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 | 1449041-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 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
• 英文别名: 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
• CAS: 1449041-09-1
• 化学式: C₂₅H₁₆O
• 分子量: 332.401
• InChiKey: OVGVKWDIHUFKJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.04
• 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：

  4-chloro-1,2-dihydrophenanthrene-3-carbaldehyde 在 2-双环己基膦-2',6'-二甲氧基联苯 、 sodium tetrahydroborate 、 palladium diacetate 、 三溴化硼 、 cesium fluoride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 甲苯 为溶剂， 反应 24.5h， 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

文献信息

• Synthesis of partially hydrogenated oxa[5] and oxa[6]helicenes from β-chlorovinylaldehydes
  作者：Alexandre Requet、Amel Souibgui、Grégory Pieters、Sabrina Ferhi、Alicia Letaieff、Abel Carlin-Sinclair、Sylvain Marque、Jérome Marrot、Béchir Ben Hassine、Anne Gaucher、Damien Prim

  DOI：10.1016/j.tetlet.2013.06.101

  日期：2013.8

  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.