(2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one | 88775-47-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• 英文别名: (E)-1-(3',4'-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-1-(3,4-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one；(2E)-1-(1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)-2-propen-1-one；3,4,5-trimethoxy-3',4'-methylenedioxychalcone；1-benzo[1,3]dioxol-5-yl-3-(3,4,5-trimethoxy-phenyl)-propenone；(E)-1-(1,3-benzodioxol-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
• CAS: 88775-47-7
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: UDHVYWAGOFBWLU-GQCTYLIASA-N

物化性质

• 熔点：
  146-148 °C
• 沸点：
  519.3±50.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one 在 RaNi 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氟化硼乙醚 、 氢气 、 乙酸酐 、 potassium hydrogencarbonate 、 对甲苯磺酸 、 乙酰氯 、 lithium diisopropyl amide 、 sodium nitrite 作用下， 以 四氢呋喃 、 甲醇 、 硝基甲烷 、 乙醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 、 甲苯 为溶剂， -78.0~40.0 ℃ 、275.79 kPa 条件下， 反应 25.58h， 生成 (+/-) epipodophyllotoxin
  参考文献：
  名称：

  Total synthesis of (±) epipodophyllotoxin via a (3 + 2)-cycloaddition strategy

  摘要：

  DOI：

  10.1016/s0040-4039(00)84725-5
• 作为产物：
  描述：

  胡椒环 在 sodium hydroxide 、 zinc(II) chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 16.0h， 生成 (2E)-1-(2H-benzo[3,4-d]1,3-dioxolan-5-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis and characterization of novel benzo[d][1,3]dioxole gathered pyrazole derivatives and their antimicrobial evaluation

  摘要：

  DOI：

  10.1007/s00044-014-0952-x

文献信息

• Studies on the chemical constituents of rutaceous plants. XLIX. Development of a versatile method for the synthesis of antitumor-active benzo(c)phenanthridine alkaloids. 1. Preparation of various 2,4-bisaryl-4-oxobutyronitriles and 2,4-bisaryl-4-oxobutyramides.
  作者：HISASHI ISHII、TSUTOMU ISHIKAWA、TAKEO DEUSHI、KENICHI HARADA、TOSHIKO WATANABE、ETSUKO UEDA、TOSHIAKI ISHIDA、MITSUGI SAKAMOTO、ERI KAWANABE、TSUTOMU TAKAHASHI、YUHICHIRO ICHIKAWA、KAZUE TAKIZAWA、TAKESHI MASUDA、IHSHENG CHEN

  DOI：10.1248/cpb.31.3024

  日期：——

  For the sake of establishment of a versatile synthetic method for benzo [c] phenanthridine alkaloids, improvement of the Robinson synthetic method was examined. Thirteen chalcones (7a-m) were prepared by condensation of two acetophenone derivatives (15 and 16) with eleven benzaldehyde derivatives (19a-k) as fundamental starting materials. Hydrocyanation of these chalcones (7a-l) except one (7m) gave the corresponding 2, 4-bisaryl-4-oxobutyronitriles (8a-l). Eleven 2, 4-bisaryl-4-oxobutyramides (9a-k) were also prepared.

  为了建立一种通用的苯并[c]菲啶生物碱合成方法，对Robinson合成方法进行了改进。通过将两个乙酰苯衍生物（15和16）与十一种苯甲醛衍生物（19a-k）缩合，制备了十三种查尔酮（7a-m）作为基本起始材料。除了一个查尔酮（7m）外，这些查尔酮（7a-l）的氰化反应得到了相应的2,4-双芳基-4-氧代丁腈（8a-l）。还制备了十一种2,4-双芳基-4-氧代丁酰胺（9a-k）。
• Total synthesis of (±)-picropodophyllone
  作者：William S. Murphy、Sompong Wattanasin

  DOI：10.1039/p19820000271

  日期：——

  Following model studies, the synthesis of (±)-picropodophyllone was completed by first cyclopropanating the appropriate chalcone (11) with ethoxycarbonyl dimethylsulphonium methylide. Treatment of the resulting cyclopropyl ketone with stannic chloride in either benzene or methylene chloride failed but in nitromethane the tetralone (1Oa) was formed. The lactose ring was completed using formaldehyde

  根据模型研究，首先通过将合适的查尔酮（11）与乙氧基羰基二甲基甲磺酸甲酯环丙烷化，完成（±）-鬼臼苦素的合成。用氯化锡在苯或二氯甲烷中处理所得的环丙基酮失败，但在硝基甲烷中形成四氢萘酮（10a）。使用甲醛完成乳糖环，基于查尔酮的总产率为40％。
• An improved route to an intermediate in podophyllotoxin synthesis
  作者：William S. Murphy、Sompong Wattanasin

  DOI：10.1039/c39800000262

  日期：——

  cyclopropanyl keto-ester epimers (4) and (5); both stannic chloride and boron trifluoride etherate in nitromethane catalyse the stereoselective cyclisation of this mixture to the tetralone (2), the known podophyllotoxin precursor, in 51% overall yield.

  用二甲基磺酸乙氧基羰基甲基酯将查耳酮（3）环丙烷化，得到环丙烷基酮酯差向异构体（4）和（5）的1：1混合物；氯化锡和三氟化硼在硝基甲烷中的醚化反应均催化该混合物立体选择性环化成四氢萘酮（2）（已知鬼臼毒素前体），总收率51％。
• An Improved Procedure for the Preparation of Chalcones and Related Enones
  作者：Sompong Wattanasin、William S. Murphy

  DOI：10.1055/s-1980-29155

  日期：——
• Biochemical evaluation of a series of synthetic chalcone and hydrazide derivatives as novel inhibitors of cruzain from Trypanosoma cruzi
  作者：Deise M. Borchhardt、Alessandra Mascarello、Louise Domeneghini Chiaradia、Ricardo J. Nunes、Glaucius Oliva、Rosendo A. Yunes、Adriano D. Andricopulo

  DOI：10.1590/s0103-50532010000100021

  日期：——

  Chagas' disease, a parasitic infection widely distributed throughout Latin America, is a major public health problem with devastating consequences in terms of human morbidity and mortality. The enzyme cruzain is the major cysteine protease from Trypanosoma cruzi, the etiologic agent of American trypanosomiasis or Chagas' disease, and has been selected as an attractive target for the development of novel trypanocidal drugs. In the present work, we describe the synthesis and inhibitory effects of a series of thirty-three chalcone and seven hydrazide derivatives against the enzyme cruzain from T. cruzi. Most of the compounds showed promising in vitro inhibition (IC50 values in the range of 20-60 mu M), which suggest the potential of these compounds as lead candidates for further development. Twelve compounds have not been reported before, and four of them (7, 13, 16 e 18) are among the most potent inhibitors of the series.