trans-β-methyl-γ-isopropyl-γ-butyrolactone | 85710-97-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: trans-β-methyl-γ-isopropyl-γ-butyrolactone
• 英文别名: trans-4-Methyl-5-(1-methylethyl)-4,5-dihydrofuran-2(3H)-on；(4S*,5R*)-4,5-dihydro-5-isopropyl-4-methyl-2(3H)-furanone；trans-β-methyl-γ-isopropyl-γ-lactone；(4RS,5SR)-4-Methyl-5-propan-2'-yldihydrofuran-2(3H)-one；(4R,5S)-4-methyl-5-propan-2-yloxolan-2-one
• CAS: 85710-97-0
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: VZCKPIXXIZDDDT-SVRRBLITSA-N

物化性质

• 沸点：
  90 °C(Press: 3 Torr)
• 密度：
  0.958±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-bromo-2-ethoxy-4-isopropyl-3-oxa-5-hexene 在 jones reagent 、 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 trans-β-methyl-γ-isopropyl-γ-butyrolactone
  参考文献：
  名称：

  Free-radical cyclization of bromo acetals. Use in the construction of bicyclic acetals and lactones

  摘要：

  DOI：

  10.1021/ja00349a082

文献信息

• Efficient Remote Axial-to-Central Chirality Transfer in Enantioselective SmI₂-Mediated Reductive Coupling of Aldehydes with Crotonates of Atropisomeric 1-Naphthamides
  作者：Yan Zhang、Yongqiang Wang、Wei-Min Dai

  DOI：10.1021/jo0526486

  日期：2006.3.1

  different 2-substituted 8-methoxy-1-naphthamides. The enantiomers of atropisomeric 8-methoxy-1-naphthamides were prepared through a chemical resolution process, and their absolute stereochemistry was determined by X-ray crystal structural analysis. It was found that the linkage between crotonate and the C2 position of 8-methoxy-1-naphthamides remarkably influenced the efficiency of remote chirality transfer

  在SmI 2介导的醛与具有不同的2-取代的8-甲氧基-1-萘酰胺的巴豆酸酯的还原偶联中，已经研究了通过远程酰胺构象控制对映选择性的方法。通过化学拆分方法制备对映异构体8-对甲氧基-1-萘酰胺的对映异构体，并通过X射线晶体结构分析确定其绝对立体化学。发现巴豆酸酯和8-甲氧基-1-萘酰胺的C2位之间的键合显着影响源自酰胺构象的远程手性转移的效率。在所检查的四种巴豆酸酯中，一种由2-羟基-8-甲氧基-1-萘酰胺衍生的戊烯酸酯与戊醛反应，以使顺式的ee最高，> 99％-γ-丁内酯，合并产率为90％，顺/反比为90:10。我们开发了一种在温和条件下通过C8氧将手性巴豆酸酯连接到Rink酰胺树脂上的新程序，并在固相反应中获得了相同水平的极远的轴向向中心手性转移。
• Stereoselective synthesis of substituted γ-butyrolactones from γ-hydroxy-α,β-unsaturated phenyl sulfones
  作者：Javier Rojo、Mercedes García、Juan C Carretero

  DOI：10.1016/s0040-4020(01)80181-2

  日期：1993.1

  α-(phenylsulfonyl)-α,β-unsaturated esters 3 or α-(phenylsulfonyl)butenolides 4 is described. This method is based on the conjugate addition of organoaluminum reagents (Me3Al, Et3Al and Et2AlCN) to substrates 3 and 4. Whereas the conjugate addition to Michael acceptors 3 occurs with complete syn-selectivity, the conjugate addition to butenolides 4 is usually anti-selective. This methodology has been applied

  描述了从容易获得的α-（苯磺酰基）-α，β-不饱和酯3或α-（苯磺酰基）丁烯化物4开始制备顺式和反式双取代（和三取代）γ-内酯的立体选择路线。该方法基于将有机铝试剂（Me 3 Al，Et 3 Al和Et 2 AlCN）共轭添加到基质3和4上。尽管共轭加成到迈克尔受体3时具有完全的同选择性，而共轭加成成丁烯脂类4通常是反选择的。该方法已经应用于（-）-顺式白兰地内酯的立体选择性和对映选择性合成。
• On the use of E-1-methoxymethoxybut-2-enyl(tri-n-butyl)stannane as a threo-selective, homo-enolate equivalent
  作者：Andrew J. Pratt、Eric J. Thomas

  DOI：10.1039/c39820001115

  日期：——

  (E)-1-Methoxymethoxybut-2-enyl(tri-n-butyl)stannane, readily available by addition of tri-n-butylstannyllithium to crotonaldehyde, and protection of the alcohol so formed using chloromethyl methyl ether, reacts on heating with aromatic and aliphatic aldehydes to give threo-4,5-disubstituted butyrolactones.

  （E）-1-甲氧基甲氧基丁-2-烯基（三正丁基）锡烷，可通过将三正丁基锡锂加到巴豆醛中而容易获得，并用氯甲基甲基醚保护如此形成的醇，在加热下与芳族化合物反应和脂族醛得到苏--4，5-二取代丁内酯。
• A novel stereoselective synthesis of substituted γ-butyrolactones
  作者：Juan C. Carretero、Javier Rojo

  DOI：10.1016/s0040-4039(00)60201-0

  日期：1992.11

  A new stereoselective synthetic route for the preparation of cis and trans disubstituted (and trisubstituted) γ-lactones starting from the readily available α-phenylsulfonyl-α,β-unsaturated esters 3 or α-phenylsulfonylbutenolides 4 is described. This method is based on the conjugate addition of Me3Al to compounds 3 and 4, which occurs with high, though opposite, facial selectivity.

  描述了从容易获得的α-苯基磺酰基-α，β-不饱和酯3或α-苯基磺酰基丁烯化物4开始制备顺式和反式双取代（和三取代）γ-内酯的新的立体选择性合成路线。该方法基于将Me 3 Al共轭添加到化合物3和4中，尽管面部选择性高，但选择性相反。
• Dichotomous regiochemistry of aldehyde and ketone in the reaction with dithio-substituted crotyllithium
  作者：Jim Min Fang、Bor Cherng Hong、Li Fan Liao

  DOI：10.1021/jo00381a026

  日期：1987.3