(S)-(4-叔丁基苯基)(苯基)甲醇 | 1013121-19-1

• 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: (S)-(4-叔丁基苯基)(苯基)甲醇
• 英文名称: (S)-(4-tert-butylphenyl)(phenyl)methanol
• 英文别名: (S)-(4-t-butylphenyl)(phenyl)methanol；(S)-(4-tert-butylphenyl)-phenylmethanol
• CAS: 1013121-19-1
• 化学式: C₁₇H₂₀O
• 分子量: 240.345
• InChiKey: RIXWZJSPMCRTGU-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  4-叔丁基苯甲酮 在 五羰基溴化锰(I) 、 氢气 、 potassium carbonate 、 (S_c,R_p)-N-[2-dimethylaminopyridine-6-methyl]-1-(2-bis[4-methoxy-3,5-dimethylphenyl]phosphino)ferrocenylethylamine 作用下， 以 乙醇 为溶剂， 50.0 ℃ 、5.0 MPa 条件下， 以36%的产率得到
  参考文献：
  名称：

  锰催化环酮对映选择性氢化的面配位 P,N,N 配体的合理设计

  摘要：

  Mn催化剂经过合理的重新设计，可以排斥sp 3杂化取代基，同时吸引sp 2取代基，从而实现环酮的对映选择性氢化。 DFT 计算能够对一系列底物的对映控制水平进行可靠预测。

  DOI：

  10.1002/anie.202212479

文献信息

• Bio-inspired asymmetric aldehyde arylations catalyzed by rhodium-cyclodextrin self-inclusion complexes
  作者：Susumu Tsuda、Kaoru Asahi、Ryota Takahashi、Hiroki Yamauchi、Ryoji Ueda、Takanori Iwasaki、Shin-ichi Fujiwara、Nobuaki Kambe

  DOI：10.1039/d1ob02014e

  日期：——

  conditions, with enantiomeric excesses of up to 96% observed. Kinetic and competition experiments revealed that self-inclusion of the Rh complex contributes to the high enantioselectivity and reactivity achieved by this catalytic system. Thus, this bio-inspired self-inclusion strategy is promising for the development of highly enantioselective and reactive transition-metal catalysts for asymmetric carbon–carbon

  过渡金属催化剂是碳-碳键形成反应的有力工具，使用天然酶难以实现。通过主客体相互作用表现出固有选择性和反应性的酶激发了人们对将酶促行为纳入高效生产对映体纯化合物的过渡金属催化系统的广泛兴趣。然而，很少报道具有高度对映选择性和反应性的仿生过渡金属催化剂。在这项研究中，我们将 γ-环糊精-咪唑鎓盐应用于铑催化的醛的不对称芳基化。该方法表现出广泛的底物范围，并且在优化的条件下以优异的产率获得了相应的芳基甲醇，观察到对映体过量高达 96%。动力学和竞争实验表明，Rh 复合物的自包含有助于该催化系统实现的高对映选择性和反应性。因此，这种受生物启发的自包含策略有望用于开发用于不对称碳-碳键形成的高对映选择性和反应性过渡金属催化剂。
• Design and Synthesis of Tunable Chiral 2,2′‐Bipyridine Ligands: Application to the Enantioselective Nickel‐Catalyzed Reductive Arylation of Aldehydes
  作者：Shuai Zhang、Saima Perveen、Yizhao Ouyang、Liang Xu、Tao Yu、Min Zhao、Linghua Wang、Peidong Song、Pengfei Li

  DOI：10.1002/anie.202117843

  日期：2022.5.9

  A tunable chiral 2,2′-bipyridine scaffold SBpy was rationally designed and enabled a general and highly enantioselective Ni-catalyzed addition of aryl halides to aldehydes. This approach is more step-economic than conventional strategies and allowed the preparation of various diaryl carbinols without the need to use preformed metallic reagents.

  合理设计了一种可调节的手性 2,2'-联吡啶支架 SBpy，并能够在 Ni 催化下将芳基卤化物与醛类进行通用且高度对映选择性的加成。这种方法比传统策略更经济，并且无需使用预制金属试剂即可制备各种二芳基甲醇。
• 一种手性2,2’-联吡啶配体及其制备方法和应用
  申请人：西安交通大学

  公开号：CN114014869B

  公开（公告）日：2023-03-24

  本发明提供一种手性2,2’‑联吡啶配体及其制备方法和应用，手性2,2’‑联吡啶配体简式如式(1)或式(1’)所示，
• Nickel‐Catalyzed Enantioselective Carbonyl Addition of Aryl Chlorides and Bromides to Aldehydes
  作者：Mingjie Jiang、Limei Yu、Chenhui Zou、Hao Yuan、Minghui Xu、Bin Chen、Ping Hu、Bi‐Qin Wang、Peng Cao

  DOI：10.1002/chem.202401591

  日期：2024.8.22

  cyanobis(oxazoline) as chiral ligands and Mn as reductant. Aryl and heteroaryl bromides react with phenyl aldehyde to produce dibenzyl alcohols in 16–99 % yields with 53–92 % ees. Morever, phenyl chloride with aryl, heteroaryl and alkyl aldehydes synthesize dibenzyl alcohols in high yields with moderate enantioselectivities.

  以氰基双(恶唑啉)为手性配体，Mn为还原剂，研究了镍催化芳基卤化物与醛的对映选择性加成反应。芳基溴和杂芳基溴与苯醛反应生成二苄醇，产率 16-99%，ee 53-92%。此外，苯氯与芳基、杂芳基和烷基醛可以高产率合成具有中等对映选择性的二苄醇。
• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.