帕利哌酮杂质12 | 53855-26-8

• 物质功能分类: 有机原料 - 酮类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 中文名称: 帕利哌酮杂质12
• 英文名称: 2-formyl-γ-butyrolactone
• 英文别名: (2-hydroxy-ethyl)-malonaldehydic acid-lactone；(2-Hydroxy-aethyl)-malonaldehydsaeure-lacton；2-formylbutyrolactone；α-Aldehydo-γ-butyrolacton；2-Oxotetrahydrofuran-3-carbaldehyde；2-oxooxolane-3-carbaldehyde
• CAS: 53855-26-8
• 化学式: C₅H₆O₃
• 分子量: 114.101
• InChiKey: YVWPGWMYXNVKQV-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C
• 沸点：
  93-100 °C(Press: 3 Torr)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  帕利哌酮杂质12 在 乙醇 、 镍 作用下， 100.0 ℃ 、9.81 MPa 条件下， 生成 α-hydroxymethyl-γ-butyrolactone
  参考文献：
  名称：

  Lactone derivatives and method of making

  摘要：

  公开号：

  US02624723A1
• 作为产物：
  描述：

  γ-丁内酯 、 甲酸乙酯 在 molecular sieve 、 TiCl₂(OTf)2 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以52%的产率得到帕利哌酮杂质12
  参考文献：
  名称：

  二氯-双（三氟甲烷磺酸）钛（IV）作为克莱森酯缩合反应的有效促进剂

  摘要：

  酯官能之间的分子间和分子内缩合（Claisen 和 Dieckmann 缩合）已通过在温和条件下结合使用二氯双（三氟甲磺酸）钛 (IV) 和叔胺来实现。

  DOI：

  10.1246/cl.1984.1867

文献信息

• Preparation of 1,1-disubstituted ethylene compounds
  申请人：BASF Aktiengesellschaft

  公开号：US04997955A1

  公开（公告）日：1991-03-05

  1,1-disubstituted ethylene compounds of the general formula I ##STR1## where Z is COOR.sup.2, CN or COR.sup.3, R.sup.1 is an aliphatic, cycloalophatic, araliphatic, aromatic or heterocyclic radical which may be further substituted by functional groups which are inert under the reaction conditions, R.sup.2 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms and R.sup.3 is an aliphatic, cycloaliphatic or araliphatic radical of 1 to 15 carbon atoms which may be substituted by groups which are inert under the reaction conditions, and R.sup.1 together with R.sup.2 or R.sup.1 together with R.sup.3 may furthermore form an alkylene chain of 2 to 10 carbon atoms which may be substituted by groups which are inert under the reaction conditions, are prepared from a formyl compound of the general formula II ##STR2## where Z, R.sup.1, R.sup.2 and R.sup.3 have the above meanings, by a process in which the reaction is carried out in the presence of formaldehyde or paraformaldehyde and (a) a C.sub.1 -C.sub.12 -alkanol or (b) a mixture of a C.sub.1 -C.sub.12 -alkanol and water or (c) with water in the presence of a secondary amine and a protic acid at from 0.degree. to 200.degree. C.

  通式I的1,1-二取代乙烯化合物如下：其中Z为COOR.sup.2、CN或COR.sup.3，R.sup.1为脂肪、环脂肪、芳基脂肪、芳香族或杂环基团，可能进一步被在反应条件下惰性的官能团取代，R.sup.2为1至15个碳原子的脂肪、环脂肪或芳基脂肪基团，R.sup.3为1至15个碳原子的脂肪、环脂肪或芳基脂肪基团，可能被在反应条件下惰性的基团取代，且R.sup.1与R.sup.2或R.sup.1与R.sup.3还可以形成2至10个碳原子的烷基链，该链可能被在反应条件下惰性的基团取代，这些化合物是从通式II的甲醛化合物制备而来：其中Z、R.sup.1、R.sup.2和R.sup.3具有上述含义，通过在甲醛或多聚甲醛的存在下进行反应，以及(a)C.sub.1-C.sub.12-醇或(b)C.sub.1-C.sub.12-醇和水的混合物或(c)在二级胺和具有质子的酸存在下与水在0°C至200°C范围内进行反应的方法。
• The Selective Claisen and Dieckmann Ester Condensations Promoted by Dichlorobis(trifluoromethanesulfonato)titanium(IV)
  作者：Yoo Tanabe

  DOI：10.1246/bcsj.62.1917

  日期：1989.6

  Inter and intramolecular condensations (the Claisen and the Dieckmann condensations) between ester functions have been performed by the combined use of dichlorobis(trifluoromethanesulfonato)titanium(IV) (= dichlorobis(triflato)titanium(IV)) and tertiary amine under mild reaction conditions. These results led to the development of the selective (crossed) Claisen and Dieckmann ester condensation between

  酯官能之间的分子间和分子内缩合（Claisen 和 Dieckmann 缩合）已通过在温和的反应条件下联合使用二氯双（三氟甲磺酸根）钛（IV）（= 二氯双（三氟甲磺酸根）钛（IV））和叔胺进行。这些结果导致甲氧基甲酯和甲酯之间的选择性（交叉）克莱森和迪克曼酯缩合的发展，因为二氯双（三氟甲磺酸根）钛（IV）有助于控制反应方向。
• Korte; Machleidt, Chemische Berichte, 1955, vol. 88, p. 1676,1679
  作者：Korte、Machleidt

  DOI：——

  日期：——
• Korte; Buechel, Chemische Berichte, 1959, vol. 92, p. 877,881
  作者：Korte、Buechel

  DOI：——

  日期：——
• Bifuctional Amino-Squaramides Catalyzed Asymmetric Spiroannulation Cascades with Aliphatic β,γ-Unsaturated α-Keto Esters: Controlling an Aldehyde Enolate
  作者：Xiaoqin Wang、Weijun Yao、Zhihui Yao、Cheng Ma

  DOI：10.1021/jo202633c

  日期：2012.3.16

  A quinidine-derived squaramide Ib catalyzed cyclization reaction of beta-oxo aldehydes 1 and aliphatic or aromatic beta,gamma-unsaturated alpha-keto ester 2 is described. Using cyclic aldehyde substrates, this procedure provided a promising approach to a variety of spiro-3,4-dihydropyrans bearing three continuous quaternary and tertiary stereocenters in moderate to good yield with high stereoselectivities. Substituents on the nitrogen atoms of the squaramide moiety of the catalyst proved crucial to the reaction outcome. The stereochemistry of the three newly formed chiral centers (trans-selective) of the major product indicates a Micheal addition/hemiacetalization domino sequence for the present annulations.