(S)-1-苯乙基苯基醚 | 53521-22-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (S)-1-苯乙基苯基醚
• 英文名称: (S)-1-phenylethyl phenyl ether
• 英文别名: phenyl-((S)-1-phenyl-ethyl)-ether；Phenyl-((S)-1-phenyl-aethyl)-aether；(+)-α-Phenethyl-phenyl-ether；[(1S)-1-phenoxyethyl]benzene
• CAS: 53521-22-5
• 化学式: C₁₄H₁₄O
• 分子量: 198.265
• InChiKey: MMDVBQJVKNNYLU-LBPRGKRZSA-N

物化性质

• 沸点：
  291.4±9.0 °C(Predicted)
• 密度：
  1.035±0.06 g/cm3(Predicted)

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：

  (R)-(+)-1-苯基乙醇 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-1-苯乙基苯基醚
  参考文献：
  名称：

  Formation of chiral aryl ethers from enantiopure amine or alcohol substrates

  摘要：

  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.

  DOI：

  10.1016/s0957-4166(01)00130-6

文献信息

• 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。
• The Stereochemistry of Aromatic Alkylations. II. The Thermal Rearrangement of Alkyl Aryl Ethers¹
  作者：Harold Hart、Herbert S. Eleuterio

  DOI：10.1021/ja01631a055

  日期：1954.1
• 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.