双(2-异丙基苯基)甲醇 | 22679-66-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 双(2-异丙基苯基)甲醇
• 英文名称: bis(2-isopropylphenyl)methanol
• 英文别名: bis(o-isopropylphenyl)methanol；2,2'-Diisopropyl-benzhydrol
• CAS: 22679-66-9
• 化学式: C₁₉H₂₄O
• 分子量: 268.399
• InChiKey: WAUMEKIWETXUQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  20.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  双(2-异丙基苯基)甲醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以3.20 g的产率得到o,o'-diisopropylbenzophenone
  参考文献：
  名称：

  Stereomutations of Two-Bladed Propeller Derivatives:  Ortho-Substituted Diaryl Ethylene and Diaryl Ketone

  摘要：

  DIAGRAMStereochemical analysis, supported by ab initio computations, predicts the existence of three possible stable helical conformers for o,o'-diisopropyl-1,1'-diphenylethylene (1) and o,o'-diisopropylbenzophenone (2). At low temperature the NMR spectra of 1 showed distinct sets of signals for these conformers, thus allowing the measurement of the three barriers involved in the related stereomutation processes to be obtained (DeltaG(double dagger) = 6.45, 4.65, and less than or equal to 4.0 kcal mol(-1)). The NMR spectra also indicate that the asymmetric conformer (C-1 point group) is the most stable one in solution, as anticipated by calculations. X-ray diffraction confirmed that this structure is that adopted in the crystalline state. On the other hand, o,o'-diisopropylbenzophenone (2) is predicted by calculations to exist essentially as a C-2-type conformer, a result that was confirmed by the low-temperature NMR spectra. The interconversion barrier for the enantiomeric forms of this conformer was also measured (DeltaG(double dagger) = 6.35 kcal mol(-1)).

  DOI：

  10.1021/jo0483926
• 作为产物：
  描述：

  1-溴-2-异丙基苯 、 异丙基苯甲醛 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 生成 双(2-异丙基苯基)甲醇
  参考文献：
  名称：

  Stereomutations of Two-Bladed Propeller Derivatives:  Ortho-Substituted Diaryl Ethylene and Diaryl Ketone

  摘要：

  DIAGRAMStereochemical analysis, supported by ab initio computations, predicts the existence of three possible stable helical conformers for o,o'-diisopropyl-1,1'-diphenylethylene (1) and o,o'-diisopropylbenzophenone (2). At low temperature the NMR spectra of 1 showed distinct sets of signals for these conformers, thus allowing the measurement of the three barriers involved in the related stereomutation processes to be obtained (DeltaG(double dagger) = 6.45, 4.65, and less than or equal to 4.0 kcal mol(-1)). The NMR spectra also indicate that the asymmetric conformer (C-1 point group) is the most stable one in solution, as anticipated by calculations. X-ray diffraction confirmed that this structure is that adopted in the crystalline state. On the other hand, o,o'-diisopropylbenzophenone (2) is predicted by calculations to exist essentially as a C-2-type conformer, a result that was confirmed by the low-temperature NMR spectra. The interconversion barrier for the enantiomeric forms of this conformer was also measured (DeltaG(double dagger) = 6.35 kcal mol(-1)).

  DOI：

  10.1021/jo0483926

文献信息

• Catalytic Enantioselective Pictet–Spengler Reaction of α‐Ketoamides Catalyzed by a Single H‐Bond Donor Organocatalyst
  作者：Rémi Andres、Qian Wang、Jieping Zhu

  DOI：10.1002/anie.202201788

  日期：2022.5.2

  A simple prolinamide bearing a single H-bond donor urea function catalyzes the Pictet–Spengler reaction between tryptamines and α-ketoamides to afford 1,1-disubstituted tetrahydro-β-carbolines in excellent yields and enantiomeric excesses.

  带有单一氢键供体尿素功能的简单脯氨酰胺可催化色胺和 α-酮酰胺之间的 Pictet-Spengler 反应，以优异的产率和对映体过量提供 1,1-二取代的四氢-β-咔啉。
• Novel α-Amino Acid-Based Hydroxamic Acid Ligands for Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols
  作者：Yujiro Hoshino、Hisashi Yamamoto

  DOI：10.1021/ja002602o

  日期：2000.10.1
• De Winter; Nauta, European Journal of Medicinal Chemistry, 1977, vol. 12, # 2, p. 125 - 130
  作者：De Winter、Nauta

  DOI：——

  日期：——
• Fleurke,K.H. et al., Recueil des Travaux Chimiques des Pays-Bas, 1962, vol. 81, p. 93 - 101
  作者：Fleurke,K.H. et al.

  DOI：——

  日期：——