sacidumlignan A | 848986-16-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: sacidumlignan A
• 英文别名: 5-(4-hydroxy-3,5-dimethoxyphenyl)-1,3-dimethoxy-6,7-dimethylnaphthalen-2-ol
• CAS: 848986-16-3
• 化学式: C₂₂H₂₄O₆
• 分子量: 384.429
• InChiKey: NBOWNYPCCMRIJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  sacidumlignan A 、 碘甲烷 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以15 mg的产率得到1,2,3-Trimethoxy-6,7-dimethyl-5-(3,4,5-trimethoxyphenyl)naphthalene
  参考文献：
  名称：

  Lignans and Their Degraded Derivatives from Sarcostemma acidum

  摘要：

  Four lignans, sacidumlignans A-D (1-4), and two degraded lignan derivatives, sacidumols A (5) and B (6), along with four known compounds, (+)-pinoresinol, 9alpha-hydroxypinoresinol, perforatic acid, and peucenine-7-O-methyl ether, were isolated from the ethanolic extract of the whole plant of Sarcostemma acidum. The structures and relative configuration of these new compounds were elucidated on the basis of spectroscopic and chemical data, especially 2D NMR techniques. Sacidumlignan D (4) was assigned as a rearranged tetrahydrofuran lignan with an unprecedented skeleton. Sacidumlignan A (1) showed moderate antimicrobial activities against two Gram-positive bacteria in vitro.

  DOI：

  10.1021/np049681s
• 作为产物：
  描述：

  5,5-bis(4-(benzyloxy)-3,5-dimethoxyphenyl)-4-methyldihydrofuran-2(3H)-one 在 lithium aluminium tetrahydride 、 palladium 10% on activated carbon 、 氢气 、 对甲苯磺酸 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 35.0h， 生成 sacidumlignan A
  参考文献：
  名称：

  的（±）全合成-sacidumlignans d和A至野鹳自由基环化反应†

  摘要：

  使用α-溴缩醛21的Ueno-Stork自由基环化作为关键步骤，已成功实现了（±）-saturumumlignan D（4）的高效合成。已经详细讨论了对称的二芳基酮19的两种合成方法。值得注意的是，sacidumlignan A（1）还可以仅以7个步骤有效地合成，总收率为25％，其中酸触发的串联反应（从类似的Ueno-Stork环化产物27开始）起了重要作用。此外，可以实现从（±）-saturumlignan D（4）到saturumlignan A（1）的潜在仿生转化。

  DOI：

  10.1039/c3ob00053b

文献信息

• Triflimide-catalyzed allylsilane annulations of benzylic alcohols for the divergent synthesis of indanes and tetralins
  作者：Jordan C. T. Reddel、Weiwei Wang、Kalli Koukounas、Regan J. Thomson

  DOI：10.1039/c6sc04762a

  日期：——

  development of a triflimide-catalyzed annulation of benzylic alcohols with allylsilanes for the synthesis of indane or tetralin structures is reported. In this fragment coupling reaction, complexity is built rapidly from readily available starting materials to yield diverse sets of products with up to three contiguous stereocenters. Indanes or tetralins can be generated from common precursors depending

  据报道，用三氟甲酰亚胺催化的苄醇与烯丙基硅烷的环合反应可用于茚满或四氢化萘结构的合成。在这种片段偶联反应中，从容易获得的起始原料迅速建立了复杂性，以产生具有多达三个连续立体中心的多种产品。取决于所使用的烯丙基硅烷试剂的结构，茚满或四氢化萘可以从常见的前体中生成。几种木脂素天然产物的简洁合成突显了这种新设计方法的实用性。
• Total Synthesis of (−)-Sacidumlignans B and D
  作者：Jeetendra Kumar Rout、C. V. Ramana

  DOI：10.1021/jo2021696

  日期：2012.2.3

  The first total synthesis of naturally occurring sacidumlignans A (1), B (2), and D (4) was executed and the absolute configuration of 2 and 4 was determined. A diastereoselective alpha- methylation of a lactone was used as the key step for the control of the chiral centers of the central lignan core. An acid mediated dehydrative cyclization of an aldehyde to construct the dihydronaphthalene unit of 2 and the aromatization of the intermediate dihydronaphthalene derivative to synthesize 1 are the key reactions employed in this regard.
• Total synthesis of (±)-sacidumlignans D and A through Ueno–Stork radical cyclization reaction
  作者：Jian-Jian Zhang、Chang-Song Yan、Yu Peng、Zhen-Biao Luo、Xiao-Bo Xu、Ya-Wen Wang

  DOI：10.1039/c3ob00053b

  日期：——

  Efficient synthesis of (±)-sacidumlignan D (4) has been successfully achieved employing Ueno–Stork radical cyclization of α-bromo acetal 21 as a key step. Two synthetic approaches for the symmetrical diaryl ketone 19 have been discussed in detail. Notably, sacidumlignan A (1) can be also efficiently synthesized in only 7 steps with 25% overall yield, where acid triggered tandem reaction starting from

  使用α-溴缩醛21的Ueno-Stork自由基环化作为关键步骤，已成功实现了（±）-saturumumlignan D（4）的高效合成。已经详细讨论了对称的二芳基酮19的两种合成方法。值得注意的是，sacidumlignan A（1）还可以仅以7个步骤有效地合成，总收率为25％，其中酸触发的串联反应（从类似的Ueno-Stork环化产物27开始）起了重要作用。此外，可以实现从（±）-saturumlignan D（4）到saturumlignan A（1）的潜在仿生转化。
• Lignans and Their Degraded Derivatives from <i>Sarcostemma </i><i>a</i><i>cidum</i>
  作者：Li-She Gan、Sheng-Ping Yang、Cheng-Qi Fan、Jian-Min Yue

  DOI：10.1021/np049681s

  日期：2005.2.1

  Four lignans, sacidumlignans A-D (1-4), and two degraded lignan derivatives, sacidumols A (5) and B (6), along with four known compounds, (+)-pinoresinol, 9alpha-hydroxypinoresinol, perforatic acid, and peucenine-7-O-methyl ether, were isolated from the ethanolic extract of the whole plant of Sarcostemma acidum. The structures and relative configuration of these new compounds were elucidated on the basis of spectroscopic and chemical data, especially 2D NMR techniques. Sacidumlignan D (4) was assigned as a rearranged tetrahydrofuran lignan with an unprecedented skeleton. Sacidumlignan A (1) showed moderate antimicrobial activities against two Gram-positive bacteria in vitro.