1-methoxy-2-(4-methylpent-3-en-1-yl)benzene | 171979-70-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-methoxy-2-(4-methylpent-3-en-1-yl)benzene
• 英文别名: 1-Methoxy-2-(4-methylpent-3-enyl)benzene
• CAS: 171979-70-7
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: UMDXKHAKVCWYID-UHFFFAOYSA-N

物化性质

• 沸点：
  257.2±9.0 °C(Predicted)
• 密度：
  0.925±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-methoxy-2-(4-methylpent-3-en-1-yl)benzene 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 4-二甲氨基吡啶 、 三氯化铝 、 三氟乙酸2,2,2-三氟乙酯 、 4 A molecular sieve 、 硫酸 、 2,4-di-t-butyl-3-methyl phenol 、 四丁基氟化铵 、 氧气 、 四甲基锡 、 三溴化硼 、 三乙胺 、 甲烷磺酰基叠氮化物 、 lithium chloride 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， -78.0~90.0 ℃ 、344.73 kPa 条件下， 反应 136.75h， 生成 隐丹参酮
  参考文献：
  名称：

  Aromatic Annulation Strategy for the Synthesis of Angularly-Fused Diterpenoid Quinones. Total Synthesis of (+)-Neocryptotanshinone, (-)-Cryptotanshinone, Tanshinone IIA, and (.+-.)-Royleanone

  摘要：

  The application of a photochemical aromatic annulation strategy in highly efficient total syntheses of several diterpenoid quinones isolated from the traditional Chinese medicine Dan Shen is reported. The pivotal step in each synthesis involves the assembly of a key tricyclic intermediate via the application of a recently developed ''second-generation'' photochemical aromatic annulation method for the construction of highly substituted aromatic systems. In the total synthesis of neocrypto-tanshinone,;the synthesis of the requisite diazo ketone annulation substrate 7 was achieved using palladium-mediated coupling reactions and an intramolecular Friedel-Crafts cyclization to form key carbon-carbon bonds. The pivotal aromatic annulation reaction was then accomplished by irradiating a solution of the diazo ketone 7 and the readily available siloxyalkyne 6 in benzene at room temperature. The desired tricyclic phenol 16 was produced in 58-65% yield and was then converted to (+)-neocryptotanshinone (1) by treatment with tetra-n-butylammonium fluoride in the presence of oxygen. Cyclization to generate (-)-cryptotanshinone (2) was accomplished in high yield by brief exposure of 1 to an ethanolic solution of concentrated sulfuric acid, and dehydrogenation of 2 with DDQ furnished tanshinone IIA (3). As a further demonstration of the utility of the photochemical aromatic annulation strategy in the construction of angularly-fused diterpenes, the total synthesis of(+/-)-royleanone (4) was also investigated. Irradiation of a solution of the diazo ketone 18 and siloxyalkyne 25 produced the tricyclic intermediate 26, which was converted in two steps to royleanone by desilylation and oxidation.

  DOI：

  10.1021/jo00131a006
• 作为产物：
  描述：

  2-溴苯甲醚 、 4-methylpent-3-enylzinc(II) bromide 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到1-methoxy-2-(4-methylpent-3-en-1-yl)benzene
  参考文献：
  名称：

  抗肿瘤剂 269. 非芳香环-A 新丹参内酯类似物，TNO，作为一类新的强效抗肿瘤剂

  摘要：

  设计、合成了四氢新丹参内酯 (TNT) 和四氢萘-1-醇 (TNO) 衍生物，并对其细胞毒活性进行了评估。发现 TNO 衍生物是一种很有前途的新型体外抗肿瘤剂。环己烯环-A 可以显着影响抗肿瘤活性和选择性。化合物20显示出最高的效力，ED 50值分别为 0.7 和 1.7 μM，分别针对 SK-BR-3 和 ZR-75-1 乳腺癌细胞系。

  DOI：

  10.1016/j.bmcl.2009.09.092

文献信息

• A Relay Strategy Actuates Pre-Existing Trisubstituted Olefins in Monoterpenoids for Cross-Metathesis with Trisubstituted Alkenes
  作者：Karim A. Bahou、D. Christopher Braddock、Adam G. Meyer、G. Paul Savage、Zhensheng Shi、Tianyou He

  DOI：10.1021/acs.joc.0c00067

  日期：2020.4.3

  benzylidene catalyzed olefin cross-metathesis with homoprenyl benzenes. Successful implementation of this approach provided several epoxypolyenes as expected (E/Z, ca. 2-3:1). The method is further generalized for the cross-metathesis of pre-existing trisubstituted olefins in other relay-actuated Δ6,7-functionalized monoterpenoid alcohols with various other trisubstituted alkenes to form new trisubstituted

  环氧多烯-底物的逆合成断开-重新连接分析，该底物可以环化为罗汉木烷型三环-揭示了中继驱动的Δ6,7-官能化单萜类醇用于钌亚苄基催化的烯烃与异戊二烯苯的交叉复分解。该方法的成功实施提供了预期的几种环氧多烯（E / Z，约2-3：1）。该方法被进一步推广用于在其他中继活化的Δ6,7-官能化单萜类醇中与预先存在的三取代烯烃与各种其他三取代烯烃的交叉复分解反应，以形成新的三取代烯烃。对映体纯净但几何形状不纯的环氧多烯底物的环氧多烯环化提供了对映体纯的，反式稠合的，罗丹烷型三轮车（来自E几何异构体）。
• Biaromatic compounds and pharmaceutical and cosmetic compositions comprising them
  申请人：Galderma Research & Development

  公开号：US06346546B1

  公开（公告）日：2002-02-12

  Biaromatic compounds connected by a propynylene or ailenylene bond, corresponding to the formula (I).

  由丙炔基或芳烃基键连接的双芳香族化合物，对应式（I）。
• Asymmetric total synthesis of (+)-isocryptotanshinone and formal synthesis of (−)-cryptotanshinone
  作者：Xiang Shi、Xiaoyu Liu、Feilong Yang、Yong Wang、Zhenwei Wang、Xiaozhen Jiao、Ping Xie

  DOI：10.1016/j.tet.2019.05.069

  日期：2019.7

  The first asymmetric total synthesis of (+)-isocryptotanshinone was achieved in 12 linear steps with 12% overall yield from commercially available dihydrobenzopyrone. The key step was a base-mediated cyclization reaction. In addition, the synthetic strategy included the formal synthesis of (−)-cryptotanshinone.

  （+）-异隐庚烷酮的第一次不对称全合成以12个线性步骤完成，从可商购的二氢苯并吡喃酮中获得的总收率为12％。关键步骤是碱基介导的环化反应。另外，合成策略包括（-）-隐丹参酮的形式合成。
• [EN] SUBSTITUTED FNO (2-[FURAN-2-YL] NAPHTHALEN-1-OL) DERIVATIVES AS ANTI-CANCER AGENTS<br/>[FR] DÉRIVÉS DE FNO (2-[FURANE-2-YL] NAPHTHALÈNE-1-OL) SUBSTITUÉS UTILISÉS COMME AGENTS ANTICANCÉREUX
  申请人：UNIV NORTH CAROLINA

  公开号：WO2010080414A3

  公开（公告）日：2010-11-04