(3R)-(+)-3-(4-Hydroxy-3-methoxybenzyl)butan-4-olide | 111266-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (3R)-(+)-3-(4-Hydroxy-3-methoxybenzyl)butan-4-olide
• 英文别名: (R)-(+)-3-(4-hydroxy-3-methoxybenzyl)-γ-butyrolactone；(R)-4-<(4-hydroxy-3-methoxyphenyl)methyl>dihydro-2(3H)-furanone；(R)-(+)-β-vanillyl-γ-lactone；(4R)-4-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
• CAS: 111266-00-3
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: VKCHEYIDBYCQPR-SECBINFHSA-N

物化性质

• 熔点：
  119.5-121.5 °C
• 沸点：
  427.6±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.51
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (3R)-(+)-3-(4-Hydroxy-3-methoxybenzyl)butan-4-olide 在 palladium on activated charcoal 氢气 、 potassium carbonate 、 potassium iodide 、 lithium diisopropyl amide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， -80.0 ℃ 、300.0 kPa 条件下， 反应 34.0h， 生成 (-)-thujaplicatin methyl ether
  参考文献：
  名称：

  The Syntheses of (R)-(+)-b-Vanillyl-g-butyrolactone and of Chiral Lignans Therefrom

  摘要：

  DOI：

  10.3987/r-1987-05-1169
• 作为产物：
  描述：

  (R)-(+)-methyl α-vanillylhemisuccinate 在 calcium borohydride 作用下， 生成 (3R)-(+)-3-(4-Hydroxy-3-methoxybenzyl)butan-4-olide
  参考文献：
  名称：

  First total synthesis of (−)-α-conidendrin

  摘要：

  DOI：

  10.1016/s0040-4039(00)99363-8

文献信息

• Lignanes. 15. Première Synthèse Totale de la (−)-α-Conidendrine Naturelle
  作者：Partrick Boissin、Robert Dhal、Eric Brown

  DOI：10.1016/s0040-4020(01)88129-1

  日期：——

  (−)-α-Conidendrin 1 was synthesized according to a general reactionscheme that could be applied to other retrolignans as well. Thus, treatment of the optically active β-benzyl-γ-butyrolactone (R)-(+)- 4 with NBS, followed with benzyl alcohol, selectively introduced a benzyloxy group in the benzylic position and afforded the mixture of epimers 7. α-Alkylation of the lithium enolate of the corresponding

  （-）-α-伴生蛋白1是根据一般反应化学合成的，该化学反应也可应用于其他逆向木脂素。因此，用NBS处理光学活性β-苄基-γ-丁内酯（R）-（+）- 4，然后用苯甲醇，在苄基位置选择性引入苄氧基，得到差向异构体7的混合物。相应的甲硅烷基醚10的烯醇锂的α-烷基化与O-苄基香草基溴化物11一起，给出了反式二取代的内酯13（2个差向异构体）。催化氢解的钯（Pd-C）13选择性地分裂芳苄醚键，并给出了化合物14。后者，使用苄氧基作为离去基团，被诱导与BF的分子内弗里德尔-克拉夫茨环化3 -Et 2（ - ） - α-conidendrin O和得到1在36％的总选自甲基α-vanillylhemis uccinate（收率ř）-（+）- 17。
• Discovery of stereospecific cytotoxicity of (8R,8′R)-trans-arctigenin against insect cells and structure-activity relationship on aromatic ring
  作者：Satoshi Yamauchi、Asuka Nishimoto、Hisashi Nishiwaki、Kosuke Nishi、Takuya Sugahara

  DOI：10.1016/j.bmcl.2020.127191

  日期：2020.7

  One of the arctigenin stereoisomers, (8R,8'R)-trans-form 1, showed stereospecific cytotoxicity against insect cells, Sf9 and NIAS-AeAl-2 cells. By the comparison with other stereoisomers, the most importance of the 8'R stereochemistry for the higher activities was clarified. On the other hand, the wider range of activity level among stereoisomers against cancer cells, HL-60, was not observed. The structure-activity relationship research using derivatives bearing (8R,8'R)-trans-form was performed to show the same level of activities of 3-iodo, 4-iodo, and 3,4-methylenedioxy derivatives 28, 29, and 36 as (8R,8'R)-trans-arctigenin 1. In the examination of thiono derivatives, 4-iodo thiono and 3,4-methylenedioxy thiono derivatives 66, 67 showed similar level of activities to that of (8R,8'R)-trans-arctigenin 1. The expression of ribosomal 28S rRNA gene of Sf9 cells was increased by (8R,8'R)-trans-arctigenin 1, whereas a degradation of DNA was not observed.
• 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.
• BOISSIN, PATRICK;DHAL, ROBERT;BROWN, ERIC, TETRAHEDRON LETT., 30,(1989) N3, C. 4371-4374
  作者：BOISSIN, PATRICK、DHAL, ROBERT、BROWN, ERIC

  DOI：——

  日期：——