(4'S,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one | 162333-93-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4'S,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one
• 英文别名: (3E)-3-[[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]oxolan-2-one
• CAS: 162333-93-9
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: XGUUHNVDUCPMCH-IVGLGHLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  (4'S,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one 在 镍 氢气 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 为溶剂， 45.0~50.0 ℃ 、5.07 MPa 条件下， 反应 35.0h， 生成 (3S,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(2-hydroxyethyl)-2-pyrrolidinone
  参考文献：
  名称：

  Stereoselective synthesis of 3-(ω-hydroxyalkyl)-2-pyrrolidinones from α-alkylidenelactones and nitromethane

  摘要：

  Enantiopure 3-(omega-hydroxyalkyl)-2-pyrrolidinones 7 and 9 were synthesised by Michael-addition of nitromethane to chiral alpha-alkylidenelactones 1 followed by reduction of the resulting 3-(beta-nitroalkyl)-lactones and ring transformation of the intermediate 3-(beta-aminoalkyl)-lactones. In an analogous manner the naturally occurring costuslactone 10 was transformed into the butyrolactam 12. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00346-8
• 作为产物：
  描述：

  γ-丁内酯 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 在 甲基磺酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 lithium diisopropyl amide 作用下， 生成 (4'S,Z)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one 、 (4'S,E)-3-(2',2'-dimethyl-1',3'-dioxolan-4'-ylmethylene)tetrahydrofuran-2-one
  参考文献：
  名称：

  Stereoselective radical additions of γ-oxy-α,β-unsaturated ester derivatives; 1,2-asymmetric induction in acyclic and cyclisation systems

  摘要：

  Examination was made of 1,2-asymmetric induction in the addition of alkyl radicals to gamma-oxy-alpha,beta-unsaturated ester derivatives 1 and 2 prepared from ethyl lactate and (R)-2,3-0-isopropylideneglyceraldehyde 3, respectively. The addition reactions of hexyl, cyclohexyl and 3-phenylpropyl radicals to (Z)-2 derived from aldehyde 3 gave beta-addition products with syn-stereoselectivity (syn:anti = 8.6:1-syn only). The reactions of (E)-2 were non-stereoselective. Based on allylic strain, a transition-state model for the syn-stereoselectivity is proposed. 1,2-Asymmetric induction was carried out in radical cyclisation to synthesize optically active cyclohexane derivatives.

  DOI：

  10.1039/p19950000271

文献信息

• Synthesis of optically active hydroxyalkylbenzothiazepinones by ring transformation of 2-alkylidenelactons with<i>o</i>-aminothiophenol
  作者：Andreas Otto、Jürgen Liebscher

  DOI：10.1002/jhet.5570370436

  日期：2000.7

  A stereoselective synthesis of new optically active 3-(hydroxyalkyl)-2,3-dihydro-1,5-benzothiazepin-4-ones 4 and 7 was achieved by Michael-like addition of o-aminothiophenol to chiral α-alkylidenelactons 1 and 5 followed by ring chain transformation of the resulting adducts 3 and 6.

  立体选择性合成新的旋光的3-（羟烷基）-2,3-二氢-1,5-苯并噻唑啉-4-酮4和7是通过将迈克尔-邻氨基硫酚类似迈克尔地添加到手性α-烷基亚内酯1和5上而实现的然后对所得的加合物3和6进行环链转化。
• Otto, Andreas; Liebscher, Juergen, Synthesis, 2003, # 8, p. 1209 - 1214
  作者：Otto, Andreas、Liebscher, Juergen

  DOI：——

  日期：——
• Optically Active α-Spirocyclopropyllactones and 3-Aminopyrrolidones via Stereoselective Diazoalkane Cycloaddition at α-Alkylidenelactones
  作者：Andreas Otto

  DOI：10.1055/s-1999-6065

  日期：1999.6