(5aS,11bR)-4,5,5a,6,7,11b-hexahydrophenanthro[4,3-b]-thiophene | 1338601-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: (5aS,11bR)-4,5,5a,6,7,11b-hexahydrophenanthro[4,3-b]-thiophene
• 英文别名: (5aS,11bR)-4,5,5a,6,7,11b-hexahydronaphtho[2,1-g][1]benzothiole
• CAS: 1338601-39-0
• 化学式: C₁₆H₁₆S
• 分子量: 240.369
• InChiKey: CHDMRCQBRNORBK-SWLSCSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  (1R,2S)-2-((E)-2-(thiophen-3-yl)vinyl)-1,2-dihydronaphthalen-1-ol 在 四氟硼酸-二乙醚络合物 、 sodium acetate 、 对甲苯磺酰肼 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 15.33h， 生成 (5aS,11bR)-4,5,5a,6,7,11b-hexahydrophenanthro[4,3-b]-thiophene
  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.