(R)-(+)-1-phenyl-3-(2-naphthoxy)-1-butene | 223510-73-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-(+)-1-phenyl-3-(2-naphthoxy)-1-butene
• 英文别名: 2-[(E,2R)-4-phenylbut-3-en-2-yl]oxynaphthalene
• CAS: 223510-73-4
• 化学式: C₂₀H₁₈O
• 分子量: 274.362
• InChiKey: JXRVNFYSGJOBFR-LPQFERQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-1-phenyl-3-(2-naphthoxy)-1-butene 在 2 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 以70%的产率得到(E)-1-(4-phenylbut-3-en-2-yl) naphthalen-2-ol
  参考文献：
  名称：

  Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics

  摘要：

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.

  DOI：

  10.1021/jo982178y
• 作为产物：
  描述：

  methyl (R)-[(E)-1-methyl-3-phenyl-2-propenyl] carbonate 、 2-萘酚 在 Pd₂(dpa)3 、 1,4-双(二苯基膦)丁烷 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到(R)-(+)-1-phenyl-3-(2-naphthoxy)-1-butene
  参考文献：
  名称：

  Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics

  摘要：

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.

  DOI：

  10.1021/jo982178y

文献信息

• Molybdenum(II)-Catalyzed Allylation of Electron-Rich Aromatics and Heteroaromatics
  作者：Andrei V. Malkov、Stuart L. Davis、Ian R. Baxendale、William L. Mitchell、Pavel Kočovský

  DOI：10.1021/jo982178y

  日期：1999.4.1

  The stable, readily available molybdenum(II) complexes [Mo(CO)(4)Br-2](2) (B) and Mo(CO)(3)(MeCN)(2)(SnCl3)Cl (C) have been found to catalyze C-C bond-forming allylic substitution with electron-rich aromatics (e.g., 15 + PhOMe --> 62) and heteroaromatics (e.g., 15 + 36 --> 88) as nucleophiles under mild conditions (room temperature, 30 min-3 h). Remarkable is the para-selectivity for anisole, whereas phenol tends to favor ortho-substitution in certain instances. Mechanistic and stereochemical experiments are indicative of Lewis-acid catalysis rather than a metal template-controlled process.