(7’R, 8’R)-4,7’-epoxy-3’,5-di-O-methyl-3’,4’,5,9,9’-pentahydroxy-3,8’-bilignan | 133318-48-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (7’R, 8’R)-4,7’-epoxy-3’,5-di-O-methyl-3’,4’,5,9,9’-pentahydroxy-3,8’-bilignan
• 英文别名: (+)-(7S,8R)-dihydrodehydrodiconiferyl alcohol；(7'R, 8'R)-dihydrodehydrodiconiferyl alcohol；vladinol F；4-[(2R,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2-methoxyphenol
• CAS: 133318-48-6
• 化学式: C₂₀H₂₄O₆
• 分子量: 360.407
• InChiKey: SBLZVJIHPWRSQQ-KXBFYZLASA-N

物化性质

• 沸点：
  540.9±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (7’R, 8’R)-4,7’-epoxy-3’,5-di-O-methyl-3’,4’,5,9,9’-pentahydroxy-3,8’-bilignan 在 吡啶 作用下， 生成 Acetic acid (2R,3R)-2-(4-acetoxy-3-methoxy-phenyl)-5-(3-acetoxy-propyl)-7-methoxy-2,3-dihydro-benzofuran-3-ylmethyl ester
  参考文献：
  名称：

  来自冷杉针叶的二萜醇苷

  摘要：

  摘要 (2R,3R)-2 3-Dihydro-2-(4'-羟基-3'-甲氧基苯基)-3-(羟甲基)-7-甲氧基-5-苯并呋喃丙醇 4'-O-β-d-吡喃葡萄糖苷[二氢脱氢二松果醇葡萄糖苷], (2R,3R)-2 3-dihydro-7-hydroxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranpropanol 4'-O-β- d-吡喃葡萄糖苷和 4'-O-α-l-吡喃鼠李糖苷，1-(4'-羟基-3'-甲氧基苯基)-2-[2"-羟基-4"-(3-羟丙基)苯氧基]-1， 3-丙二醇 1-O-β-d-吡喃葡萄糖苷和 4'-O-β-d-吡喃木糖苷，2,3-双[(4'-羟基-3'-甲氧基苯基)-甲基]-1,4-丁二醇1-O-β-d-吡喃葡萄糖苷 [(-)-seco-isolariciresinol glucoside]

  DOI：

  10.1016/0031-9422(81)84046-0
• 作为产物：
  描述：

  2,3-dihydro-2-(4'-hydroxy-3'-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-5-benzofuranopropanol 4'-O-β-glucopyranoside 以 水 为溶剂， 以29 mg的产率得到(7’R, 8’R)-4,7’-epoxy-3’,5-di-O-methyl-3’,4’,5,9,9’-pentahydroxy-3,8’-bilignan
  参考文献：
  名称：

  来自冷杉针叶的二萜醇苷

  摘要：

  摘要 (2R,3R)-2 3-Dihydro-2-(4'-羟基-3'-甲氧基苯基)-3-(羟甲基)-7-甲氧基-5-苯并呋喃丙醇 4'-O-β-d-吡喃葡萄糖苷[二氢脱氢二松果醇葡萄糖苷], (2R,3R)-2 3-dihydro-7-hydroxy-2-(4'-hydroxy-3'-methoxyphenyl)-3-(hydroxymethyl)-5-benzofuranpropanol 4'-O-β- d-吡喃葡萄糖苷和 4'-O-α-l-吡喃鼠李糖苷，1-(4'-羟基-3'-甲氧基苯基)-2-[2"-羟基-4"-(3-羟丙基)苯氧基]-1， 3-丙二醇 1-O-β-d-吡喃葡萄糖苷和 4'-O-β-d-吡喃木糖苷，2,3-双[(4'-羟基-3'-甲氧基苯基)-甲基]-1,4-丁二醇1-O-β-d-吡喃葡萄糖苷 [(-)-seco-isolariciresinol glucoside]

  DOI：

  10.1016/0031-9422(81)84046-0

文献信息

• Benzo[<i>f</i>][1,2]oxasilepines in the Synthesis of Dihydro[<i>b</i>]benzofuran Neolignans
  作者：Ignacio Rodríguez-García、Sergio García-Muñoz、Leticia Jiménez-González、Míriam Álvarez-Corral、Manuel Muñoz-Dorado

  DOI：10.1055/s-2005-921913

  日期：——

  A short synthesis of neolignans with a dihydrobenzo[b]furan skeleton is described. The strategy is based on a ring-closing metathesis to produce benzo[f][1,2]oxasilepines which are condensed with aromatic aldehydes in a modified Sakurai-Hosomi reaction. Natural dihydrodehydrodiconiferyl alcohol (1) and 3-0-demethyldihydrodehydrodiconiferyl alcohol (2) have been prepared in this way.

  描述了具有二氢苯并 [b] 呋喃骨架的新木脂素的简短合成。该策略基于闭环复分解，以生产苯并[f][1,2] oxasilepines，在改进的Sakurai-Hosomi 反应中与芳香醛缩合。用这种方法制备了天然二氢脱氢二松香醇（1）和3-0-脱甲基二氢脱氢二松香醇（2）。
• Synthesis of dihydrodehydrodiconiferyl alcohol: the revised structure of lawsonicin
  作者：Junxiu Meng、Tao Jiang、Huma Aslam Bhatti、Bina S. Siddiqui、Sally Dixon、Jeremy D. Kilburn

  DOI：10.1039/b918179b

  日期：——

  Structural revision of lawsonicin, a natural product of Lawsonia alba, is reported based upon comparison of its spectral data with that of the naturally occurring dihydrobenzo[b]furan neolignan (rac)-trans-dihydrodehydrodiconiferyl alcohol, which is found to be identical. A concise synthesis of dihydrodehydrodiconiferyl alcohol, via Rh2[S-DOSP]4-catalysed intramolecular C–H insertion, is described.

  根据与天然存在的二氢苯并[b]呋喃新木质素（rac）-反式-二氢去氢二苯醇的光谱数据比较，报道了天芥菜（Lawsonia alba）天然产物lawsonicin的结构修订。还描述了通过Rh2[S-DOSP]4催化的分子内C-H插入反应合成二氢去氢二苯醇的简洁合成方法。
• Six new dihydrobenzofuran lignans from the branches and leaves of Illicium wardii and their cytotoxic activities
  作者：Feng-mei Ye、Yang-guo Xie、Jie Ren、Ji Ye、Yi-gong Guo、Shi-Kai Yan、Hui-Zi Jin、Wei-Dong Zhang

  DOI：10.1016/j.phytol.2016.07.010

  日期：2016.9

  Six new dihydrobenzofuran lignans, named illiciumlignans A⿿F (compounds 1⿿6), along with 15 known compounds (7⿿21) were isolated from the branches and leaves of Illicium wardii. The structures of 1⿿6 were determined using a combination of 1D and 2D NMR, HR-ESI⿿-MS, and CD spectroscopic data. Illiciumlignan D (4) is the first reported dihydrobenzofuran lignan arabinofuranoside that is derivatized with

  六个新的二氢苯并呋喃木脂素，命名为illiciumlignansA⿿F（化合物1⿿6）中，用15种已知化合物（沿7 ⿿ 21）获自的枝叶分离八角wardii。的结构1⿿6使用一维和二维NMR，HR-ESI⿿-MS，和CD光谱数据的组合进行了测定。Illiciumlignan D（4）是第一个报道的二氢苯并呋喃木脂素阿拉伯呋喃糖苷，它被C-9上的阿拉伯呋喃糖部分衍生。化合物1 ⿿ 21针对四种人类肿瘤细胞株的细胞毒活性进行评价。化合物8，12和20具有抗人类癌细胞系（A549，SKOV3，HepG2和HCT116）的显着活性，IC 50值为2.7至14.9μM。