(+)-利卡灵 | 42016-15-9

• 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
• 中文名称: (+)-利卡灵
• 英文名称: licarin B
• 英文别名: (-)-Licarin；5-[(2S,3S)-7-methoxy-3-methyl-5-[(E)-prop-1-enyl]-2,3-dihydro-1-benzofuran-2-yl]-1,3-benzodioxole
• CAS: 42016-15-9
• 化学式: C₂₀H₂₀O₄
• 分子量: 324.376
• InChiKey: DMMQXURQRMNSBM-NSWCWGQASA-N

物化性质

• 沸点：
  428.5±45.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-利卡灵 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 生成 (8R)-4'-hydroxy-5'-methoxy-3,4-methylenedioxy-8,3'-neolignan
  参考文献：
  名称：

  来自 Aniba lancifolia 的新木脂素

  摘要：

  灌木Aniba lancifolia Kubitzki et Rodrigues (Lauraceae) 的枝条除了含有2-羟基-4,5-二甲氧基烯丙苯及其二聚体环己-2-烯丙基-5-en-4,5-二甲氧基-4-O-(2' -allyl-4',5'-dimethoxyphenyl)-1-one (lancilin, 2) 6 种其他新型新木脂素：(4S,2'R)- 和 (4R,2'E)-cyclohexan-2-allyl-2， 5-二烯-4,5-二甲氧基-4-[2'-(1'-愈创木酰基)-丙基]-1-one (lancifolins A and B, 3a and 3b), (4S,2'R)- 和 ( 4R,2'R)-环己基-2-烯丙基-2,5-二烯-4,5-二甲氧基-4-[2'-(1'-藜芦基)-丙基]-1-酮(lancifolins C和D， 3c和3d)、(4S,2'R)-和(4R

  DOI：

  10.1016/s0031-9422(00)81975-5
• 作为产物：
  描述：

  2-Ethyl-6-methoxy-4-<(E)-prop-1-enyl>phenyl N,N,N',N'-tetramethylphosphorodiamidate 在 lithium aluminium tetrahydride 、 四甲基乙二胺 、 仲丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (+)-利卡灵
  参考文献：
  名称：

  A Regioselective Lithiation of ortho-Cresols Using the Bis(dimethylamino)phosphoryl Group as a Directing Group: General Synthesis of 2,3-Dihydrobenzo(b)furans Including Naturally Occurring Neolignans.

  摘要：

  作为关键步骤，通过对原甲苯基四甲基磷二酰胺进行区域选择性石化作用，然后加入芳香醛，开发了一种 2-芳基-2，3-二氢苯并[b]呋喃的通用合成方法。生成的二硫代锂与芳香醛反应，得到 1，2-二硫代乙醇衍生物。用氢化铝锂还原去除磷基，然后进行酸处理，可得到 2-芳基-2，3-二氢苯并[b]呋喃，总产率很高。在以 O-双（二甲基氨基）磷酸化丁香酚或异丁香酚为起始物，对 (±)-licarin B 和 (±)-carnatol 等高度取代的新木犀草素天然产物进行区域选择性合成时，证明了这一策略的实用性。

  DOI：

  10.1248/cpb.39.3123

文献信息

• Neolignans from Myristica fragrans seeds, revision of their absolute configurations, reduction products and biological activities
  作者：Sudarat Kruakaew、Suriphon Singha、Ek Sangvichien、Jantana Yahuafai、Somyote Sutthivaiyakit

  DOI：10.1016/j.phytochem.2022.113174

  日期：2022.7

  tetrahydrogenated products, the absolute configuration of these compounds was thoroughly investigated based on their optical rotations and ECD spectra. This report provides evidences concerning the disagreement between the use of an aromatic quadrant rule and time-dependent density function theory calculation for the prediction of the absolute configurations at C-7 and C-8 in these dihydrobenzofuran

  肉豆蔻CH 2 Cl 2提取物的色谱纯化种子提供了 19 种已知化合物，其中分离出 4 种二氢呋喃新木脂素，即 licarines A、B 和 maceneolignan A、B。在氢化之前，为了获得它们的二氢化和四氢化产物，这些化合物的绝对构型基于它们的旋光度和 ECD 光谱进行了彻底的研究。该报告提供了关于使用芳香象限规则和时间相关的密度函数理论计算来预测这些二氢苯并呋喃新木脂素中 C-7 和 C-8 的绝对构型之间存在分歧的证据。随后重新定义了 licarines A、B 和 maceneolignans A、B 的绝对构型。还研究了 licarines A、B 和 maceneoligans A、B 的分离物和还原产物的抗菌和细胞毒活性。
• Synthesis of (±)-licarin B and eupomatenoids-1 and -12: A general approach to 2-aryl-7-alkoxy-benzofuranoid neolignans
  作者：Thomas A Engler、Wenying Chai

  DOI：10.1016/0040-4039(96)01619-x

  日期：1996.9

  New syntheses of the title compounds are described using Lewis acid-promoted reactions of styrenes with N-phenylsulfonyl-1,4-benzoquinone monoimines to regioselectively form the 2-arylbenzofuranoid ring system followed by conversion of the aromatic N-phenylsulfonyl moiety into a propenyl substituent. Copyright (C) 1996 Elsevier Science Ltd
• Neolignans from Magnolia kachirachirai
  作者：Kazuo Ito、Kazuhiko Ichino、Toshiyuki Iida、Jengshiow Lai

  DOI：10.1016/s0031-9422(00)84117-5

  日期：1984.1
• Neolignans from Aniba lancifolia
  作者：Pedro S.P. Diaz、Massayoshi Yoshida、Otto R. Gottlieb

  DOI：10.1016/s0031-9422(00)81975-5

  日期：1980.1

  The branches of the shrub Aniba lancifolia Kubitzki et Rodrigues (Lauraceae) contain besides 2-hydroxy-4,5- dimethoxyallylbenzene and its dimer cyclohexan-2-allyl- 5-en-4,5-dimethoxy-4-O-(2′-allyl-4′,5′-dimethoxyphenyl)-1-one (lancilin, 2) 6 further novel neolignans: (4S,2′R)- and (4R,2′E)-cyclohexan-2-allyl-2,5-dien-4,5-dimethoxy-4-[2′-(1′-guaiacyl)-propyl]-1-one (lancifolins A and B, 3a and 3b),

  灌木Aniba lancifolia Kubitzki et Rodrigues (Lauraceae) 的枝条除了含有2-羟基-4,5-二甲氧基烯丙苯及其二聚体环己-2-烯丙基-5-en-4,5-二甲氧基-4-O-(2' -allyl-4',5'-dimethoxyphenyl)-1-one (lancilin, 2) 6 种其他新型新木脂素：(4S,2'R)- 和 (4R,2'E)-cyclohexan-2-allyl-2， 5-二烯-4,5-二甲氧基-4-[2'-(1'-愈创木酰基)-丙基]-1-one (lancifolins A and B, 3a and 3b), (4S,2'R)- 和 ( 4R,2'R)-环己基-2-烯丙基-2,5-二烯-4,5-二甲氧基-4-[2'-(1'-藜芦基)-丙基]-1-酮(lancifolins C和D， 3c和3d)、(4S,2'R)-和(4R
• A Regioselective Lithiation of ortho-Cresols Using the Bis(dimethylamino)phosphoryl Group as a Directing Group: General Synthesis of 2,3-Dihydrobenzo(b)furans Including Naturally Occurring Neolignans.
  作者：Mituaki WATANABE、Kenji KAWANISHI、Ryuji AKIYOSHI、Sunao FURUKAWA

  DOI：10.1248/cpb.39.3123

  日期：——

  A general synthetic method was developed for 2-aryl-2, 3-dihydrobenzo[b]furans via regioselective lithiation of ortho-tolyl tetramethylphosphorodiamidates followed by addition of aromatic aldehydes as a key step. ortho-Tolyl tetramethylphosphorodiamidates were regioselectively lithiated with sec-BuLi in tetrahydrofuran at -105°C to give benzylic lithio species. The resulting lithio species were reacted with aromatic aldehydes to provide 1, 2-diarylethanolderivatives. Reductive removal of the phosphoryl group with lithium aluminum hydride followed by acidic treatment led to 2-aryl-2, 3-dihydrobenzo[b]furans in good overall yields. The utility of this strategy was demonstrated in regioselective syntheses of highly substituted neolignan natural products, such as (±)-licarin B and (±)-carnatol, starting from O-bis(dimethylamino)phosphorylated eugenol or isoeugenol.

  作为关键步骤，通过对原甲苯基四甲基磷二酰胺进行区域选择性石化作用，然后加入芳香醛，开发了一种 2-芳基-2，3-二氢苯并[b]呋喃的通用合成方法。生成的二硫代锂与芳香醛反应，得到 1，2-二硫代乙醇衍生物。用氢化铝锂还原去除磷基，然后进行酸处理，可得到 2-芳基-2，3-二氢苯并[b]呋喃，总产率很高。在以 O-双（二甲基氨基）磷酸化丁香酚或异丁香酚为起始物，对 (±)-licarin B 和 (±)-carnatol 等高度取代的新木犀草素天然产物进行区域选择性合成时，证明了这一策略的实用性。