(3E)-3-(4,8-dimethylnon-3,7-dienyl)but-2-en-4-olide | 61315-76-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3E)-3-(4,8-dimethylnon-3,7-dienyl)but-2-en-4-olide
• 英文别名: 3-[(3E)-4,8-dimethylnona-3,7-dienyl]-2H-furan-5-one
• CAS: 61315-76-2
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: FNHHDLJGCKAXKZ-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3E)-3-(4,8-dimethylnon-3,7-dienyl)but-2-en-4-olide 在 potassium osmate(VI) 、 甲基磺酰胺 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 以72%的产率得到(3E)-3-(7,8-dihydroxy-4,8-dimehtylnon-3-enyl)but-2-en-4-olide
  参考文献：
  名称：

  Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P

  摘要：

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.11.019
• 作为产物：
  描述：

  香叶基丙酮 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 5.5h， 生成 (3E)-3-(4,8-dimethylnon-3,7-dienyl)but-2-en-4-olide
  参考文献：
  名称：

  Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P

  摘要：

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2015.11.019

文献信息

• A new synthesis of Δ2-butenolides via stereoselective formation of α,β-ethylenic esters.
  作者：M. Larcheveque、Ch. Legueut、A. Debal、J.Y. Lallemand

  DOI：10.1016/s0040-4039(01)90386-7

  日期：1981.1

  A new synthesis of Δ2-butenolides is described which involves stereoselective condensation of an α-silyl ester anion with an α-ketoacetal.

  Δ的新合成2 -butenolides被描述，包括用α-ketoacetalα-甲硅烷基酯阴离子的立体选择性缩合。
• A palladium-catalyzed stereospecific substitution reaction of homoallylzincs with .beta.-bromo-substituted .alpha.,.beta.-unsaturated carbonyl derivatives. A highly selective synthesis of mokupalide
  作者：Makoto Kobayashi、Eiichi Negishi

  DOI：10.1021/jo01313a048

  日期：1980.12
• Biomimetic synthesis of (.+-.)-pallescensin 1
  作者：Marcus A. Tius、Katherine S. Takaki

  DOI：10.1021/jo00137a027

  日期：1982.7
• Preparation of (S)-γ-cyclogeraniol by lipase-catalyzed transesterification and synthesis of (+)-trixagol and (+)-luffarin-P
  作者：Mikio Fujii、Yosuke Morimoto、Machiko Ono、Hiroyuki Akita

  DOI：10.1016/j.molcatb.2015.11.019

  日期：2016.1

  Lipase-catalyzed kinetic resolution of gamma-cyclogeraniol by Candida antarctica lipase B yielded 23% of enantiomerically pure (S)-gamma-cyclogeraniol. (+)-trixagol and (+)-luffarin-P were synthesized from the obtained (S)-gamma-cyclogeraniol, and the absolute configuration of natural (+)-luffarin-P was determined to have an S configuration by our first synthesis of (S)-luffarin-P for the first time. (C) 2015 Elsevier B.V. All rights reserved.