(1S)-1-(3,4,5-trimethoxyphenyl)but-3-en-1-ol | 1152182-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S)-1-(3,4,5-trimethoxyphenyl)but-3-en-1-ol
• CAS: 1152182-34-7
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: SISDYNVDFJAPLB-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S)-1-(3,4,5-trimethoxyphenyl)but-3-en-1-ol 、 (E)-4-(3-(4-bromophenyl)-3-oxo-propenyl)benzaldehyde 、 对甲苯磺酸 以 氯仿 、 水 为溶剂， 以72%的产率得到(2R,4S,6S)-2-(3,4,5-trimethoxyphenyl)-6-(4-((E)-3-(4-bromophenyl)-3-oxo-propenyl)phenyl)-4-tosyloxy tetrahydropyran
  参考文献：
  名称：

  Synthesis of flavonoids based novel tetrahydropyran conjugates (Prins products) and their antiproliferative activity against human cancer cell lines

  摘要：

  Following our previously reported Prins cyclization strategy, a series of novel and highly functionalized flavonoid based THPs (Prins products) were designed, synthesized and evaluated for their anti-proliferative activity. Novel products were afforded in excellent yields (72-96%) within 20-90 min at 62 degrees C using flavonoid aldehydes, homoallylic alcohols, p-TSA center dot H2O (catalyst and reagent) and MS 4 angstrom in CHCl3. Deprotection of tosyl group was achieved with TFA (catalyst and solvent) at 140 degrees C to obtain 4-hydroxytetrahydropyrans and further reaction of 4-hydroxytetrahydropyrans with cinnamoyl chloride afforded 4-cinnamate tetrahydropyrans under neat condition. Synthesized compounds evaluated against human cancer cell lines (Hep3 beta, MCF-7 and Hela), have shown moderate to good antiproliferative activity in vivo. Compounds 3q and 3zb exhibited similar cytotoxicity (IC50 6.6 +/- 1.4, 6.9 +/- 1.0 mu M, respectively) to the reference drug doxorubicin (IC50 7.6 +/- 0.9 mu M) against the MCF-7 cancer cell line. Compound 3zb was found equally active as the standard drug (IC50 4.48 +/- 2.1 mu M) against the Hep3 beta cell line and compounds 3c and 3q showed moderate cytotoxicity (IC50 10.40 +/- 1.1, 12.9 +/- 1.7 mu M, respectively) against the HeLa cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.033
• 作为产物：
  描述：

  丙烯基三氯硅烷 、 3,4,5-三甲氧基苯甲醛 在 N,N-二甲基丙烯基脲 、 C₂₂H₂₆N₂O₄ 、 水 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 25.0h， 生成 (1R)-1-(3,4,5-trimethoxyphenyl)but-3-en-1-ol 、 (1S)-1-(3,4,5-trimethoxyphenyl)but-3-en-1-ol
  参考文献：
  名称：

  Development of chiral dinitrones as modular Lewis base catalysts: asymmetric allylation of aldehydes with allyltrichlorosilanes

  摘要：

  Chiral dinitrones were synthesized by the condensation of a C-2-symmetrical chiral dihydroxylamine with various aldehydes. The electronic and steric properties of the dinitrones can be modified by changing the aldehyde component. The activity of dinitrones as Lewis base catalysts was examined for the asymmetric allylation of aldehydes with allyltrichlorosilanes. Using DMPU as an additive in chloroform, the reaction proceeded at room temperature to afford allylated products in good yields and good enantioselectivities. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.05.048

文献信息

• Ti-Catalyzed Barbier-Type Allylations and Related Reactions
  作者：Rosa E. Estévez、José Justicia、Btissam Bazdi、Noelia Fuentes、Miguel Paradas、Duane Choquesillo-Lazarte、Juan M. García-Ruiz、Rafael Robles、Andreas Gansäuer、Juan M. Cuerva、J. Enrique Oltra

  DOI：10.1002/chem.200802180

  日期：2009.3.9

  Versatility of titanium: Titanocene(III) complexes catalyze Barbier‐type allylations, intramolecular crotylations (cyclizations), and prenylations of a wide range of aldehydes and ketones. These reactions take place at RT under mild conditions compatible with many functional groups; provide good yields of open‐chain and cyclic homoallylic alcohols, including heterocyclic derivatives; and can be conducted

  钛的通用性：钛茂（III）配合物催化Barbier型烯丙基化，分子内crotylations（环化）和各种醛和酮的异戊烯基化。这些反应在室温下与许多官能团相容的温和条件下进行。提供高收率的开链和环状均丙醇，包括杂环衍生物；并且可以通过使用对映体纯的钛催化剂来对映选择性地进行。