5,11,17,23-tetra(tert-butyl)-25,27-dihydroxy-26,28-bis(2-naphthylmethoxy)calix[4]arene | 321996-39-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5,11,17,23-tetra(tert-butyl)-25,27-dihydroxy-26,28-bis(2-naphthylmethoxy)calix[4]arene
• 英文别名: 5,11,17,23-Tetratert-butyl-26,28-bis(naphthalen-2-ylmethoxy)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,27-diol
• CAS: 321996-39-8
• 化学式: C₆₆H₇₂O₄
• 分子量: 929.295
• InChiKey: HALWFVSHQKJYKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  19.1
• 重原子数：
  70
• 可旋转键数：
  10
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra(tert-butyl)-25,27-dihydroxy-26,28-bis(2-naphthylmethoxy)calix[4]arene 在 titanium(IV) chloride tetrahydrofuran 、 盐酸 、 水 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以100%的产率得到5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene
  参考文献：
  名称：

  Easy and Selective Method for the Synthesis of Various Mono-O-functionalized Calix[4]arenes: De-O-functionalization Using TiCl₄

  摘要：

  An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized

  DOI：

  10.1021/jo101319s
• 作为产物：
  描述：

  5,11,17,23-tetra-t-butyl-25,26,27,28-tetrahydroxycalix-4-arene 、 2-溴甲基萘 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以59%的产率得到5,11,17,23-tetra(tert-butyl)-25,27-dihydroxy-26,28-bis(2-naphthylmethoxy)calix[4]arene
  参考文献：
  名称：

  Stoikov; Khrustalev; Antipin, Doklady Chemistry, 2000, vol. 374, # 1-3, p. 179 - 182

  摘要：

  DOI：

文献信息

• Highly Regioselective Hydroformylation with Hemispherical Chelators
  作者：David Sémeril、Dominique Matt、Loïc Toupet

  DOI：10.1002/chem.200800747

  日期：2008.8.18

  straightforwardly provide chelate complexes in which the metal centre sits in a molecular pocket defined by two naphthyl planes related by the C(2) axis and the two apically situated R groups. Hydroformylation of octene with the L(Pr)/Rh system turned out to be highly regioselective, the linear-to-branched (l:b) aldehyde ratio reaching 58:1. The l:b ratio significantly increased when the propyl groups were replaced

  半球形二亚磷酸酯（R，R）-或（S，S）-5,11,17,23-四叔丁基-25,27-di（OR）-26,28-双（1,1'-双萘基2,2'-二氧杂磷酰氧基）杯[4]芳烃（R = OPr，OCH（2）Ph，OCH（2）-萘基，O-芴基; R = H，R'= OPr）（L（R ）），全部具有C（2）对称性，已从适当的二-O-烷基化杯[4]芳烃前体开始合成。在[Rh（acac）（CO）（2）]的存在下，这些配体直接提供螯合物，其中金属中心位于由两个与C（2）轴相关的萘平面和两个顶点所定义的分子袋中位于R组。L（Pr）/ Rh系统对辛烯的加氢甲酰化反应显示出高度的区域选择性，线性与支化（l：b）醛的比例达到58：1。当丙基被-CH（2）Ph（1：b = 80）或-CH（2）萘基（l：b = 100），即具有能够与顶端金属位点空间相互作用但不引起裂口开口的嵌套取代基，该裂口嵌套了催化中心。在苯乙烯
• Stoikov; Khrustalev; Antipin, Doklady Chemistry, 2000, vol. 374, # 1-3, p. 179 - 182
  作者：Stoikov、Khrustalev、Antipin、Konovalov

  DOI：——

  日期：——
• Substituent-Dependent Formation of Organotransition-Metal Bimetallic Calix[4]arene Inclusion Complexes
  作者：Ella Bukhaltsev、Israel Goldberg、Arkadi Vigalok

  DOI：10.1021/om049568x

  日期：2004.9.1

  Reaction of 1,3-di-O-substituted calixarene ligands with Et2Zn gives new organotransition-metal bimetallic calix[4]arene inclusion complexes when the substituent is larger than methyl. The resulting complexes show strong interactions between the incorporated organometallic fragment and the hydrophobic cavity of the calixarene group.
• ——
  作者：I. S. Antipin、I. I. Stoikov、A. A. Khrustalev、A. I. Konovalov

  DOI：10.1023/a:1015005502810

  日期：——

  A new type of macrocyclic receptor able to bind organic Substrates containing carboxy and carboxylate groups was designed on the basis of 1,3-disubstituted calix[4]arenes. A series of disubstitited calix[4]arenes were prepared in 60-80% yields by selective 1,3-alkylation of p-tert-butylcalix[4]arene. The compounds obtained were tested as carriers for DL-tartaric, glycolic, DL-amygdalic, and DL-glutamic acids through liquid membranes immobilized on a polymer matrix. The structural factors favorable for the transport of these hydrophilic substrates through lipophilic membranes were established.
• Easy and Selective Method for the Synthesis of Various Mono-<i>O</i>-functionalized Calix[4]arenes: De-<i>O</i>-functionalization Using TiCl₄
  作者：Joackim Bois、Jeff Espinas、Ulrich Darbost、Caroline Felix、Christian Duchamp、Denis Bouchu、Mostafa Taoufik、Isabelle Bonnamour

  DOI：10.1021/jo101319s

  日期：2010.11.19

  An efficient and selective method for the monofunctionalization of p-tert-butylcalix[4]arene is described A mono-de-O-functionalization of disubstituted p-tert-butylcalix[4]arenes using titanium tetrachloride was developed to synthesize a series of monosubstituted p-tert-butylcalix[4]arenes with the pendant functions being ethoxycarbonylmethyloxy, 3-ethoxycarbonylpropyloxy, cyanomethyloxy, 3-cyanopropyloxy, 4-bromobutyloxy, 3-hydroxypropyloxy, propyloxy, 2-methylpropyloxy, 3-butynyloxy, and 3-cyanopropyloxy groups The reaction mechanism of the formation of 5,11,17,23-tetra-tert-butyl-26,27,28-trihydroxy-25-(3-ethoxycarbonylpropyloxy) calix[4]arene was studied by H-1 NMR and GC/mass spectroscopy monitoring Reaction of TiCl4 with the disubstituted p-tert-butylcalix[4]arene produced the corresponding dioxocalix[4]arene titanium dichloride complex, which undergoes elimination of ethyl 4-chlorobutyrate, leading to a trioxocalix[4]arene titanium dichloride complex and to monosubstituted calix[4]arene after hydrolysis These two complexes were also synthesized, isolated, and fully characterized