(1R,2R)-2-((E)-3-phenylprop-1-en-1-yl)-1,2-dihydronaphthalen-1-ol | 1338601-56-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (1R,2R)-2-((E)-3-phenylprop-1-en-1-yl)-1,2-dihydronaphthalen-1-ol
• 英文别名: (1R,2R)-2-[(E)-3-phenylprop-1-enyl]-1,2-dihydronaphthalen-1-ol
• CAS: 1338601-56-1
• 化学式: C₁₉H₁₈O
• 分子量: 262.351
• InChiKey: GTVLGZOMVGLHHC-RDSSZPGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,2R)-2-((E)-3-phenylprop-1-en-1-yl)-1,2-dihydronaphthalen-1-ol 在 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 15.0h， 以92%的产率得到(1R,2R)-2-(3-phenylpropyl)-1,2,3,4-tetrahydronaphthalen-1-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x
• 作为产物：
  描述：

  1,4-epoxy-1,4-dihydronaphthalene 、 2,4,6-tris((E)-3-phenylprop-1-en-1-yl)-1,3,5,2,4,6-trioxatriborinane 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine 、 caesium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.0h， 生成 (1R,2R)-2-((E)-3-phenylprop-1-en-1-yl)-1,2-dihydronaphthalen-1-ol 、 (1S,2S)-2-((E)-3-phenylprop-1-en-1-yl)-1,2-dihydronaphthalen-1-ol
  参考文献：
  名称：

  Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes

  摘要：

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.

  DOI：

  10.1021/jo201781x

文献信息

• Diastereoselective Friedel–Crafts Alkylation of Hydronaphthalenes
  作者：Jennifer Tsoung、Katja Krämer、Adam Zajdlik、Clemence Liébert、Mark Lautens

  DOI：10.1021/jo201781x

  日期：2011.11.4

  An efficient and versatile synthesis of chiral tetralins has been developed using both inter- and intra-molecular Friedel Crafts alkylation as a key step. The readily available hydronaphthalene substrates were prepared via a highly enantioselective metal-catalyzed ring opening of meso-oxabicyclic alkenes followed by hydrogenation. A wide variety of complex tetracyclic compounds have been isolated with high levels of regio-, diastereo-, and enantioselectivity.