4,4-dimethyl-2-phenyl-2-pentanol | 96226-11-8

• 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: 4,4-dimethyl-2-phenyl-2-pentanol
• 英文别名: 4,4-Dimethyl-2-phenylpentan-2-ol
• CAS: 96226-11-8
• 化学式: C₁₃H₂₀O
• 分子量: 192.301
• InChiKey: DAYWTHUMKWXKAA-UHFFFAOYSA-N

物化性质

• 沸点：
  224.3±8.0 °C(Predicted)
• 密度：
  0.946±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2-phenyl-2-pentanol 在 盐酸 作用下， 以 正戊烷 为溶剂， 生成 (2-Chloro-4,4-dimethylpentan-2-yl)benzene
  参考文献：
  名称：

  Solvolysis of 2-Aryl-2-chloro-4,4-dimethylpentanes. Confirmation of Validity of Brown−Okamoto σ⁺ Constants

  摘要：

  Specific rate constants of solvolysis in 90% aqueous acetone have been determined at 25 degrees C for 10 2-aryl-2-chloro-4,4-dimethylpentanes (3) having a substituent p-cycPr, p-Me, m-Me, p-F, (H), p-Cl, m-Cl, m-CF3, p-CF3, or p-NO2. The Hammett-Brown relation is satisfactorily Linear (r = 0.999) with pi of -4.51, showing that Brown-Okamoto sigma(+) values based on the solvolysis of the cumyl chloride system 1 are widely usable for the substrates solvolyzing without appreciable nucleophilic solvent participation. Solvolysis of 3 having 3,5-Cl-2 or 3,5-(CF3)(2) substituents suggests the use of sigma(+) values of +0.740 and +0.982 instead of respective 2 sigma(m)(+) values of +0.798 and +1.040. The large negative rho(+) values in TFE of -5.91 and -5.63 for 1 and 3, respectively, reflect decreased nucleophilic (or Br phi nsted base type) solvation. Comparison of solvolysis rates of 1 with 3, both having m-Cl, p-CFB, or 3,5-(CF3)(2) substituents, in aqueous ethanol, aqueous acetone, TFE, and TFE-EtOH suggests that nucleophilic intervention by solvent in the cumyl system increases as the intermediate carbocation becomes more electron-demanding.

  DOI：

  10.1021/jo9821067
• 作为产物：
  描述：

  2-(4,4-dimethyl-2-phenylpentan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 在 sodium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 12.08h， 以90%的产率得到4,4-dimethyl-2-phenyl-2-pentanol
  参考文献：
  名称：

  1,2‐Dialkylation of 1,1‐Arylboryl Alkenes Via Borata‐Alkene Intermediate

  摘要：

  AbstractWe describe here the conjugate addition of tert‐butyllithium to vinyl systems of boronic esters to generate a borata‐alkene intermediate, followed by a sequential SN2 reaction with alkyl halides, at room temperature. We envisioned this goal through engaged C(sp3) chemical entities avoiding metal catalysts, additives, radical initiators or specific irradiation. This reaction guarantees that the new tetrasubstituted carbon formed retains all the C atoms from the three starting materials involved in the assembly.magnified image

  DOI：

  10.1002/adsc.202200154

文献信息

• Multicomponent Oxyalkylation of Styrenes Enabled by Hydrogen‐Bond‐Assisted Photoinduced Electron Transfer
  作者：Adrian Tlahuext‐Aca、R. Aleyda Garza‐Sanchez、Frank Glorius

  DOI：10.1002/anie.201700049

  日期：2017.3.20

  Herein, we disclose a strategy for the activation of N‐(acyloxy)phthalimides towards photoinduced electron transfer through hydrogen bonding. This activation mode enables efficient access to C(sp3)‐centered radicals upon decarboxylation from bench‐stable and readily available substrates. Moreover, we demonstrate that the formed alkyl radicals can be successfully employed in a novel redox‐neutral method

  在这里，我们公开了一种通过氢键使N-（酰氧基）邻苯二甲酰亚胺向光诱导电子转移的活化策略。这种活化模式可以使从稳定的和易于获得的底物中脱羧，从而有效地获得以C（sp 3）为中心的自由基。此外，我们证明了所形成的烷基可以成功地用于新型氧化还原中性方法中，从而跨苯乙烯部分构建sp 3 -sp 3键，从而可以直接使用复杂的醇和醚骨架。
• Air-Assisted Addition of Grignard Reagents to Olefins. A Simple Protocol for a Three-Component Coupling Process Yielding Alcohols
  作者：Youhei Nobe、Kyohei Arayama、Hirokazu Urabe

  DOI：10.1021/ja055732b

  日期：2005.12.1

  example, (trimethylsilyl)methylmagnesium chloride and alpha-methylstyrene in ether at room temperature under dry air directly furnished 2-phenyl-4-(trimethylsilyl)-2-butanol in good yield. As the Grignard addition to olefins under argon with rigorous exclusion of O2 did not proceed at all, the above reaction should involve a radical mechanism: an alkyl radical generated by the aerial oxidation of the

  甲硅烷基甲基、叔烷基、烯基和芳基格氏试剂在空气气氛下与烯烃（如苯乙烯、共轭二烯和烯炔）发生分子间加成反应，得到同系醇。例如，(三甲基甲硅烷基)甲基氯化镁和α-甲基苯乙烯在室温干燥空气中的醚中直接以良好的收率提供2-苯基-4-(三甲基甲硅烷基)-2-丁醇。由于在严格排除 O2 的氩气下与烯烃的格氏加成根本没有进行，上述反应应该涉及自由基机制：格氏试剂空气氧化产生的烷基自由基加成到烯烃上，然后进行氧化。还公开了这种转化的代表性实例，其中获得了具有良好至极好非对映选择性或区域选择性的产物。
• Nuclear magnetic resonance studies of structure and hindered rotation in tertiary benzylic metal compounds
  作者：Gideon. Fraenkel、John G. Russell、Ying-Hsueh. Chen

  DOI：10.1021/ja00791a024

  日期：1973.5
• 1,2‐Dialkylation of 1,1‐Arylboryl Alkenes Via Borata‐Alkene Intermediate
  作者：Sara González、Oriol Salvado、Elena Fernández

  DOI：10.1002/adsc.202200154

  日期：2022.5.17

  AbstractWe describe here the conjugate addition of tert‐butyllithium to vinyl systems of boronic esters to generate a borata‐alkene intermediate, followed by a sequential SN2 reaction with alkyl halides, at room temperature. We envisioned this goal through engaged C(sp3) chemical entities avoiding metal catalysts, additives, radical initiators or specific irradiation. This reaction guarantees that the new tetrasubstituted carbon formed retains all the C atoms from the three starting materials involved in the assembly.magnified image
• Solvolysis of 2-Aryl-2-chloro-4,4-dimethylpentanes. Confirmation of Validity of Brown−Okamoto σ⁺ Constants
  作者：Ken'ichi Takeuchi、Masaaki Takasuka、Yasushi Ohga、Takao Okazaki

  DOI：10.1021/jo9821067

  日期：1999.4.1

  Specific rate constants of solvolysis in 90% aqueous acetone have been determined at 25 degrees C for 10 2-aryl-2-chloro-4,4-dimethylpentanes (3) having a substituent p-cycPr, p-Me, m-Me, p-F, (H), p-Cl, m-Cl, m-CF3, p-CF3, or p-NO2. The Hammett-Brown relation is satisfactorily Linear (r = 0.999) with pi of -4.51, showing that Brown-Okamoto sigma(+) values based on the solvolysis of the cumyl chloride system 1 are widely usable for the substrates solvolyzing without appreciable nucleophilic solvent participation. Solvolysis of 3 having 3,5-Cl-2 or 3,5-(CF3)(2) substituents suggests the use of sigma(+) values of +0.740 and +0.982 instead of respective 2 sigma(m)(+) values of +0.798 and +1.040. The large negative rho(+) values in TFE of -5.91 and -5.63 for 1 and 3, respectively, reflect decreased nucleophilic (or Br phi nsted base type) solvation. Comparison of solvolysis rates of 1 with 3, both having m-Cl, p-CFB, or 3,5-(CF3)(2) substituents, in aqueous ethanol, aqueous acetone, TFE, and TFE-EtOH suggests that nucleophilic intervention by solvent in the cumyl system increases as the intermediate carbocation becomes more electron-demanding.