1-[(3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-yl]-5-phenylmethoxypentan-2-one | 1333325-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1-[(3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-yl]-5-phenylmethoxypentan-2-one
• CAS: 1333325-35-1
• 化学式: C₄₀H₄₆O₅
• 分子量: 606.802
• InChiKey: JNHHLTKARUKUQX-UGLVAYHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-yl]-5-phenylmethoxypentan-2-one 在 盐酸 、 氢气 、 palladium(II) hydroxide 作用下， 反应 18.0h， 生成 (2R,3a'S,5'R)-5'-pentyl-3'3a',4,5,5',6'-hexahydro-3H-spiro[furan-2,2'pyrano[2,3,4-de]chromen]-8'-ol 、
  参考文献：
  名称：

  An Enantioselective Formal Synthesis of Berkelic Acid

  摘要：

  An enantioselective formal synthesis of berkelic acid is described. The key step Involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.

  DOI：

  10.1021/ol202265g
• 作为产物：
  描述：

  dimethyl 5-(benzyloxy)-2-oxopentylphosphonate 、 (3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-ol 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到1-[(3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-yl]-5-phenylmethoxypentan-2-one
  参考文献：
  名称：

  An Enantioselective Formal Synthesis of Berkelic Acid

  摘要：

  An enantioselective formal synthesis of berkelic acid is described. The key step Involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.

  DOI：

  10.1021/ol202265g

文献信息

• An Enantioselective Formal Synthesis of Berkelic Acid
  作者：Michael C. McLeod、Zoe E. Wilson、Margaret A. Brimble

  DOI：10.1021/ol202265g

  日期：2011.10.7

  An enantioselective formal synthesis of berkelic acid is described. The key step Involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.