(S)-(-)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone | 124988-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-(-)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone
• 英文别名: (S)-(-)-4-(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one；(S)-4-<<4-(benzyloxy)-3-methoxyphenyl>methyl>dihydro-2(3H)-furanone；(4S)-4-[(3-methoxy-4-phenylmethoxyphenyl)methyl]oxolan-2-one
• CAS: 124988-58-5
• 化学式: C₁₉H₂₀O₄
• 分子量: 312.365
• InChiKey: FKRJBUYHQOXRCE-INIZCTEOSA-N

物化性质

• 熔点：
  73-74.5 °C
• 沸点：
  493.6±30.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 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：

  (S)-(-)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone 在 12-冠醚-4 氧气 、 lithium hexamethyldisilazane 作用下， 以 苯 为溶剂， 反应 3.0h， 生成 (+)-O-dibenzylnortrachelogenine
  参考文献：
  名称：

  （-）-trachelogenin，（-）-nortrachelogenin和（+）-wikstromol的总合成

  摘要：

  通过相应的α，β-二苄基-γ-丁内酯（合成来源的木脂素）的α-羟基化获得标题化合物，并将其与（±）-甲基trachelogenin 9相关联，后者的相对结构通过X射线结晶成像法确定。因此，（-）-Trachelogenin 1和（-）-nortrachelogenin 12具有（8S，8'S）绝对构型，而（+）-nortrachelogenin 20（或wikstromol）具有（8R，8'R）绝对构型。

  DOI：

  10.1016/s0040-4039(00)99653-9
• 作为产物：
  描述：

  3-(4-羟基-3-甲氧基苯基)丙酸 在 2,6-二甲基吡啶 、 sodium periodate 、 四氧化锇 、 锂硼氢 、 正丁基锂 、 水 、 双(三甲基硅烷基)氨基钾 、 potassium carbonate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 正己烷 、 水 、 丙酮 、 苯 为溶剂， 反应 7.17h， 生成 (S)-(-)-3-(4-benzyloxy-3-methoxybenzyl)-γ-butyrolactone
  参考文献：
  名称：

  手性β-苄基-γ-丁内酯的获取及其在对映体纯（+）-异豆香脂醇，（-）-异豆香脂醇和（-）-肠内酯的合成中的应用

  摘要：

  通过高立体选择性会聚合成法合成了癸二异胡香脂树脂醇对映体和对映体纯（-）-内酯。Evans非对映选择性烷基化，然后是新形成的旋光性β-苄基-γ-丁内酯的底物诱导的非对映选择性α-烷基化，形成了目标骨架的β-β'键。癸二异戊二烯树脂醇的（S，S）-和（R，R）-对映异构体和（-）-对内酯的总产率分别为12-14％（11步）和20％（7步）。 全合成-天然产物-内酯-不对称-非对映选择性烷基化

  DOI：

  10.1055/s-0030-1259982

文献信息

• Total Synthesis of (<i>S</i>)-(+)-Imperanene. Effective Use of Regio- and Enantioselective Intramolecular Carbon−Hydrogen Insertion Reactions Catalyzed by Chiral Dirhodium(II) Carboxamidates
  作者：Michael P. Doyle、Wenhao Hu、Marcela V. Valenzuela

  DOI：10.1021/jo016220s

  日期：2002.5.1

  completed in 12 steps from a commercially available cinnamic acid. The key step is highly enantioselective carbon-hydrogen insertion from a diazoacetate using a chiral dirhodium(II) carboxamidate catalyst. An elimination process essential to the construction has been optimized to avoid intramolecular Friedel-Crafts alkylation.

  中药中的天然产物（S）-（+）-imperanene的总合成已由市售肉桂酸分12步完成。关键步骤是使用手性氨基羧酸二铵（II）催化剂从重氮乙酸盐中插入高度对映选择性的碳氢。优化了该结构必不可少的消除工艺，以避免分子内Friedel-Crafts烷基化。
• Asymmetric synthesis of (R)- and (S)-4-(substituted benzyl)dihydrofuran-2(3H)-ones: an application of the ruthenium-binap complex-catalysed asymmetric hydrogenation of alkylidenesuccinic acids
  作者：Liming Shao、Shiro Miyata、Hitoshi Muramatsu、Hiroyuki Kawano、Youichi Ishii、Masahiko Saburi、Yasuzo Uchida

  DOI：10.1039/p19900001441

  日期：——

  A concise synthesis of (S)- or (R)-4-(substituted benzyl)dihydrofuran-2(3H)-ones (1) with high enantiomeric purity is presented. (S)- or (R)-(Substituted benzyl)succinic acids (6) 97% enantiomeric excess) were first prepared by Ru2Cl4[(R)- or (S)-binap)]2(NEt3) catalysed asymmetric hydrogenation of (substituted benzylidene)succinic acids. The diacids (6) were converted into (R)- or (S)-2-(substituted

  提出了具有高对映体纯度的（S）-或（R）-4-（取代的苄基）二氢呋喃-2（3 H）-ones（1）的简明合成方法。首先通过Ru 2 Cl 4 [（R）-或（S）-binap）] 2（NEt 3）催化制备（S）-或（R）-（取代的苄基）琥珀酸（6），对映体过量97％）。 （取代的亚苄基）琥珀酸的不对称氢化。将二酸（6）转化为（R）-或（S）-2-（取代的苄基）丁烷-1,4-二醇（9）和随后的RuH 2（PPh 3）4催化的（9）脱氢内酯化反应，得到内酯（1），其手性构型完全保留中心。
• Antioxidant Activity of Butane Type Lignans, Secoisolariciresinol, Dihydroguaiaretic Acid, and 7,7′-Oxodihydroguaiaretic Acid
  作者：Satoshi YAMAUCHI、Toshiya MASUDA、Takuya SUGAHARA、Yuya KAWAGUCHI、Maya OHUCHI、Tatsushi SOMEYA、Jun AKIYAMA、Shiori TOMINAGA、Manami YAMAWAKI、Taro KISHIDA、Koichi AKIYAMA、Masafumi MARUYAMA

  DOI：10.1271/bbb.80461

  日期：2008.11.23

  The antioxidant activity of butane-type lignans was evaluated. Secoisolariciresinol (SECO) and dihydroguaiaretic acid (DGA) showed higher radical scavenging activity than that of 7,7′-dioxodihydroguaiaretic acid (ODGA). SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity.

  对丁烷类木酚素的抗氧化活性进行了评估。与 7,7′-二氧二氢愈创木脂酸（ODGA）相比，仲异月桂醇（SECO）和二氢愈创木脂酸（DGA）具有更高的自由基清除活性。SECO 和 DGA 可抑制不饱和脂肪酸的氧化。DGA 的两种对映体也是脂氧合酶抑制剂，但 SECO 的两种对映体都不能抑制脂氧合酶的活性。
• Intramolecular Regioselective Insertion into Unactivated Prochiral Carbon−Hydrogen Bonds with Diazoacetates of Primary Alcohols Catalyzed by Chiral Dirhodium(II) Carboxamidates. Highly Enantioselective Total Synthesis of Natural Lignan Lactones
  作者：Jeffrey W. Bode、Michael P. Doyle、Marina N. Protopopova、Qi-Lin Zhou

  DOI：10.1021/jo961607u

  日期：1996.1.1

  Intramolecular insertion into unactivated prochiral C-H bonds of 3-aryl-1-propyl diazoacetates catalyzed by dirhodium(II) tetrakis[methyl 1-(3-phenyl propanoyl)imidazolidin-2-one-4(R or S)-carboxylate], Rh-2(4R-MPPIM)(4) or Rh-2(4S-MPPIM)(4), occurs in 91-96% ee and with virtually complete regiocontrol for the formation of beta-benzyl-gamma-butyrolactones. This methodology has been applied to the total synthesis of dibenzylbutyrolactone lignans (-)- and (+)-enterolactone, (-)- and (+)-hinokinin, and (+)-arctigenin from substituted cinnamic acids in 19-27% overall yields. Aryltetralin lignan (+)-isodeoxypodophyllotoxin was prepared from the reactant 3,4-(methylenedioxy)cinnamic acid in 36% yield overall, and the lactone precursor to (+)-isolauricerisinol was formed in 96.5% ee and 23% yield overall. Applications of the chiral Rh-2(MPPIM)4 catalysts to fully aliphatic systems resulting in the formation of beta-substituted-gamma-butyrolactones with high regiocontrol and with 93-96% ee have demonstrated the generality of this methodology. A model that provides accurate predictions of beta-substituted-gamma-butyrolactone absolute configurations in these asymmetric metal carbene transformations is described.
• Lignanes. 16. Premières synthèses totales du (+)-wikstromol, de la (−)-trachélogénine, de la (−)-nortrachélogénine et des lignoïdes apparentés
  作者：Melle Kenza Khamlach、Robert Dhal、Eric Brown

  DOI：10.1016/s0040-4020(01)89041-4

  日期：——

  Racemic and optically active alpha,beta-dibenzyl-gamma-butyrolactones (of synthetic origin) were hydroxylated in the alpha position with respect to the carbonyl group, using oxygen in the presence of LHDS. This led to (-)-trachelogenin 1, (-)-nortrachelogenin 2 and (+)-wikstromol 3, whose interesting pharmacological properties were recently described. These natural lignans were correlated to (+/-)-methyltrachelogenin 12 whose relative structure was definitely established by X-ray cristallography.