3-[2-Cyanoethyl(propan-2-yl)amino]propanenitrile | 27850-34-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[2-Cyanoethyl(propan-2-yl)amino]propanenitrile
• CAS: 27850-34-6
• 化学式: C₉H₁₅N₃
• mdl: MFCD16041186
• 分子量: 165.238
• InChiKey: PUAMREYMBHDAJT-UHFFFAOYSA-N

物化性质

• 沸点：
  121 °C(Press: 0.5 Torr)
• 密度：
  0.963±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.777
• 拓扑面积：
  50.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[2-Cyanoethyl(propan-2-yl)amino]propanenitrile 在 三正丙胺 、 sodium ethanolate 、 sodium hexamethyldisilazane 作用下， 以 乙醚 、 乙醇 、 乙二醇甲醚 为溶剂， 反应 18.0h， 生成 4-(2-Fluorophenyl)-12-propan-2-yl-3,5,6,8,12-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4-trien-7-one
  参考文献：
  名称：

  Anxiolytic properties of certain annelated [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones

  摘要：

  Modification of the benzodiazepine (BZ) receptor binding template 2-aryl[1,2,4]triazolo[1,5-c]quinazolin-5(6H)-one by replacement of the annelated benzene ring with various alicyclic and heterocyclic moieties led to novel structures with potent BZ receptor binding affinity. High affinity was found in some cycloalkyl-annelated [1,2,4]triazolo-[1,5-c]pyrimidin-5(6H)-ones and in some 7,8,9,10-tetrahydropyrido[3,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones, in which the degree of activity was strongly dependent on the N-substituent in the 9-position. Nine compounds with BZ receptor IC50 binding affinity values equal or superior to diazepam were evaluated in secondary screening. One of these, 9-benzyl-2-phenyl-7,8,9,10-tetrahydropyrido[3,4-e]?? [1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one, showed good activity in rats as a potential anxiolytic agent without sedative liability. However, it increased the rotorod deficit produced by ethanol at anxiolytic doses, an indication of alcohol interaction. Thus, none of the compounds showed an advantage over CGS 9896 (Yokoyama et al. J. Med. Chem. 1982, 25, 337-339), which is free of sedative and alcohol interaction potential as measured by the test procedures described.

  DOI：

  10.1021/jm00113a032
• 作为产物：
  描述：

  异丙胺 、 丙烯腈 在 [{kp,kc,kp-2,6-(i-Pr₂PO)2C₆H₃}Ni(NCMe)][OSO₂CF₃] 、 三乙胺 作用下， 以 氘代苯 为溶剂， 以100%的产率得到3-[2-Cyanoethyl(propan-2-yl)amino]propanenitrile
  参考文献：
  名称：

  胺和酚的加成丙烯腈由POCOP型钳形催化衍生物复杂[{κ P，κ Ç，κ P -2,6-（我-Pr 2 PO）2 C ^ 6 ħ 3 }的Ni（NCMe）] [ OSO 2 CF 3 ]

  摘要：

  钳型配合物[{κ P，κ Ç，κ P -2,6-（我-Pr 2 PO）2 C ^ 6 ħ 3 }的Ni（NCMe）] [OSO 2 CF 3 ]（1）可以用作亲核试剂向活性烯烃的区域选择性，反马尔科夫尼科夫加成的前催化剂。脂肪胺在丙烯腈，甲基丙烯腈和巴豆腈中的催化加成反应在室温下进行，并由于形成了C–N键而产生定量的产物收率。另一方面，芳族胺或醇对甲基丙烯腈和巴豆腈是完全惰性的，对丙烯腈的反应性小得多，需要添加碱，加热和延长的反应时间才能获得良好的收率。1的催化反应性据认为是由于配位乙腈的取代不稳定性所致，该取代基使得烯烃底物中腈部分具有竞争性配位；这种结合增强了CC部分的亲电子性，使它们更易于受到亲核试剂的攻击。在某些情况下，RCN→Ni结合会导致双键异构化/迁移（烯丙基氰化物）或亲核体在腈部分（肉桂腈和4-氰基苯乙烯）的侵蚀。吗啉与1在60°C下反应导致形成formation衍生物2，该X衍生物2已通过X射线晶体学表征。

  DOI：

  10.1016/j.molcata.2010.11.010

文献信息

• 2-Substituted-e-fused-[1,2,4,]triazolo-[1,5-c]pyrimidines pharmaceutical compositions and uses thereof
  申请人：CIBA-GEIGY AG

  公开号：EP0217748A2

  公开（公告）日：1987-04-08

  Compounds of the formulae la, Ib and Ic wherein X is 0, S, NH or NR; R is alkyl, alkenyl, alkynyl, cycloalkyl, aromatic-ring-alkyl all of which may be optionally interrupted by a herero atom: OH; an aromatic ring; or the group -C(=NH)-NH2; R1 is optionally substituted and selected from a carboxylic aromatic and a heterocyclic group which heterocyclic group is aromatic, partially saturated or fully saturated, the optional substituent of R1 being halogen, alkyl, haloalkyl, OH, alkoxy, hydroxyalkyl, amino, mono- or di-alkylamino, carbalkoxy, carbamoyl and alkylcarbamoyl; R2 is H, alkyl, hydroxy-C2-C4-alkyl, alkenyl, arylalkyl, or arylalkenyl; A is a bivalent bridging group containing chain atoms selected from C, 0, N and S thus forming together with the two adjacent carbon atoms to which the chain is attached a mono- or bicyclic carbocyclic or heterocyclic group with the proviso that a monocyclic group formed by A is saturated or partially saturated and that the ring moiety adjacent to the triazolopyrimidine structure in a bicyclic, carbocyclic or heterocyclic group is other than carbocyclic aromatic, and A is optionally substituted by substituents from the group consisting of alkyl. alkoxy, hydroxy, halogen, haloalkyl, N02, NH2, lower alkylthio. lower alkylsulfonyl, lower alkylsulfinyl, aryl-lower alkyl, amido. carbamoyl, carbalkoxy or aroyl; and pharmaceutically acceptable salts thereof.

  式 la、Ib 和 Ic 的化合物 其中 X 是 0、S、NH 或 NR； R 是烷基、烯基、炔基、环烷基、芳环烷基，所有这些烷基可任选被一个herero 原子打断：OH；芳香环；或基团-C(=NH)-NH2； R1 被任选取代，选自羧基芳香基和杂环基（杂环基为芳香基、部分饱和或完全饱和），R1 的任选取代基为卤素、烷基、卤代烷基、OH、烷氧基、羟基烷基、氨基、单或双烷基氨基、碳烷氧基、氨基甲酰基和烷基氨基甲酰基； R2 是 H、烷基、羟基-C2-C4-烷基、烯基、芳基烷基或芳基烯基； A 是含有选自 C、0、N 和 S 的链原子的二价桥基，从而与链所连接的两个相邻碳原子一起形成单环或双环碳环或杂环基团，但 A 所形成的单环基团必须是饱和或部分饱和的，并且与三唑并嘧啶结构相邻的环分子必须是双环的、由 A 形成的单环基团是饱和或部分饱和的，且在双环、碳环或杂环基团中与三唑并嘧啶结构相邻的环分子是碳环芳香族以外的，且 A 可选择被由以下组成的取代基取代烷氧基、羟基、卤素、卤代烷基、N02、NH2、低级烷硫基、低级烷基磺酰基、低级烷基亚磺酰基、芳基-低级烷基、氨基、氨基甲酰基、碳烷氧基或芳基；及其药学上可接受的盐类。
• 2-Substituted-e-fused-[1,2,4]-triazolo[1,5-c] pyrimidines, pharmaceutical compositions, and uses thereof
  申请人：CIBA-GEIGY AG

  公开号：EP0263071A1

  公开（公告）日：1988-04-06

  Compounds of the formula wherein R1 is optionally substituted phenyl, pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, or ribofuranosyl; X is oxygen, NR, or sulfur: R is hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and ring A is a) an optionally substituted 5-8 membered monocycloalken-1,2-diyl; b) an optionally substituted carbob- icyclic ring of the formula. wherein n and m are each independently one or two; or c) an optionally substituted 5-6 membered heterocycle having one or two heteroatoms, the atoms of which are selected from carbon, oxygen, nitrogen, and sulfur. Also disclosed are tautomers of the above and pharmaceutically acceptable salts; compositions thereof; and methods of using the compounds, tautomer, or salts.

  式中的化合物 其中 R1 是任选取代的苯基、吡啶基、噻吩基、呋喃基、吡咯基、噻唑基或呋喃核糖基；X 是氧、NR 或硫：R 是氢、低级烷基、低级烯基或低级炔基；以及环 A 是 a）任选取代的 5-8 位单环烯-1,2-二基；b）式中任选取代的碳冰环。 其中 n 和 m 各自独立地为一个或两个；或 c) 具有一个或两个杂原子的任选取代的 5-6 分子杂环，这些杂原子选自碳、氧、氮和硫。还公开了上述化合物的同系物和药学上可接受的盐；其组合物；以及使用这些化合物、同系物或盐的方法。
• Complex containing a Lewis acid and Brønsted acid for the catalytic reactions of aza-Michael addition
  作者：Xin-xin Mao、Jiao Wang、Qun-hua Xia、Yong-miao Shen

  DOI：10.1134/s0023158411030207

  日期：2011.7

  The novel efficient complex catalyst containing a Lewis acid and a Bronsted acid have been prepared by the reaction of proline ion liquid and cuprous iodide. The catalyst was characterized by FT-IR techniques using pyridine as probe molecule. A fast, mild, and quantitative procedure for aza-Michael addition reactions between various amines and alpha,beta-unsaturated carbonyl compounds and nitriles has been developed using the novel complex catalyst. The results showed that the novel catalyst owned high activities for the reactions with excellent yields within 1 min.
• US4831013A
  申请人：——

  公开号：US4831013A

  公开（公告）日：1989-05-16
• [EN] 2-SUBSTITUTED-E-FUSED-(1,2,4)TRIAZOLO(1,5-C)PYRIMIDINES PHARMACEUTICAL COMPOSITIONS AND USES THEREOF
  申请人：CIBA-GEIGY AG

  公开号：WO1988002370A1

  公开（公告）日：1988-04-07

  (EN) Compounds of formula (I), wherein R1 is optionally substituted phenyl, pyridyl, thienyl, furyl, pyrrolyl, thiazolyl, or ribofuranosyl; X is oxygen, NR, or sulfur; R is hydrogen, lower alkyl, lower alkenyl, or lower alkynyl; and ring A is a) an optionally substituted 5-8 membered monocycloalken-1,2-diyl; b) an optionally substituted carbobicyclic ring of formula (II), wherein n and m are each independently one or two; or c) an optionally substituted 5-6 membered heterocycle having one or two heteroatoms, the atoms of which are selected from carbon, oxygen, nitrogen, and sulfur. Also disclosed are tautomers of the above and pharmaceutically acceptable salts; compositions thereof; and methods of using the compounds, tautomer, or salts.(FR) Composés présentant la formule (I) dans laquelle R1 est, au choix, un phényle substitué, un pyridyle, un thiényle, un furyle, un pyrrolyle, un thiazolyle ou un ribofuranosyle; X est l'oxygène, NR ou le soufre; R est l'hydrogène, un alkyle inférieur, un alcynyle inférieur ou alkyle inférieur; et le cycle A est a) un monocycloalcène-1,2-diyle à 5 à 8 côtés, éventuellement substitué; b) un cycle carbobicyclique, éventuellement substitué, de formule (II) dans laquelle n et m représentent indépendamment 1 ou 2; ou c) un hétérocycle de 5 à 6 côtés éventuellement substitué comprenant un ou deux hétéro-atomes, et dont les atomes sont choisis parmi le carbone, l'oxygène, l'azote et le soufre. Sont également décrits des tautomères de ces composés ainsi que des sels pharmaceutiques; compositions comprenant ces composés et procédés utilisant les composés, leurs tautomères ou leurs sels.