英西卡林 | 20628-09-5

• 物质功能分类: 天然产物 - 酚类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 中文名称: 英西卡林
• 英文名称: encecalin
• 英文别名: 1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethanone；6-acetyl-7-methoxy-2,2-dimethylchromene；encecolin；1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-ethanone；6-acetyl-2,2-dimethyl-7-methoxy-2H-benzo[b]pyran；1-(7-methoxy-2,2-dimethylchromen-6-yl)ethanone
• CAS: 20628-09-5
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: WXVLCNREBFDEKS-UHFFFAOYSA-N

物化性质

• 沸点：
  367.7±42.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)
• 保留指数：
  1829

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090
• 储存条件：
  存储条件：2-8℃，干燥，密闭。

制备方法与用途

恩卡林是一种天然的苯并呋喃化合物。

反应信息

• 作为反应物：
  描述：

  英西卡林 在 ammonium acetate 、 sodium cyanoborohydride 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 16.17h， 生成 N-[1-(7-methoxy-2,2-dimethyl-2H-chromen-6-yl)ethyl]-2-phenylacetamide
  参考文献：
  名称：

  Natural Product Derived Antiprotozoal Agents: Synthesis, Biological Evaluation, and Structure–Activity Relationships of Novel Chromene and Chromane Derivatives

  摘要：

  Various natural products with the chromane and chromene scaffold exhibit high antiprotozoal activity. The natural product encecalin (7) served as key intermediate for the synthesis of different ethers 9, amides 11, and amines 12. The chromane analogues 14 and the phenols 15 were obtained by reductive amination of ketones 13 and 6, respectively. Angelate 3, ethers 9, and amides 11 did not show considerable antiprotozoal activity. However, the chromene and chromane derived amines 12, 14, and 15 revealed promising antiprotozoal activity and represent novel lead compounds. Whereas benzylamine 12a and a-methylbenzylamine 12g were active against P. falciparum with IC50 values in the range of chloroquine, the analogous phenols 15a and 15b were unexpectedly 10- to 25-fold more potent than chloroquine with selectivity indexes of 6760 and 1818, respectively. The phenylbutylamine 14d based on the chromane scaffold has promising activity against T. brucei rhodesiense and L. donovani.

  DOI：

  10.1021/jm401007p
• 作为产物：
  描述：

  6-acetyl-7-hydroxy-2,2-dimethylchroman-4-one 在 4-甲基苯磺酸吡啶 、 aluminum isopropoxide 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 英西卡林
  参考文献：
  名称：

  Heterocycles from Diacetyl Phenols: Synthesis of Benzodioyrans, Acetylchromenes and Pyrano[1,2]benzisoxazoles

  摘要：

  DOI：

  10.3987/com-88-s135

文献信息

• An elegant synthesis of some naturally occurring linear acetylchromenes: eupatoriochromene, methyleupatoriochromene (encecalin); evodionol and methylevodionol
  作者：V.K. Ahluwalia、Chandra Prakash、Ranjna Gupta

  DOI：10.1016/0040-4020(82)80200-7

  日期：1982.1

  An elegant synthesis of linear acetylchromenes, viz eupatoriochromene, methyleupatoriochromene (encecalin), evodionol and methlevodionol, has been achieved by blocking the reactive position position C-3 of the appropriate ketones with an iodo group, prenylation with 3-chloro-3-methylbut-1-yne and subsequent cyclisation. Regiospecific introduction of C-prenyl group in the less reactive C-5 has been

  通过用碘基团封闭适当的酮的反应位置C-3并与3-氯-3-甲基丁烯基进行异戊烯基化，可以实现线性乙酰基色烯，即紫杉萜烯，甲基紫檀烯（encecalin），evodionol和甲基levodionol的精巧合成。 1-炔和随后的环化。通过适当的3-碘代酮与2-甲基丁-3-烯-2-醇的反应已经实现了C-异戊烯基在反应性较低的C-5中的区域特异性引入。5-异戊烯基酮也是合成线性乙酰基色烯的重要中间体。
• Acylations of 2,2-Dimethyl-2<i>H</i>-chromenes
  作者：Seiji Yamaguchi、Satoru Yamamoto、Shoichi Abe、Yoshiyuki Kawase

  DOI：10.1246/bcsj.57.442

  日期：1984.2

  Orientation in acylation reactions of 2,2-dimethyl-2H-chromenes was studied. Five acetylchromenes were obtained with two methods and six formylchromenes were obtained with a third method. Demethylation of four acyl-methoxy-substituted chromenes gave the corresponding acylchromenols. 2,2-Dimethyl-2H-chromene-6-carboxylic acid (anofinic acid) was also obtained by oxidation of 6-formylchromene.

  研究了 2,2-二甲基-2H-苯酰化反应中的定向。通过两种方法得到了五个乙酰基苯并通过第三种方法得到了六个甲酰基苯并。四种酰基甲氧基取代色烯的脱甲基反应得到了相应的酰基色酚。通过 6-甲酰基色烯的氧化作用，还得到了 2,2-二甲基-2H-色烯-6-羧酸（anofinic acid）。
• A new electrosynthesis of 2,2-dimethylchromenes from 2-(1-bromo-1-methylethyl)benzofurans
  作者：Masao Tsukayama、Hideyuki Utsumi、Akira Kunugi

  DOI：10.1039/c39950000615

  日期：——

  Electrolytic reduction of 2-(1-bromo-1-methylethyl)benzofurans in acetonitrile affords the corresponding 2,2-dimethylchromenes in good yields even in the absence of a proton donor and comprises the cleavage of a carbon–bromine bond followed by ring expansion.

  即使在没有质子供体的情况下，2-(1-溴-1-甲基乙基)苯并呋喃在乙腈中电解还原也能以良好的产率得到相应的2,2-二甲基色烯，并且包括碳-溴键的断裂和环扩展。
• Photochemistry of 7-acetoxybenzopyran derivatives. Synthesis of eupatoriochromene and encecalin
  作者：Miguel A. Miranda、Jaime Primo、Rosa Tormos

  DOI：10.1016/s0040-4020(01)89221-8

  日期：1989.1

  The photolysis of the 7-acetoxybenzopyran derivatives 1a-5a has been carried out. Chromene 1a was found to undergo extensive photopolymerization. Chromanone 2a underwent a rather inefficient photo-Fries rearrangement to the 6 - and 8 - acetyl derivatives 2b and 2c. Diacetoxychromene 3a gave the unsaturated ketone 8 as the main product, besides its deacetylation analogue 9 and chromanone 11. Diacetoxychroman

  7-乙酰氧基苯并吡喃衍生物1a-5a的光解已经进行。发现Chromene 1a进行了广泛的光聚合。Chromanone 2a经历了效率低下的Photo-Fries重排反应，生成6-和8-乙酰基衍生物2b和2c。Diacetoxychromene图3a，得到不饱和酮8作为主要产物，除了它的脱乙酰化类似物9和二氢吡喃酮11。二乙酰氧基铬烷4a提供了四种C-乙酰基产物的混合物：1b，1c，2b和2c，以及Chromene 1a和苯并二氢吡喃酮2a。最后，苯并二氢吡喃5a的辐射产生了两种可能的光炸产物5b（43％）和5c（52％）的混合物。讨论了以上结果的机理意义，特别强调了与吡喃环，烯醇酯和苄基酯部分相比，苯酯的光反应性。这些转化的合成应用通过制备紫杉烯酮1b和encecalin 1e进行了说明。
• The oligomerization and acylation of precocene I
  作者：Braulio M. Fraga、Inmaculada Cabrera

  DOI：10.1016/j.tet.2016.10.046

  日期：2016.12

  Lewis acids has been studied. In this way, the reaction of this chromene with HCl/MeOH gave two dimers, a trimer, a linear tetramer and a mixture of pentamers, whilst with FeCl3/HOAc a dimer and six cyclic tetramers were obtained. The cyclization of linear tetramers occurs between C-4‴ and C-6 or, in lower yield, between C-4‴ and C-8. In the formation of linear tetramers the C-8 functionalization was

  已经研究了前烯茂I与Brönsted和Lewis酸的低聚反应。以这种方式，该色烯与HCl / MeOH的反应产生了两个二聚体，一个三聚体，一个线性四聚体和一个五聚体的混合物，而与FeCl 3 / HOAc一起获得了一个二聚体和六个环状四聚体。线性四聚体的环化发生在C-4′和C-6之间，或者以较低的产率在C-4′和C-8之间发生。在线性四聚体的形成中，未检测到C-8官能化，这可能表明它在环化过程中发生。此外，在用FeCl 3 / HOAc处理前茂世I中也观察到氧化单电子偶联反应。另一方面，前十烯I与FeCl 3 / Ac 2的反应O产生6-酰化，产生天然色烯恩斯卡林。