-芳基环戊酮的 CC/CH 活化级联，这提供了一种快速且对映选择性的途径来获取这些天然产物中存在的多取代四氢萘核心。其他重要特征包括 1) 在 (-)-微壳碱 A 合成中对四氢萘酮底物进行直接 CH 胺化，2) 使用磷酸来提高 CC 活化反应中有问题的环戊酮底物的效率和区域选择性，以及 3)通过烯丙基环脱氢偶联将沙鲁坦直接转化为两性双萜。
• 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.