trans-1,4,5-trimethoxy-2-(3'-methoxycarbonylprop-1'-enyl)naphthalene | 79386-34-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-1,4,5-trimethoxy-2-(3'-methoxycarbonylprop-1'-enyl)naphthalene
• 英文别名: methyl (E)-4-(1,4,5-trimethoxynaphthalen-2-yl)but-3-enoate；methyl (E)-4-(1,4,5-trimethoxynaphth-2-yl)-3-butenoate
• CAS: 79386-34-8
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: KFPOOMXKIPXDCQ-FNORWQNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  trans-1,4,5-trimethoxy-2-(3'-methoxycarbonylprop-1'-enyl)naphthalene 在 甲基磺酰胺 、 AD-mix-β 、 copper(II) bis(trifluoromethanesulfonate) 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 16.0h， 生成
  参考文献：
  名称：

  A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and epi-(+)-Frenolicin B Synthesis

  摘要：

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

  DOI：

  10.1021/ol4027649
• 作为产物：
  描述：

  1,5-二羟基萘 在 吡啶 、 sodium dithionite 、 二(三叔丁基膦)钯 、 N-甲基二环己基胺 、 四丁基溴化铵 、 水 、 对甲苯磺酸 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 62.84h， 生成 trans-1,4,5-trimethoxy-2-(3'-methoxycarbonylprop-1'-enyl)naphthalene
  参考文献：
  名称：

  A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and epi-(+)-Frenolicin B Synthesis

  摘要：

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.

  DOI：

  10.1021/ol4027649

文献信息

• PYRANONAPHTHOQUINONE COMPOUNDS AND METHODS OF USE THEREOF
  申请人：University of Kentucky Research Foundation

  公开号：US20180055816A1

  公开（公告）日：2018-03-01

  Provided herein are pyranonaphthoquinone compounds and methods of using pyranonaphthoquinone compounds. The method of using the pyranonaphthoquinone compounds includes selectively inhibiting 4E-BP1 phosphorylation by administering at least one pyranonaphthoquinone or pyranonaphthoquinone analog to a subject in need thereof. The pyranonaphthoquinone compounds includes a structure according to Formula I:

  本文提供了吡喃萘醌化合物以及使用吡喃萘醌化合物的方法。使用吡喃萘醌化合物的方法包括通过向需要的受试者施用至少一种吡喃萘醌或吡喃萘醌类似物来选择性地抑制4E-BP1的磷酸化。吡喃萘醌化合物包括符合以下式I的结构：
• Efficient Synthesis of (+)-Kalafungin and (-)-Nanaomycin D by Asymmetric Dihydroxylation, Oxa-Pictet-Spengler Cyclization, and H₂SO₄-Mediated Isomerization
  作者：Reinhard Brückner、Rodney Fernandes

  DOI：10.1055/s-2005-868505

  日期：——

  The pyranonaphthoquinone antibiotics and antitumor agents (+)-kalafungin (1) and (-)-nanaomycin D (3 = ent-1) were synthesized from 1,5-napthalenediol (13) in 11 steps. Stereocontrol was high: 99.5 ee/93% diastereoselectivity for 1, 98.5% ee/94% ­diastereoselectivity for 3. Enantiocontrol was achieved by the asymmetric dihydroxylation of the β,γ-unsaturated ester 9. Dia­stereocontrol was realized in the final step by an almost complete epimerization in H2SO4.

  通过 11 个步骤从 1,5-萘二醇（13）合成了吡喃萘醌类抗生素和抗肿瘤药物 (+)-kalafungin (1) 和 (-)-nanaomycin D (3 = ent-1)。这两种化合物的立体选择性很高：1 的非对映选择性为 99.5%，3 的非对映选择性为 98.5%。δ,δ-不饱和酯 9 的不对称二羟基化实现了对映体控制。在最后一步，通过在 H2SO4 中几乎完全的外延化反应实现了非对映控制。
• A highly enantioselective synthesis of (−)- and (+)-juglomycin A through Dötz annulation and asymmetric dihydroxylation
  作者：Rodney A. Fernandes、Vijay P. Chavan

  DOI：10.1016/j.tetlet.2008.04.059

  日期：2008.6

  A highly enantioselective synthesis of (−)- and (+)-juglomycin A, a quinone antibiotic is described. The synthesis is completed in eight steps, and 19% overall yield and in a high enantioselectivity of 99.5% [for (−)-juglomycin A] and 98.5% [for (+)-juglomycin A]. The synthetic strategy features an efficient combination of the Dötz annulation reaction and asymmetric dihydroxylation as the keys steps

  描述了对-抗生素-（-）-和（+）-珠霉素A的高度对映选择性合成。合成完成了八个步骤，总产率为19％，对映体选择性高（对（-）-珠红霉素A为99.5％[对（+）-珠红霉素A]为98.5％）。合成策略的关键步骤是有效结合Dötz环化反应和不对称二羟基化反应。
• The syntheses of (±)-juglomycin A and (±)-juglomycin B, racemates of two isomeric naturally occurring naphthoquinonoid antibiotics
  作者：Robin G. F. Giles、Peter R. K. Mitchell、Gregory H. P. Roos、Jacobus M. M. Strümpfer

  DOI：10.1039/p19810002091

  日期：——

  Syntheses of the diastereoisomeric 5-hydroxy-2-(4′-hydroxy-γ-butyrolacton-5′-yl)-1,4-naphthoquinones (1) and (2) and their 5-deoxy-analogues (3) and (4) are described. The stereochemistries of the latter, being defined through unambiguous synthesis, permit the assignment of the configurations of (1) and (2)(which were obtained from a single precursor) and also those of the natural products, juglomycins

  非对映异构体5-羟基-2-（4'-羟基-γ-丁内酯-5'-基）-1,4-萘醌（1）和（2）及其5-脱氧类似物（3）和（ 4）描述。后者的立体化学通过明确的合成定义，允许指定（1）和（2）的构型（它们是从单一前体获得的）以及天然产物朱红霉素A和B的构型。
• A Diastereoselective Oxa-Pictet–Spengler-Based Strategy for (+)-Frenolicin B and <i>epi</i>-(+)-Frenolicin B Synthesis
  作者：Yinan Zhang、Xiachang Wang、Manjula Sunkara、Qing Ye、Larissa V. Ponomereva、Qing-Bai She、Andrew J. Morris、Jon S. Thorson

  DOI：10.1021/ol4027649

  日期：2013.11

  An efficient diastereoselective oxa-Pictet - Spengler reaction strategy was developed to construct benzoisochroman diastereomers. The utility of the reaction was demonstrated in the context of both the total synthesis of naturally occurring pyranonaphthoquinones (+)-frenolicin B and epi-(+)-frenolicin B as well as a range of frenolicin precursor analogs. The method is versatile and offers exquisite stereocontrol and, as such, offers a synthetic advance for the synthesis of pyranonaphthoquinone analogs.