(E)-(R)-2-((5S,7S)-7-Isopropyl-5,9-dihydro-6,8-dioxa-benzocyclohepten-5-yl)-2-methyl-pent-3-enoic acid methyl ester | 887130-09-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-(R)-2-((5S,7S)-7-Isopropyl-5,9-dihydro-6,8-dioxa-benzocyclohepten-5-yl)-2-methyl-pent-3-enoic acid methyl ester
• 英文别名: methyl (E,2R)-2-methyl-2-[(3S,5S)-3-propan-2-yl-1,5-dihydro-2,4-benzodioxepin-5-yl]pent-3-enoate
• CAS: 887130-09-8
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: YNEUXMNDKLBYNW-QBGQDRDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(R)-2-((5S,7S)-7-Isopropyl-5,9-dihydro-6,8-dioxa-benzocyclohepten-5-yl)-2-methyl-pent-3-enoic acid methyl ester 在 四氯化锡 、 silver carbonate 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (4S,5R)-5-hydroxy-2,4,6-trimethylhept-2-enoic acid methyl ester
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f
• 作为产物：
  描述：

  (E)-(R)-2-{(S)-Acetoxy-[2-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-methyl}-2-methyl-pent-3-enoic acid methyl ester 在 tin(II) trifluoromethanesulfonate 、 肼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (E)-(R)-2-((5S,7S)-7-Isopropyl-5,9-dihydro-6,8-dioxa-benzocyclohepten-5-yl)-2-methyl-pent-3-enoic acid methyl ester
  参考文献：
  名称：

  New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements

  摘要：

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.

  DOI：

  10.1021/ja061082f

文献信息

• New Chiral Synthons for Efficient Introduction of Bispropionates via Stereospecific Oxonia−Cope Rearrangements
  作者：Yi-Hung Chen、Frank E. McDonald

  DOI：10.1021/ja061082f

  日期：2006.4.1

  Compounds 1 and 2 are novel synthons for bispropionate synthesis, undergoing stereospecific Lewis acid-catalyzed transfer of the bispropionate unit with a variety of aldehydes, including alpha-chiral aldehydes. Thus 1 leads to the E-alkene bispropionate 3 with anti-stereochemistry, whereas diastereomer 2 gives the Z-alkene product 4, under mild conditions and with complete stereospecificity. The efficacy of this methodology is demonstrated in a short synthesis of invictolide beginning with 2 and (R)-2-methylpentanal.