1-Acetylspiro-2'(1')-one | 142634-90-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1-Acetylspiro-2'(1')-one
• 英文别名: 1-acetylspiroindol>-2'(1'H)-one；N-acetyl-spiro-cyclopentyl-1,3’-indol-2’-one；1'-acetyl-spiro[cyclopentane-1,3'-indolin]-2'-one；1'-Acetyl-spiro[cyclopentan-1,3'-indolin]-2'-on；1'-Acetylspiro[cyclopentane-1,3'-indole]-2'-one
• CAS: 142634-90-0
• 化学式: C₁₄H₁₅NO₂
• 分子量: 229.279
• InChiKey: NLDJMJWGLANOSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 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：

  1-Acetylspiro-2'(1')-one 在 三乙基硅烷 、 sodium hydroxide 、 三氯化铝 、 sodium carbonate 、 三氟乙酸 、 sodium iodide 作用下， 以 甲醇 、 二硫化碳 为溶剂， 反应 72.5h， 生成 5'-{2-[4-(1,2-benzoisothiazol-3-yl)piperazinyl]ethyl}-3,3-spirocyclopentane-1,3-dihydro-2(1H)-indol-2-one
  参考文献：
  名称：

  3-Benzisothiazolylpiperazine Derivatives as Potential Atypical Antipsychotic Agents

  摘要：

  A series of substituted phenethyl derivatives of 3-benzisothiazolylpiperazine incorporating potent D-2 and 5-HT2A antagonist activity was investigated as an approach to a novel atypical antipsychotic agent. The in vitro profile of 8e from this series is a combination of D-2 receptor affinity comparable to the typical antipsychotic agent haloperidol and a 5-HT2A/D-2 ratio comparable to the atypical agent clozapine. In vivo 8e possesses activity consistent with an efficacious antipsychotic agent with less tendency to induce extrapyramidal side effects in man.

  DOI：

  10.1021/jm950625l
• 作为产物：
  描述：

  9-乙酰基-2,3,4,9-四氢-1H-咔唑 在 Oxone 、 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 生成 1-Acetylspiro-2'(1')-one
  参考文献：
  名称：

  N-酰基四氢-β-咔啉在氧酮/丙酮水溶液中的氧化重排反应合成吡咯并吡咯烷二酮

  摘要：

  使用原位生成的二甲基二环氧乙烷，通过N-乙酰基1,2,3,4-四氢-β-咔啉（THBC）的氧化重排制备螺-吡咯烷基-2-氧吲哚。N乙酰基THBC底物通过L-色氨酸甲酯的Pictet-Spengler和酰基-Pictet-Spengler反应，然后进行N-乙酰化而获得。评估了氧化重排的立体选择性，并使用2D核磁共振（NMR）确定了羟吲哚产物相对于L-色氨酸的立体化学。密度泛函理论计算与吲哚双键的面选择性，受底物控制的环氧化作用一致。计算表明，所得的环氧化物将通过协调的开环/开环过程在室温下容易地重排，得到3-取代的2-氧吲哚。

  DOI：

  10.21577/0103-5053.20180149

文献信息

• Oxidation of indoles by singlet oxygen and dimethyldioxirane: Isolation of indole dioxetanes and epoxides by stabilization through nitrogen acylation
  作者：Waldemar Adam、Michael Ahrweiler、Markus Sauter、Bernd Schmiedeskamp

  DOI：10.1016/s0040-4039(00)73964-5

  日期：1993.8

  through N-acylation allowed the isolation of the labile indole dioxetanes 2, which were transformed by dimethyl sulfide deoxygenation to the corresponding indole epoxides 5; the latter were also independently prepared by dimethyldioxirane oxidation.

  通过N-酰化作用的稳定作用可以分离出不稳定的吲哚二氧杂环丁烷2，其通过二甲基硫醚的脱氧作用转化为相应的吲哚环氧化物5。后者也通过二甲基二环氧乙烷氧化独立制备。
• Investigation of the selective reduction of isatin derivatives. Synthesis of α-hydroxyacetophenone derivatives and ethyl spiro-3,3-(ethylenedioxy)-2-hydroxyindoline carboxylates
  作者：Simon J. Garden、Marilza B. Côrrea、Angelo C. Pinto

  DOI：10.1016/j.tetlet.2003.08.058

  日期：2003.10

  The product from the reduction of ethyl spiro-3,3-(ethylenedioxy)-2-oxindole carboxylates (1) using borohydride salts has been found to be dependant upon both solvent and metal ion. With polar solvents and lithium bromide/sodium borohydride, spiro-3,3-(ethylenedioxy)-2-hydroxyindole carboxylates (2) are obtained in high yields whilst [2-(2-hydroxymethyl-[1,3]dioxolan-2-yl)-phenyl]-carbamic acid ethyl

  已经发现使用硼氢化物盐还原乙基螺-3，3-（亚乙基二氧基）-2-氧吲哚羧酸盐（1）的产物既依赖于溶剂又依赖于金属离子。使用极性溶剂和溴化锂/硼氢化钠，可以高产率获得螺-3,3-（亚乙二氧基）-2-羟基吲哚羧酸酯（2），而[2-（2-羟甲基-[1,3]二氧戊环-2-）使用硼氢化钠在极性较小的溶剂中获得[ （yl）-苯基]-氨基甲酸乙酯（3）。
• Oxidation of N-Acylindoles by Dimethyldioxirane and Singlet Oxygen: Substituent Effects on Thermally Persistent Indole Epoxides and Dioxetanes
  作者：Waldemar Adam、Michael Ahrweiler、Karl Peters、Bernd Schmiedeskamp

  DOI：10.1021/jo00089a016

  日期：1994.5

  Photooxygenation of the N-acylindoles 1a-d afforded the labile indole dioxetanes 2 and the relatively stable allylic hydroperoxides 3. The dioxetanes 2a,c,d were sufficiently stable for isolation and spectral characterization. Additionally, they were characterized by chemical transformations, namely reduction to the indole epoxides 5 by dimethyl sulfide, acid-catalyzed rearrangement to allylic hydroperoxides 3c,d, and thermolysis to the cleavage products 4. Oxidation of the N-acylindoles I with dimethyldioxirane afforded the epoxides 5, which were characterized on the basis of their spectral data and chemical transformations to the 2-indolinones 6 and 2-methyleneindoline 7. These decomposition products (except 7e) were fully characterized. The stability of the epoxides 5 depended on the substitution type, i.e., the carbazole epoxide 5c decomposed already at temperatures above ca. -50 degrees C, whereas the cyclopentindole epoxide 5b was stable at 20 degrees C for days. The latter was unequivocally characterized by X-ray analysis.
• Perkin; Plant, Journal of the Chemical Society, 1923, vol. 123, p. 680,688
  作者：Perkin、Plant

  DOI：——

  日期：——
• Adam, Waldemar; Ahrweiler, Michael; Paulini, Klaus, Chemische Berichte, 1992, vol. 125, # 12, p. 2719 - 2722
  作者：Adam, Waldemar、Ahrweiler, Michael、Paulini, Klaus、Reissig, Hans-Ulrich、Voerckel, Volkmar

  DOI：——

  日期：——