(-)-1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] | 339266-71-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol]
• 英文别名: (1R,3R,5R)-1-[[(1R,3R,5R)-3-hydroxy-8-oxabicyclo[3.2.1]oct-6-en-1-yl]methyl]-8-oxabicyclo[3.2.1]oct-6-en-3-ol
• CAS: 339266-71-6
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: OIGBACZWYSIEQN-PEZGRIKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] 在 吡啶 、 4-二甲氨基吡啶 、 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 1,1'-methylenedi[(3S,3'S,4R,4'R,6S,6'S)-3-chlorocyclohept-1-en-4,6-diyl] tetrakis(p-methoxybenzoate)
  参考文献：
  名称：

  Synthesis of 1,1′-methylenedi[(1 R ,1′ R ,3 R ,3′ R ,5 R ,5′ R )-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketides

  摘要：

  Racemic 1,1'-methylene[(1RS, 1'RS, 3RS, 3'RS, 5RS, 5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] ((+/-)-6) derived from 2,2'-methylenedifuran has been resolved kinetically with Candida cylindracea lipase-catalysed transesterification giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] (-)-6 (30% yield, 98% ee) and 1,1'-methylenedi[(1S, 1'S, 3S, 3'S, 5S, 5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate (+)-8, (40% yield, 98% ee). These compounds have been converted into 1,1'-methylenedi[(4S, 4'S, 6S, 6'S)- and (4R, 4'R, 6R, 6'R)-cyclohept-1-en-4,6-diyl] derivatives. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00475-4
• 作为产物：
  描述：

  (+/-)-1,1'-Methylenedi[(1RS,1'RS,5SR,5'SR)-3-oxo-8-oxabicyclo[3.2.1]oct-6-ene] 在 potassium tri-sec-butyl-borohydride 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(-)-1,1'-methylenedi[(1R,1'R,3R,3'R,5R,5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol]
  参考文献：
  名称：

  Synthesis of 1,1′-methylenedi[(1 R ,1′ R ,3 R ,3′ R ,5 R ,5′ R )-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketides

  摘要：

  Racemic 1,1'-methylene[(1RS, 1'RS, 3RS, 3'RS, 5RS, 5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] ((+/-)-6) derived from 2,2'-methylenedifuran has been resolved kinetically with Candida cylindracea lipase-catalysed transesterification giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] (-)-6 (30% yield, 98% ee) and 1,1'-methylenedi[(1S, 1'S, 3S, 3'S, 5S, 5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate (+)-8, (40% yield, 98% ee). These compounds have been converted into 1,1'-methylenedi[(4S, 4'S, 6S, 6'S)- and (4R, 4'R, 6R, 6'R)-cyclohept-1-en-4,6-diyl] derivatives. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00475-4

文献信息

• Synthesis of 1,1′-methylenedi[(1 R ,1′ R ,3 R ,3′ R ,5 R ,5′ R )-8-oxabicyclo[3.2.1]oct-6-en-3-ol] and derivatives: precursors of long-chain polyketides
  作者：Aurelio G. Csákÿ、Pierre Vogel

  DOI：10.1016/s0957-4166(00)00475-4

  日期：2000.12

  Racemic 1,1'-methylene[(1RS, 1'RS, 3RS, 3'RS, 5RS, 5'RS)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] ((+/-)-6) derived from 2,2'-methylenedifuran has been resolved kinetically with Candida cylindracea lipase-catalysed transesterification giving 1,1'-methylenedi[(1R, 1'R, 3R, 3'R, 5R, 5'R)-8-oxabicyclo[3.2.1]oct-6-en-3-ol] (-)-6 (30% yield, 98% ee) and 1,1'-methylenedi[(1S, 1'S, 3S, 3'S, 5S, 5'S)-8-oxabicyclo[3.2.1]oct-6-en-3-yl] diacetate (+)-8, (40% yield, 98% ee). These compounds have been converted into 1,1'-methylenedi[(4S, 4'S, 6S, 6'S)- and (4R, 4'R, 6R, 6'R)-cyclohept-1-en-4,6-diyl] derivatives. (C) 2001 Published by Elsevier Science Ltd.