4-tert-butyl-1-(2'-phenylethyl)-1-cyclohexanol | 88279-04-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 4-tert-butyl-1-(2'-phenylethyl)-1-cyclohexanol
• 英文别名: 4-(tert-butyl)-1-phenethylcyclohexan-1-ol；Cyclohexanol, 4-(1,1-dimethylethyl)-1-(2-phenylethyl)-；4-tert-butyl-1-(2-phenylethyl)cyclohexan-1-ol
• CAS: 88279-04-3
• 化学式: C₁₈H₂₈O
• 分子量: 260.42
• InChiKey: CXOMIDLQXYSUGU-UHFFFAOYSA-N

物化性质

• 沸点：
  360.9±11.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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-叔丁基环己酮二苄基缩醛 在 palladium on activated charcoal 、 Lewis acid 氢气 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 4-tert-butyl-1-(2'-phenylethyl)-1-cyclohexanol
  参考文献：
  名称：

  烯醇甲硅烷基醚与环己酮缩醛之间的醛醇缩合反应中赤道选择性显着

  摘要：

  路易斯酸催化的烯醇甲硅烷基醚和取代的环己酮缩醛的醛醇缩合反应显示出比母体酮的反应明显更高的赤道侵蚀率。

  DOI：

  10.1039/c39830000796

文献信息

• Preparation of Samarium(II) Triflate and It Mediated Grignard-type Reaction. In Situ Formation and Reaction of New Organosamarium Reagents
  作者：Shin-ichi Fukuzawa、Teruhisa Tsuchimoto、Takeshi Kanai

  DOI：10.1246/cl.1994.1981

  日期：1994.11

  Samarium(II) triflate was readily prepared by the reaction of samarium(III) triflate with sec-butyllithium at room temperature in THF. Its reducing ability was examined by pinacol coupling of carbonyl compounds. Sm(OTf)2 mediated Grignard-type reaction in THF-HMPA effectively; alkylation and allylation of ketones or aldehydes by simple alkyl, allyl, and benzyl halides proceeded via organosamarium intermediates

  三氟甲磺酸钐 (II) 很容易通过三氟甲磺酸钐 (III) 与仲丁基锂在室温下在 THF 中反应制备。通过羰基化合物的频哪醇偶联来检测其还原能力。Sm(OTf)2在THF-HMPA中有效介导格氏型反应；通过有机钐中间体通过简单的烷基、烯丙基和苄基卤化物对酮或醛进行烷基化和烯丙基化。
• Cathodic Regioselective Coupling of Unactivated Aliphatic Ketones with Alkenes
  作者：Hongting Wu、Weihao Chen、Weijie Deng、Ling Yang、Xinling Li、Yunfei Hu、Yibiao Li、Lu Chen、Yubing Huang

  DOI：10.1021/acs.orglett.2c00314

  日期：2022.2.18

  A regioselective coupling of aliphatic ketones with alkenes has been realized by cathodic reduction. This reaction enables the formation of ketyl radicals and the activation of challenging alkenes under mild electrolysis conditions, providing an effective protocol for accessing diverse tertiary alcohols with substrate-dependent regioselectivity. The practicability of this reaction is demonstrated by

  已经通过阴极还原实现了脂肪族酮与烯烃的区域选择性偶联。该反应能够在温和的电解条件下形成酮基自由基并激活具有挑战性的烯烃，为获得具有底物依赖性区域选择性的多种叔醇提供了有效的方案。通过放大实验证明了该反应的实用性。通过对照实验证明了产物的氢源、烯丙基芳烃的迁移异构化和内烯烃的适用性。
• Samarium(II) Triflate as a New Reagent for the Grignard-Type Carbonyl Addition Reaction
  作者：Shin-ichi Fukuzawa、Keisuke Mutoh、Teruhisa Tsuchimoto、Tamejiro Hiyama

  DOI：10.1021/jo960260s

  日期：1996.1.1

  On treatment of a THF solution of Sm(OTf)(3) with 1 equiv of an organolithium or organomagnesium reagent-at ambient temperature, the purple or deep green solution of the divalent samarium triflate [Sm(OTf)(2)] was readily obtained. For this preparation, s-BuLi was the most effective as was evidenced by the reduction of a-phenylethyl iodide in the presence of HMPA. The Sm(OTf)(2) reagent mediated the Grignard-type reaction effectively in THF/HMPA; alkylation and allylation of ketones or aldehydes with alkyl, allyl, or benzyl halides proceeded via organosamarium intermediates. Diastereoselectivity of the samarium-Grignard reaction was examined using 2-methylcyclohexanone, 4-tert-butylcyclohexanone, and 2-phenylpropanal and was found to be higher in each case than that with SmI2. With 2-methylcyclohexanone, for example, Sm(OTf)(2) gave the greatest ratio of axial alcohol:equatorial alcohol = 99:1, and SmI2 gave a ratio of 91:9. Halides containing an ester or a silyl group were reactive in the Reformatsky- or Peterson-type reaction, respectively, using the Sm(OTf)(2) reagent.
• Ketone Coupling with Alkyl Iodides, Bromides, and Chlorides Using Thulium Diiodide:  A More Powerful Version of SmI₂(THF)<i>_x</i>/HMPA
  作者：William J. Evans、Nathan T. Allen

  DOI：10.1021/ja992951m

  日期：2000.3.1