(1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.0^2,4>undecan-7-ol | 145988-09-6

• 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: (1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.0^2,4>undecan-7-ol
• 英文别名: 7α,15-dihydroxyaromadendrane；(-)-15-hydroxy-epi-globulol；(1aR,4R,4aR,7R,7aS,7bS)-4-(hydroxymethyl)-1,1,7-trimethyl-2,3,4a,5,6,7,7a,7b-octahydro-1aH-cyclopropa[e]azulen-4-ol
• CAS: 145988-09-6
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: VVQCFCMDMCMZBG-RWXDJMAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.0^2,4>undecan-7-ol 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (-)-蓝桉醇
  参考文献：
  名称：

  Hydroxylation of Aromadendrane Derivatives by Mucor plumbeus†

  摘要：

  7α-羟基和7α,15-二羟基-芳香树脂烷被铅霉有效地在C-14位进行羟基化，同时保留相邻的环丙烷环。

  DOI：

  10.1039/a605991k
• 作为产物：
  描述：

  (1aR,4R,4aR,7R,7aS,7bS)-1,1,7-trimethyl-4-((phenylselanyl)methyl)decahydro-1H-cyclopropa[e]azulen-4-ol 在 ammonium peroxydisulfate 、 水 作用下， 以 乙腈 为溶剂， 以8%的产率得到(1S,2S,4R,7R,8R,11R)-3,3,11-trimethyl-7-hydroxymethyl-tricyclo<6.3.0.0^2,4>undecan-7-ol
  参考文献：
  名称：

  Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents

  摘要：

  Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)(2) with (NH4)(2)S2O8 at reflux in a 3:1 mixture of MeCN-H2O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.

  DOI：

  10.1080/10426500801900881

文献信息

• Microbial oxidation of tricyclic sesquiterpenoids containing a dimethylcyclopropane ring
  作者：Wolf-Rainer Abraham、Klaus Kieslich、Burkhard Stumpf、Ludger Ernst

  DOI：10.1016/s0031-9422(00)97521-6

  日期：1992.1

  Abstract Calarene was oxidized by Bacillus megaterium and Diplodia gossypina to give allylic calarenols and calarendiols in which either of the geminal methyl groups of the cyclopropane ring was hydroxylated. Globulol was hydroxylated faster and in higher yields than calarene by both strains. In the case of this compound, vicinal diols were formed and, again, either of the geminal methyl groups was

  摘要 Calarene 被巨大芽孢杆菌和棉双歧杆菌氧化，得到烯丙基的calarenols 和calarendiol，其中环丙烷环的双生甲基中的任何一个被羟基化。Globulol 被两种菌株羟基化得更快，产率也高于卡拉烯。在这种化合物的情况下，形成了邻二醇，并且再次氧化了任何一个孪生甲基。只有细菌菌株引起 9-羟基化。耻垢分枝杆菌以良好的产量生产 globulol-14-exo-14-oic 酸。在孪生甲基中，外向取向的甲基优先被所有测试的菌株攻击。形成的一些代谢物是已知天然产物的立体异构体。
• Hydroxylation of Aromadendrane Derivatives by Mucor plumbeus†
  作者：Ricardo Guillermo、James R. Hanson、Almaz Truneh

  DOI：10.1039/a605991k

  日期：——

  Both 7α-hydroxy- and 7α,15-dihydroxy-aromadendrane are efficiently hydroxylated by Mucor plumbeus at C-14 with retention of the adjacent cyclopropane ring.

  7α-羟基和7α,15-二羟基-芳香树脂烷被铅霉有效地在C-14位进行羟基化，同时保留相邻的环丙烷环。
• Diastereo and Enantioselective Synthesis of 1,2-Diols Promoted by Electrophilic Selenium Reagents
  作者：C. Santi、M. Tiecco、L. Testaferri、C. Tomassini、S. Santoro、G. Bizzoca

  DOI：10.1080/10426500801900881

  日期：2008.4.1

  Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)(2) with (NH4)(2)S2O8 at reflux in a 3:1 mixture of MeCN-H2O. Interestingly the reaction can be performed in "one pot" using a catalytic amount of diselenide affording the corresponding diols (5 and 6) with good yield and good level of diastereo- and enantioselectivity.