(4-(2-methoxynaphthalen-1-yl)phenanthren-3-yl)methanol | 1449041-08-0

• 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: (4-(2-methoxynaphthalen-1-yl)phenanthren-3-yl)methanol
• CAS: 1449041-08-0
• 化学式: C₂₆H₂₀O₂
• 分子量: 364.444
• InChiKey: WVSLMIMUPAHJJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.31
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (4-(2-methoxynaphthalen-1-yl)phenanthren-3-yl)methanol 在 三溴化硼 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 19.5h， 生成 12-Oxahexacyclo[12.12.0.02,11.03,8.017,26.020,25]hexacosa-1(14),2(11),3,5,7,9,15,17(26),18,20,22,24-dodecaene
  参考文献：
  名称：

  Synthesis of partially hydrogenated oxa[5] and oxa[6]helicenes from β-chlorovinylaldehydes

  摘要：

  Synthesis of partially hydrogenated oxa[5]helicenes is described starting from easily available beta-chlorovinylaldehydes. The short sequence involved a Suzuki-Miyaura type coupling between beta-chlorovinylaldehydes and arylboronic acids bearing ortho-methoxy groups. The presence of both the formyl and the methoxy groups allowed after reduction and demethylation respectively, the construction of the central dehydropyran ring. The molecular structure of the extended benzopyrene-based oxa[5]helicenes has been fully determined in solution and in the solid state. The strategy could be extended to oxa[6]helicene. Atroposelective Suzuki-Miyaura couplings were the key steps of the nonracemic preparation of oxa[5]helicenes. Ee observed are in good agreement with the theoretically calculated racemization barriers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.101
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以85%的产率得到(4-(2-methoxynaphthalen-1-yl)phenanthren-3-yl)methanol
  参考文献：
  名称：

  Synthesis of partially hydrogenated oxa[5] and oxa[6]helicenes from β-chlorovinylaldehydes

  摘要：

  Synthesis of partially hydrogenated oxa[5]helicenes is described starting from easily available beta-chlorovinylaldehydes. The short sequence involved a Suzuki-Miyaura type coupling between beta-chlorovinylaldehydes and arylboronic acids bearing ortho-methoxy groups. The presence of both the formyl and the methoxy groups allowed after reduction and demethylation respectively, the construction of the central dehydropyran ring. The molecular structure of the extended benzopyrene-based oxa[5]helicenes has been fully determined in solution and in the solid state. The strategy could be extended to oxa[6]helicene. Atroposelective Suzuki-Miyaura couplings were the key steps of the nonracemic preparation of oxa[5]helicenes. Ee observed are in good agreement with the theoretically calculated racemization barriers. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.101