8-benzyl-8-azaspiro[4.5]decane-7,9-dione | 77261-38-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 8-benzyl-8-azaspiro[4.5]decane-7,9-dione
• CAS: 77261-38-2
• 化学式: C₁₆H₁₉NO₂
• mdl: MFCD03648435
• 分子量: 257.332
• InChiKey: SJCIEKUZELQGLB-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  463.6±24.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-benzyl-8-azaspiro[4.5]decane-7,9-dione 在 potassium tert-butylate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 48.75h， 生成 allyl 8-benzyl-6-(difluoromethyl)-7,9-dioxo-8-azaspiro[4.5]decane-6-carboxylate
  参考文献：
  名称：

  A Unified Strategy for the Synthesis of Difluoromethyl- and Vinylfluoride-Containing Scaffolds

  摘要：

  Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.

  DOI：

  10.1021/acs.orglett.9b02887
• 作为产物：
  描述：

  7,9-二氧代-8-氮杂螺[4.5]癸烷-6,10-二甲腈 在 氯化亚砜 、 硫酸 、 乙酸酐 、 sodium hydride 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 mineral oil 为溶剂， 反应 6.0h， 生成 8-benzyl-8-azaspiro[4.5]decane-7,9-dione
  参考文献：
  名称：

  Antiproliferative and antibacterial activity of some glutarimide derivatives

  摘要：

  Antiproliferative and antibacterial activities of nine glutarimide derivatives (1-9) were reported. Cytotoxicity of compounds was tested toward three human cancer cell lines, HeLa, K562 and MDA-MB-453 by MTT assay. Compound 7 (2-benzyl-2-azaspiro[5.11] heptadecane-1,3,7-trione), containing 12-membered ketone ring, was found to be the most potent toward all tested cell lines (IC50 = 9-27 mu M). Preliminary screening of antibacterial activity by a disk diffusion method showed that Gram-positive bacteria were more susceptible to the tested compounds than Gram-negative bacteria. Minimum inhibitory concentration (MIC) determined by a broth microdilution method confirmed that compounds 1, 2, 4, 6-8 and 9 inhibited the growth of all tested Gram-positive and some of the Gram-negative bacteria. The best antibacterial potential was achieved with compound 9 (ethyl 4-(1-benzyl-2,6-dioxopiperidin-3-yl) butanoate) against Bacillus cereus (MIC 0.625 mg/mL; 1.97 x 10(-3) mol/L). Distinction between more and less active/inactive compounds was assessed from the pharmacophoric patterns obtained by molecular interaction fields.

  DOI：

  10.3109/14756366.2015.1070844

文献信息

• Synthesis and Evaluation of (Piperidinomethylene)bis(phosphonic acid) Derivatives as Anti-osteoporosis Agents.
  作者：Mitsuo MIMURA、Mitsuo HAYASHIDA、Kiyoshi NOMIYAMA、Satoru IKEGAMI、Yasuhito IIDA、Makoto TAMURA、Yoshiyuki HIYAMA、Yoshitaka OHISHI

  DOI：10.1248/cpb.41.1971

  日期：——

  Some (piperidinomethylene)bis(phosphonic acid) derivatives were prepared and their activity to inhibit a rise in serum calcium induced by parathyroid hormone in thyroparathyroidectomised rats was evaluated. Several (4-alkylidene-, 4,4-dialkyl-, or 4-alkyl-4-halopiperidinomethylene)bis(phosphonic acid) derivatives showed considerable inhibitory activity. But compounds having aromatic and polar substituents

  制备了一些（哌啶子基亚甲基）双（膦酸）衍生物，并评估了它们抑制甲状旁腺切除的大鼠的甲状旁腺激素诱导的血清钙升高的活性。几种（4-亚烷基-，4,4-二烷基-或4-烷基-4-卤代哌啶亚基）双（膦酸）衍生物表现出相当大的抑制活性。但是在哌啶环上具有芳族和极性取代基如叠氮基，羟基，氨基和酰胺基的化合物通常是无活性的。在这项研究中，两种4-亚烷基化合物（8a和8b）和4,4-环二烷基化合物（61）在静脉内或经口给药时均显示出强大的活性。
• Cu(OTf)₂ catalyzed Ugi-type reaction of <i>N</i>,<i>O</i>-acetals with isocyanides for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides
  作者：Zhuo-Ya Mao、Xiao-Di Nie、Yi-Man Feng、Chang-Mei Si、Bang-Guo Wei、Guo-Qiang Lin

  DOI：10.1039/d1cc03113a

  日期：——

  The Cu(OTf)2 catalyzed Ugi-type reactions of N,O-acetals with isocyanides have been described for the synthesis of pyrrolidinyl and piperidinyl 2-carboxamides. 4-Hydroxy-5-substituted-prolinamides can be obtained in high diastereoselectivities (2,4-cis/trans > 19 : 1) and a stereoselective model was proposed for 2,4-cis selectivity. Moreover, 4-F-VH 032, a novel analog of the VHL ligand, was conveniently

  已经描述了用于合成吡咯烷基和哌啶基 2-甲酰胺的 Cu(OTf) 2催化的N，O-缩醛与异氰化物的Ugi 型反应。4-羟基-5-取代的脯氨酰胺可以以高非对映选择性（2,4-顺式/反式> 19:1）获得，并且提出了2,4-顺式选择性的立体选择性模型。此外，4-F-VH 032，一种新型的 VHL 配体类似物，可以通过使用本方法方便地获得。
• Zeid; El-Telbany; Khalifa, Pharmazie, 1980, vol. 35, # 11, p. 669 - 671
  作者：Zeid、El-Telbany、Khalifa

  DOI：——

  日期：——
• ZEID M. G.; EL-TELBANY F. A.; KHALIFA M., PHARMAZIE, 1980, 35, NO 11, 669-671
  作者：ZEID M. G.、 EL-TELBANY F. A.、 KHALIFA M.

  DOI：——

  日期：——