6,6-dimethyl-2-phenyl-1,5,7-trioxaspiro[2.5]octane-4,8-dione | 167389-06-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-dimethyl-2-phenyl-1,5,7-trioxaspiro[2.5]octane-4,8-dione
• 英文别名: 6,6-dimethyl-1,5,7-trioxa-2-phenylspiro<2.5>octane-4,8-dione；6,6-Dimethyl-1-phenyl-2,5,7-trioxaspiro[2.5]octane-4,8-dione
• CAS: 167389-06-2
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: NKXYDBCVBIWVJQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-2-phenyl-1,5,7-trioxaspiro[2.5]octane-4,8-dione 、 (E)-N-benzylidenebenzenamine 在 palladium on activated charcoal 氢气 作用下， 以 苯 、 甲醇 为溶剂， 反应 4.0h， 以70%的产率得到trans-2-benzyloxy-1,4-diphenyl-β-lactam-3-carboxylic acid
  参考文献：
  名称：

  席夫碱与烯酮的环加成反应，该酮是2-芳基取代的1,5,7-三氧杂螺[2.5]辛烷-4​​,8-​​二酮的热解反应而生成的

  摘要：

  通过2-芳基取代的1,5,7-三氧杂螺[2.5]辛烷-4​​,8-​​二酮1的热解反应生成的α-氧代乙烯酮6与席夫碱2反应，得到在以下基团之间构筑的螺环化合物β-内酰胺和1,3-二氧戊环-4-酮；即2,3,6-三芳基-2-氮杂-5,7-二氧杂螺[3.4]辛烷-1,8-二酮3和4。在催化量的Pd-C存在下3a和4a混合物的氢化反应生成反式-2-苄氧基-1,4-二苯基-β-内酰胺-3-羧酸9。

  DOI：

  10.1002/jhet.5570430104
• 作为产物：
  描述：

  5-亚苄基-2,2-二甲基-1,3-二恶烷-4,6-二酮 在 双氧水 作用下， 以 乙腈 为溶剂， 生成 6,6-dimethyl-2-phenyl-1,5,7-trioxaspiro[2.5]octane-4,8-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents

  摘要：

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.033

文献信息

• Tsuno, Takashi; Sugiyama, Kunio; Ago, Hideo, Heterocycles, 1994, vol. 38, # 12, p. 2631 - 2654
  作者：Tsuno, Takashi、Sugiyama, Kunio、Ago, Hideo

  DOI：——

  日期：——
• Tsuno Takashi, Sugiyama Kunio, Ago Hideo, Heterocycles, 38 (1994) N 12, S 2631-2654
  作者：Tsuno Takashi, Sugiyama Kunio, Ago Hideo

  DOI：——

  日期：——
• Synthesis and biological evaluation of arylidene analogues of Meldrum’s acid as a new class of antimalarial and antioxidant agents
  作者：Harmeet S. Sandhu、Sameer Sapra、Mukesh Gupta、Kunal Nepali、Raju Gautam、Sunil Yadav、Raj Kumar、Sanjay M. Jachak、Manoj Chugh、Manish K. Gupta、Om P. Suri、K.L. Dhar

  DOI：10.1016/j.bmc.2010.06.033

  日期：2010.8

  A series of arylidene analogues of Meldrum's acid were synthesized and evaluated for in vitro antimalarial and antioxidant activities for the first time. The influence of various physico-chemical parameters such as dielectric constant (epsilon), donor number (DN), acceptor number (AN), hydrogen bond donor (HBD), hydrogen bond acceptor (HBA), and solubilizing power of the solvents on Meldrum's acid anion generation and thus on promoting the Knoevenagel condensation of Meldrum's acid with aryl aldehydes has been discussed. Five compounds 9l, 9m, 9n, 9r, and 9s were found to be most active against Plasmodium falciparum with IC(50) values in the range of 9.68-16.11 mu M. Compound 9l exhibited the most potent antimalarial activity (IC(50) 9.68 mu M). The compounds were also found to possess antioxidant activity when tested against DPPH and ABTS free radicals. (C) 2010 Elsevier Ltd. All rights reserved.
• Cycloaddition reaction of schiff bases with ketenes generated by pyrolysis of 2-aryl-substituted 1,5,7-trioxaspiro[2.5]octane-4,8-diones
  作者：Takashi Tsuno、Kosuke Kondo、Kunio Sugiyama

  DOI：10.1002/jhet.5570430104

  日期：2006.1

  The α-oxo ketenes 6 which are generated by the pyrolysis of the 2-aryl-substituted 1,5,7-trioxaspiro[2.5]octane-4,8-diones 1, were reacted with Schiff bases 2 to give spiro compounds constructed between the β-lactam and 1,3-dioxolan-4-one; i.e., the 2,3,6-triaryl-2-aza-5,7-dioxaspiro[3.4]octane-1,8-diones 3 and 4. Hydrogenation of the mixture of 3a and 4a in the presence of catalytic amount of Pd-C

  通过2-芳基取代的1,5,7-三氧杂螺[2.5]辛烷-4​​,8-​​二酮1的热解反应生成的α-氧代乙烯酮6与席夫碱2反应，得到在以下基团之间构筑的螺环化合物β-内酰胺和1,3-二氧戊环-4-酮；即2,3,6-三芳基-2-氮杂-5,7-二氧杂螺[3.4]辛烷-1,8-二酮3和4。在催化量的Pd-C存在下3a和4a混合物的氢化反应生成反式-2-苄氧基-1,4-二苯基-β-内酰胺-3-羧酸9。