(1E,4E)-1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one | 1403840-45-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1E,4E)-1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohexen-1-yl)penta-1,4-dien-3-one
• CAS: 1403840-45-8
• 化学式: C₂₀H₂₃ClO
• 分子量: 314.855
• InChiKey: CHYWHLZYMPOUNA-AQASXUMVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1E,4E)-1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one 在 silica gel 作用下， 以 甲醇 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 5-o-chlorophenyl-7,11,11-trimethyltricyclo[5.4.0.0^3,6]undec-1-ene-4-one
  参考文献：
  名称：

  Induction of apoptosis by cyclobutanones and derived polycyclic γ-lactones: a preliminary analysis of antiproliferative activity

  摘要：

  一系列环丁酮（7a-f）通过在水甲醇中辐照β-离子酮衍生的查尔酮（4a-f）而合成，并通过Baeyer-Villiger氧化进一步转化为多环γ-内酯（8a-f）。

  DOI：

  10.1039/c5md00289c
• 作为产物：
  描述：

  beta-紫罗酮 、 2-氯苯甲醛 在 十六烷基三甲基溴化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 24.0h， 以50%的产率得到(1E,4E)-1-(2-chlorophenyl)-5-(2,6,6-trimethylcyclohex-1-enyl)penta-1,4-dien-3-one
  参考文献：
  名称：

  Chemotherapy of leishmaniasis part X: Synthesis and bioevaluation of novel terpenyl heterocycles

  摘要：

  Some novel alpha and beta ionone based chalcones and their dihydropyrazolidines/pyrazolidines have been synthesized and evaluated for their in vitro and in vivo antileishmanial activities against Leishmania donovani. Amongest all, one compound (4d) exhibited significant in vitro activity against intracellular amastigotes of Leishmania donovani with IC50 values of 7.49 mu M and was found promising as compared to reference drug, miltefosine. On the basis of good Selectivity Index (S.I.), the compound was further tested for its in vivo response against Leishmania donovani/hamster model and has shown significant inhibition of parasite multiplication (81%). The present study has helped us in identifying a new lead that could be exploited as a potential antileishmanial agent. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.110

文献信息

• Photochemical formation and decomposition of 8-[β-arylethenyl]-2,2,6-trimethyl-7,9,10-trioxa-tricyclo[6.2.2.01,6]dodec-11-ene to novel 6-hydroxy-1,7,7-trimethyl-2-oxa-bicyclo[4.4.0]dec-4-en-3-one in the presence of oxygen
  作者：Vishal Sharma、Vivek Gupta、Sumati Anthal、Ajit K. Saxena、Mohan Paul S. Ishar

  DOI：10.1016/j.tetlet.2012.08.028

  日期：2012.10

  Irradiation of (E,E)-arylidene-β-ionones in the presence of oxygen leads to the formation of 8-[β-arylethenyl]-2,2,6-trimethyl-7,9,10-trioxa-tricyclo[6.2.2.01,6]dodec-11-enes (3). However, prolonged irradiation in the presence of oxygen leads to their conversion to 6-hydroxy-1,7,7-trimethyl-2-oxa-bicyclo[4.4.0]dec-4-en-3-one (4), apparently proceeding through addition of oxygen to the side chain π-bond

  （照射E，E [β）-arylidene-β-紫罗兰酮在氧引线的存在，以8-形成- arylethenyl] -2,2,6-三甲基- 7,9,10-三氧杂-三环[6.2 .2.0 1,6 ] dodec-11-enes（3）。但是，在氧存在下长时间照射会导致其转化为6-羟基-1,7,7-三甲基-2-氧杂双环[4.4.0] dec-4-en-3-one（4）通过向3中的侧链π键添加氧来进行