phenyl (1R)-1-phenylethyl ether

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: phenyl (1R)-1-phenylethyl ether
• 英文别名: (R)-1-phenylethyl phenyl ether；(R)-(1-phenyloxyethyl)benzene；(R)-methylbenzyl phenyl ether；(R)-α-Phenylaethyl-phenyl-aether；[(1R)-1-phenoxyethyl]benzene
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: MMDVBQJVKNNYLU-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (S)-(-)-1-苯乙醇 在 正丁基锂 、 2,6-二甲基-2,5-环己二烯-1,4-二酮 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 phenyl (1R)-1-phenylethyl ether
  参考文献：
  名称：

  通过氧化-还原缩合制备烷基-芳基和醇和酚或二醇之间的对称或不对称二烷基醚的有效方法

  摘要：

  通过烷氧基二苯基膦（二苯基亚膦酸酯）（1）进行氧化还原缩合，由氯二苯基膦（2）和醇、2,6-二甲基-1,4-苯醌（3）原位生成，苯酚顺利进行，得到烷基芳基醚在中性条件下产量良好。以类似的方式，通过四氟-1,4-苯醌（荧苯胺）（4）、醇类和 1 由（ n) BuLi 处理的醇和 2. 该方法也适用于具有保留或反转构型的手性仲醇或叔醇的醚化。通过处理手性烷氧基二苯基膦和非手性醇得到反相醚，

  DOI：

  10.1021/ja0487877

文献信息

• Stereoselective synthesis of optically active phenyl ethers
  作者：Sadri A Said、Anne Fiksdahl、Per H.J Carlsen

  DOI：10.1016/s0040-4039(00)00872-8

  日期：2000.7

  1,2-naphthalenedisulfonimide of (S)-α-methylbenzylamine with phenol gave the corresponding α-methylbenzyl phenyl ether with 46% e.e. Synthesis of the authentic optically active phenyl ethers was accomplished under mild, neutral conditions by generating benzyne in the presence of optically active (R)-α-methylbenzyl alcohol. Benzyne was generated by reacting anthranilic acid with tert-butyl nitrite in

  反应的（1,2- naphthalenedisulfonimide小号）-α甲基苄基胺与苯酚给出了与46％对应的α甲基苄基苯基醚EE正宗光学活性的苯基醚的合成通过在存在产生苯炔温和，中性条件下完成（R）-α-甲基苄醇的合成。通过使邻氨基苯甲酸与亚硝酸叔丁酯在回流的单甘醇二甲醚中反应生成苯炔。
• Retentive Solvolysis. 16. Reinvestigation of the Retentive Phenolysis of 1-Phenylethyl Chloride. The Mechanism and the Structure of Ion Pair Intermediate
  作者：Tomomi Kinoshita、Takuya Ueno、Keizo Ikai、Masataka Fujiwara、Kunio Okamoto

  DOI：10.1246/bcsj.61.3273

  日期：1988.9

  chloride. The pattern C indicates that the first ion pair intermediate, not the second one, is nucleophilically attacked by solvent phenol molecule. The major products were the partially retained o-RC6H4OH, the partially inverted p-RC6H4OH, together with the partially retained ROPh. The same kp–kt pattern C has been observed for the competitive solvolysis of RCl in phenol–methanol (85:15 w/w), which produced

  对于 1-苯基乙基氯 (RCl) 在苯酚-苯 (1:1 w/w) 中的苯酚分解，已重新研究了添加苯胺对旋光 (kp) 和滴定速率常数 (kt) 的影响。相对于苯胺浓度的 kp-kt 图显示了模式 C，而不是我们实验室以前的结果 A。已经表明，由于忽略了由释放的氯化氢引起的逆反应，先前在较低苯胺浓度下的速率常数（包括没有苯胺的情况）被低估了。模式 C 表明第一个离子对中间体，而不是第二个，被溶剂苯酚分子亲核攻击。主要产物是部分保留的 o-RC6H4OH、部分转化的 p-RC6H4OH 以及部分保留的 ROPh。
• Ullmann CO coupling of sterically hindered secondary alcohols using excess amount of strongly coordinating monodentate ligands
  作者：Hayato Sugata、Tetsu Tsubogo、Yoshitaka Kino、Hiromi Uchiro

  DOI：10.1016/j.tetlet.2017.01.095

  日期：2017.3

  A new effective copper catalyzed C-O coupling reaction using excess amount of strongly coordinating monodentate ligands was successfully developed. Among the DMAP-type monodentate ligands, 4-pyrrolidinopyridine afforded the best results. The developed reaction is widely applicable for the synthesis of various hindered or acyclic secondary alkyl-aryl ethers. In this study, a novel and remarkable acceleration of the coupling reaction using excess amount of monodentate ligands was discovered. (C) 2017 Elsevier Ltd. All rights reserved.
• Formation of chiral aryl ethers from enantiopure amine or alcohol substrates
  作者：Sadri A. Said、Anne Fiksdahl

  DOI：10.1016/s0957-4166(01)00130-6

  日期：2001.4

  Three methods for the preparation of chiral aryl ethers are demonstrated. N,N-Disulfonylimide derivatives are used in the stereoselective formation of aryl ethers from chiral amines. Nucleophilic attack of aryloxide anions on the cyclic N,N-disulfonylimide derivative of (S)-1-phenylethylamine afforded the (R)-1-phenylethyl phenyl and 2-naphthyl ethers with 83-87 and 70-79% inversion of configuration, respectively. The results are compared with results from alternative methods for the preparation of homochiral aryl ethers from chiral alcohols with complete retention and inversion of configuration, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.