2,7,12-trimethoxy-3,8,13-trimethylthio-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene | 146453-27-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,7,12-trimethoxy-3,8,13-trimethylthio-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
• 英文别名: rac-2,7,12-trimethoxy-3,8,13-trimethylthio-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene；5,12,19-Trimethoxy-6,13,20-tris(methylsulfanyl)tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene；5,12,19-trimethoxy-6,13,20-tris(methylsulfanyl)tetracyclo[15.4.0.03,8.010,15]henicosa-1(21),3,5,7,10,12,14,17,19-nonaene
• CAS: 146453-27-2；146453-28-3；146397-76-4
• 化学式: C₂₇H₃₀O₃S₃
• 分子量: 498.731
• InChiKey: ALKRUJBRASBDGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,7,12-trimethoxy-3,8,13-trimethylthio-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene 在 Reney-Ni 、 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 生成 10,15-dihydro-5H-tribenzo[a,d,g][9]annulene-2,7,12-triol
  参考文献：
  名称：

  Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst

  摘要：

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.

  DOI：

  10.1021/jo050495g
• 作为产物：
  描述：

  3-methoxy-4-methylthiobenzyl alcohol 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以31%的产率得到2,7,12-trimethoxy-3,8,13-trimethylthio-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene
  参考文献：
  名称：

  Improved Synthesis of Functional CTVs and Cryptophanes Using Sc(OTf)₃ as Catalyst

  摘要：

  Functional cyclotriveratrylene (CTV) and cryptophane derivatives are synthesized in the presence of scandium triflate [Sc(OTf)(3)]. This route allows the preparation of new derivatives that could not be prepared or easily obtained by using the previously reported experimental procedures. With a catalytic amount of scandium triflate (1% mol), CTVs were obtained with yields similar to or higher than those reported previously in reactions run under strong acidic conditions. Cryptophanes were also synthesized in fairly good yields by performing the ring-closure step in the presence of a stoichiometric amount of Sc(OTf)(3). Interestingly, this novel approach strongly reduces the formation of side products and gives rise to novel functionalized molecules for the construction of supramolecular host-guest systems.

  DOI：

  10.1021/jo050495g

文献信息

• Generation of Stereocenters Around a C3-Symmetric Cyclotriveratrylene Crown
  作者：Julien Sansévérino、Emmanuel Aubert、Enrique Espinosa、Jean-Claude Chambron

  DOI：10.1002/ejoc.201101780

  日期：2012.4

  oxidation of racemic methylthio-substituted C3-symmetric cyclotriveratrylene (CTV) 2 produces the corresponding trisulfoxides 3 as follows. Oxidation with m-chloroperoxybenzoic acid (m-CPBA) in dichloromethane leads to the formation of a distribution of the four possible diastereomers that is relatively close to the statistical outcome, in which the C3-symmetric stereoisomers are the minor species. In

  外消旋甲硫基取代的 C3-对称环三戊四烯 (CTV) 2 的氧化产生如下相应的三亚砜 3。在二氯甲烷中用间氯过氧苯甲酸 (m-CPBA) 氧化导致形成四种可能的非对映异构体的分布，该分布与统计结果相对接近，其中 C3 对称立体异构体是次要物质。相比之下，室温下四氯化碳中的光学活性戴维斯试剂 [恶氮丙啶 (+)-4] 导致偏向 (73 %) 分布，有利于 3 的 C3 对称 MRRR/PSSS 非对映异构体，具有 56 % ee (PSSS根据戴维斯模型的对映异构体）。有趣的是，当氧化反应在甲苯中回流时，
• Sulfur-Incorporating Cyclotriveratrylene Analogues: The Synthesis of Cyclotrithioguaiacylene
  作者：Julien Sanseverino、Jean-Claude Chambron、Emmanuel Aubert、Enrique Espinosa

  DOI：10.1021/jo102324u

  日期：2011.3.18

  Cyclotriguaiacylene 1 is the universal precursor of cryptophanes, and represents an important intermediate for the preparation of functionalized cavitands of the cyclotriveratrylene family. Its thio analogue (cyclotrithioguaiacylene 3) was synthesized by two different routes, involving either the Newman-Kwart or the Pummerer rearrangement. The latter, performed starting from a trisulfoxide precursor, produced a purer compound in higher overall yield.