4-bromo-6-tert-butylsalicyl alcohol | 934477-14-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-bromo-6-tert-butylsalicyl alcohol
• 英文别名: 4-Bromo-2-tert-butyl-6-(hydroxymethyl)phenol
• CAS: 934477-14-2
• 化学式: C₁₁H₁₅BrO₂
• 分子量: 259.143
• InChiKey: JBXYDTNLEFNIOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  4-bromo-6-tert-butylsalicyl alcohol 在 三溴化磷 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 32.0h， 生成 C₃₀H₄₂Br₂N₂O₂
  参考文献：
  名称：

  Iron(iii)–salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

  摘要：

  手性铁(III)–salan复合物催化了β-酮酯和N-Boc氧杂环戊烯的高度对映选择性α-氟化和α-羟基化反应，在温和的反应条件下获得相应产物，产率高，对映体过量值良好至优异。

  DOI：

  10.1039/c4cc01631a
• 作为产物：
  描述：

  2-叔丁基苯酚 在 2,6-二甲基吡啶 、 sodium tetrahydroborate 、 溴 、 四氯化锡 、 溶剂黄146 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 14.83h， 生成 4-bromo-6-tert-butylsalicyl alcohol
  参考文献：
  名称：

  Iron(iii)–salan complexes catalysed highly enantioselective fluorination and hydroxylation of β-keto esters and N-Boc oxindoles

  摘要：

  手性铁(III)–salan复合物催化了β-酮酯和N-Boc氧杂环戊烯的高度对映选择性α-氟化和α-羟基化反应，在温和的反应条件下获得相应产物，产率高，对映体过量值良好至优异。

  DOI：

  10.1039/c4cc01631a

文献信息

• Mechanism of the Polymerization of <i>rac</i>-Lactide by Fast Zinc Alkoxide Catalysts
  作者：Daniel E. Stasiw、Anna M. Luke、Tomer Rosen、Aaron B. League、Mukunda Mandal、Benjamin D. Neisen、Christopher J. Cramer、Moshe Kol、William B. Tolman

  DOI：10.1021/acs.inorgchem.7b02544

  日期：2017.11.20

  of the ligand framework influences polymerization rate, selectivity, and control. After determination that zinc-ethyl precatalysts required 24 h of reaction with benzyl alcohol to convert to active alkoxide complexes, the subsequently formed species proved to be active and fairly selective, polymerizing up to 300 equiv of rac-LA in 6–10 min while yielding isotactic (Pm = 0.72–0.78) polylactide (PLA)

  使用L X Zn催化剂（L X =在结合的酚盐供体上具有可变对位取代基X的酚盐，胺和吡啶供体的配体）进行rac-丙交酯（rac -LA）的开环酯交换聚合（ROTEP）2，Br，t-Bu，OMe）是通过动力学实验和密度泛函理论进行评估的，目的是确定配体骨架的电子调节如何影响聚合速率，选择性和控制力。在确定锌-乙基预催化剂需要与苄醇反应24小时才能转化为活性醇盐络合物后，随后形成的物质被证明具有活性和相当的选择性，可在6-10分钟内聚合多达300当量的rac- LA，同时产生低分散度的等规（P m = 0.72-0.78）聚丙交酯（PLA）：Đ = 1.06-1.17。与以前的铝催化剂工作相比，铝催化剂的配体取代基的电子效应显着（Hammettρ= + 1.2-1.4），与之相反，L X锌系统表现出的影响要小得多（ρ= +0.3）。密度泛函计算揭示了引发和传播步骤的细节，从而使人们能够深入了解X的同一性和速率的不敏感性。
• 5-(1-Acetoxyvinyl)-<i>cyclo</i>Saligenyl-2′,3′-dideoxy-2′,3′- didehydrothymidine Monophosphates, a Second Type of New, Enzymatically Activated <i>cyclo</i>Saligenyl Pronucleotides
  作者：Nicolas Gisch、Florian Pertenbreiter、Jan Balzarini、Chris Meier

  DOI：10.1021/jm801197f

  日期：2008.12.25

  In our attempt to further develop the cycloSal pronucleotide concept, we report oil 5-(1-acetoxyvinyl)-cycloSal-d4TMPs as a new type of enzyme-activated pronucleotides. These compounds were converted into 5-acetyl-cycloSal-d4TMPs by (carboxy)esterase cleavage inside the cells. The enzymatic reaction led to the formation of a strong electron-withdrawing substituent that strongly accelerates the chemical hydrolysis of the cycloSal nucleotide to give d4TMP. For some cycloSal-d4TMPs a separation into the diastereomers was achieved. The absolute configuration was assigned by correlation of circular dichroism spectra with similar compounds. Most of the compounds showed complete retention of antiviral activity in TK-deficient CEM/TK- cells, which proves the TK-bypass potential of this approach. Interestingly, (S-p)-isomers of cycloSal phosphate triesters showed better antiviral activity in HIV-2-infected thymidine-kinase deficient CEM/TK- cells than their (R-p)-counterparts.
• Enzymatically Activated <i>cyclo</i>Sal-d4T-monophosphates:  The Third Generation of <i>cyclo</i>Sal-Pronucleotides
  作者：Nicolas Gisch、Jan Balzarini、Chris Meier

  DOI：10.1021/jm0613267

  日期：2007.4.1

  The third generation of cycloSal-pronucleotides, 5-diacetoxymethyl-cycloSal-d4T-monophosphates (5-di-AM-cycloSal-d4TMPs), is reported as a new class of "lock-in"-modified cycloSal-pronucleotides. These compounds bear an esterase-cleavable geminal dicarboxylate (acylal) attached to the aromatic ring of the saligenyl unit. The conversion into a strong acceptor group (aldehyde) leads to a strong decrease in hydrolytic stability. As a consequence, a fast release of a nucleoside monophosphate (i.e., d4TMP) follows. The concept of this enzymatic activation is proven by hydrolysis studies in phosphate buffer, cell extracts, and human serum. These investigations showed the conversion of the acylal group into a polar aldehyde by enzymatic cleavage. Besides, antiviral activities against HIV are presented.