2-(3-benzoylpropyl)-2-phenyl-1,3-dioxolane | 133549-24-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-benzoylpropyl)-2-phenyl-1,3-dioxolane
• 英文别名: 1-Phenyl-4-(2-phenyl-1,3-dioxolan-2-yl)butan-1-one
• CAS: 133549-24-3
• 化学式: C₁₉H₂₀O₃
• 分子量: 296.366
• InChiKey: RJNRIKDAFAQJPX-UHFFFAOYSA-N

物化性质

• 沸点：
  434.3±30.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-benzoylpropyl)-2-phenyl-1,3-dioxolane 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以98%的产率得到1,5-二苯基-1,5-戊二酮
  参考文献：
  名称：

  Masked lithium bishomoenolates: useful intermediates in organic synthesis

  摘要：

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.

  DOI：

  10.1021/jo00012a012
• 作为产物：
  描述：

  2-(3-chloropropyl)-2-phenyl-[1,3]dioxolane 、 苯甲腈 生成 2-(3-benzoylpropyl)-2-phenyl-1,3-dioxolane
  参考文献：
  名称：

  Masked lithium bishomoenolates: useful intermediates in organic synthesis

  摘要：

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.

  DOI：

  10.1021/jo00012a012

文献信息

• CYCLIC AMINO COMPOUNDS FOR USE IN THE TREATMENT OF CARDIAC DISORDERS
  申请人：Universitetet I Oslo

  公开号：US20150141456A1

  公开（公告）日：2015-05-21

  The present invention relates to tertiary amines of formula (I) for use in therapy, particularly for use in treating cardiovascular disorders. The compounds have been found to regulate phospholamban phosphorylation by interfering with the A-kinase anchor protein 18delta (AKAP18δ) binding to the PKA substrate phospholamban. The compounds share a tri(alkylaryl/alkylheteroaryl) amine structure.

  本发明涉及用于治疗的式(I)的三级胺，特别是用于治疗心血管疾病。已发现这些化合物通过干扰A-激酶锚定蛋白18δ（AKAP18δ）与PKA底物磷蛋白的结合来调节磷蛋白激酶的磷酸化。这些化合物共享三（烷基芳基/烷基杂芳基）胺结构。
• Mansri, Ali; Casals, Pierre-Francois; Fan, Bo Tao, Bulletin de la Societe Chimique de France, 1994, vol. 131, # 3, p. 247 - 252
  作者：Mansri, Ali、Casals, Pierre-Francois、Fan, Bo Tao、Lapluye, Gerard

  DOI：——

  日期：——
• RAMON, DIEGO J.;YUS, MIGUEL, J. ORG. CHEM., 56,(1991) N2, C. 3825-3831
  作者：RAMON, DIEGO J.、YUS, MIGUEL

  DOI：——

  日期：——
• US9585880B2
  申请人：——

  公开号：US9585880B2

  公开（公告）日：2017-03-07