4-(neopentyloxycarbonyl)cyclohexanone | 476373-81-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(neopentyloxycarbonyl)cyclohexanone
• 英文别名: neopentyl 4-oxocyclohexanecarboxylate；2,2-Dimethylpropyl 4-oxocyclohexane-1-carboxylate
• CAS: 476373-81-6
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: WFGQZMIKWDRTQO-UHFFFAOYSA-N

物化性质

• 沸点：
  289.0±33.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(neopentyloxycarbonyl)cyclohexanone 在 palladium on activated charcoal 氢气 、 N,N-二甲基甲酰胺二新戊基乙缩醛 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 生成 4-(3,3-Dimethyl-1,5-dioxa-spiro[5.5]undec-9-yl)-cyclohexanecarboxylic acid 2,2-dimethyl-propyl ester
  参考文献：
  名称：

  Oligo(Cyclohexylidene)s and Oligo(Cyclohexyl)s as Bridges for Photoinduced Intramolecular Charge Separation and Recombination

  摘要：

  A series of semirigid donor-bridge-acceptor (D-B-A) molecules was synthesized to study the effect of the position and number of nonconjugated olefinic bonds in the bridge on the photoinduced charge-separation and charge-recombination kinetics. The molecules consist of a phenylpiperidine electron donor, an oligo(cyclohexylidene) or oligo(cyclohexyl) bridge, and a dicyanovinyl acceptor. Partly saturated ter(cyclohexylidene) bridges were used as well. The edge-to-edge donor-acceptor separation of the compounds under study varies between 2.89 and 15.4 Angstrom. The replacement of a C-C single bond by an olefinic bond increases the rate of charge separation with a factor of 3.0 +/- 0.8 per replaced bond. For all D-B-A compounds the extended fully charge-separated state folds to a compact charge-transfer (CCT) conformer. The rate of charge recombination (CR) of the CCT state increases with solvent polarity for those compounds having an olefinic bond located three sigma bonds from the acceptor. Thus, while in cyclohexane the CR rate is equal for all compounds, in benzene the CR rate in compounds with an olefinic bond near the acceptor is 10 times larger than in compounds with a single bond instead. It is believed that a (virtual) charge-transfer state involving the radical cation of the olefinic bond and the radical anion of the acceptor (D-B.+-A(.-)) is responsible for the enhanced CR process.

  DOI：

  10.1021/jp0271716
• 作为产物：
  描述：

  triethyl 4-oxocyclohexane-1,1,3-tricarboxylate 在 盐酸 作用下， 生成 4-(neopentyloxycarbonyl)cyclohexanone
  参考文献：
  名称：

  Oligo(Cyclohexylidene)s and Oligo(Cyclohexyl)s as Bridges for Photoinduced Intramolecular Charge Separation and Recombination

  摘要：

  A series of semirigid donor-bridge-acceptor (D-B-A) molecules was synthesized to study the effect of the position and number of nonconjugated olefinic bonds in the bridge on the photoinduced charge-separation and charge-recombination kinetics. The molecules consist of a phenylpiperidine electron donor, an oligo(cyclohexylidene) or oligo(cyclohexyl) bridge, and a dicyanovinyl acceptor. Partly saturated ter(cyclohexylidene) bridges were used as well. The edge-to-edge donor-acceptor separation of the compounds under study varies between 2.89 and 15.4 Angstrom. The replacement of a C-C single bond by an olefinic bond increases the rate of charge separation with a factor of 3.0 +/- 0.8 per replaced bond. For all D-B-A compounds the extended fully charge-separated state folds to a compact charge-transfer (CCT) conformer. The rate of charge recombination (CR) of the CCT state increases with solvent polarity for those compounds having an olefinic bond located three sigma bonds from the acceptor. Thus, while in cyclohexane the CR rate is equal for all compounds, in benzene the CR rate in compounds with an olefinic bond near the acceptor is 10 times larger than in compounds with a single bond instead. It is believed that a (virtual) charge-transfer state involving the radical cation of the olefinic bond and the radical anion of the acceptor (D-B.+-A(.-)) is responsible for the enhanced CR process.

  DOI：

  10.1021/jp0271716

文献信息

• Spiro and dispiro 1,2,4-trioxolane antimalarials
  申请人：Medicines for Malaria Venture MMV International Centre Cointrin

  公开号：US06486199B1

  公开（公告）日：2002-11-26

  A means and method for treating malaria using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl or spiropiperidyl ring on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably functionalized or substituted at the 4-position or a spiropiperidyl ring that is functionalized or substituted at the nitrogen atom. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  描述了一种利用螺环或二螺环1,2,4-三噁烷治疗疟疾的方法和手段。首选的1,2,4-三噁烷包括在三噁烷基团的一侧具有螺环戊烷基团，并在三噁烷基团的另一侧具有螺环环己基或螺环哌啶基团，其中螺环环己基环在4-位功能化或取代，或者螺环哌啶基团在氮原子处功能化或取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有强效作用。
• Synthesis of Tetrasubstituted Ozonides by the Griesbaum Coozonolysis Reaction:  Diastereoselectivity and Functional Group Transformations by Post-Ozonolysis Reactions
  作者：Yuanqing Tang、Yuxiang Dong、Jean M. Karle、Charles A. DiTusa、Jonathan L. Vennerstrom

  DOI：10.1021/jo040171c

  日期：2004.9.1

  coozonolysis reaction with O-methyl 2-adamantanone oxime and 4-substituted cyclohexanones reveals that the major tetrasubstituted ozonide isomers possess cis configurations, suggesting a preferred axial attack of the carbonyl oxide on the cyclohexanone dipolarophiles. It is evident that these tetrasubstituted ozonides are quite stable to triphenylphosphine, borohydrides, hydrazine, alkyllithiums, Grignard

  与O-甲基2-金刚烷酮肟和4-取代的环己酮的格里斯鲍姆共渗分解反应的非对映选择性表明，主要的四取代的臭氧化物异构体具有顺式构型，表明羰基氧化物优选对环己酮双极性亲和剂的轴向攻击。显然，这些四取代的臭氧化物对三苯基膦，硼氢化物，肼，烷基锂，格利雅试剂，硫醇盐和KOH水溶液非常稳定，如胺，醇，酸，酯，醚，硫化物，砜和杂环化合物的合成所示。通过各种臭氧分解后的转化功能化了臭氧化物。
• [EN] 1,2,4-TRIOXOLANE ANTIMALARIALS<br/>[FR] ANTIPALUDIQUES A BASE DE 1,2,4-TRIOXOLANE
  申请人：MEDICINES MALARIA VENTURE MMV

  公开号：WO2003000676A1

  公开（公告）日：2003-01-03

  A means and method for treating malaria, schistosomiasis, and cancer using a spiro or dispiro 1,2,4-trioxolane is described. The preferred 1,2,4-trioxolanes include a spiroadamantane group on one side of the trioxolane group, and a spirocyclohexyl on the other side of the trioxolane group, whereby the spirocyclohexyl ring is preferably substituted at the 4-position. In comparison to artemisinin semisynthetic derivatives, the compounds of this invention are structurally simple, easy to synthesize, non-toxic, and potent against malarial parasites.

  本发明涉及使用螺环或双螺环1,2,4-三噁烷治疗疟疾、血吸虫病和癌症的方法和手段。首选的1,2,4-三噁烷包括一个螺环戊烷基团位于三噁烷基团的一侧，以及一个螺环己基位于三噁烷基团的另一侧，其中螺环己环在4位处优选被取代。与青蒿素半合成衍生物相比，本发明的化合物结构简单，易于合成，无毒，并且对疟原虫具有很强的杀灭作用。
• 1,2,4-TRIOXOLANE ANTIMALARIALS
  申请人：Medicines for Malaria Venture

  公开号：EP1414813B1

  公开（公告）日：2006-09-13
• US6486199B1
  申请人：——

  公开号：US6486199B1

  公开（公告）日：2002-11-26