4-(4-bromophenyl)-4-oxo-2-phenylbutanenitrile | 133131-51-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-(4-bromophenyl)-4-oxo-2-phenylbutanenitrile
• 英文别名: 4-(4-bromo-phenyl)-4-oxo-2-phenyl-butyronitrile；4-(4-Brom-phenyl)-4-oxo-2-phenyl-butyronitril；(+/-)-4-Oxo-2-phenyl-4-(4-brom-phenyl)-buttersaeure-nitril；3-(4-Brom-benzoyl)-2-phenyl-propionitril
• CAS: 133131-51-8
• 化学式: C₁₆H₁₂BrNO
• 分子量: 314.181
• InChiKey: ALNSGKRLPBRPMD-UHFFFAOYSA-N

物化性质

• 熔点：
  124 °C
• 沸点：
  482.6±45.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(4-bromophenyl)-4-oxo-2-phenylbutanenitrile 在 甲醇 、 sodium methylate 作用下， 生成 4-benzo[1,3]dioxol-5-yl-3-(4-bromo-benzoyl)-2-phenyl-crotonic acid
  参考文献：
  名称：

  Allen; Frame, Canadian Journal of Research, 1932, vol. 6, p. 605,611

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氰硅烷 、 1-(4-bromophenyl)-3-phenyl-2-propen-1-one 在 thiourea functionalized magnetic hydroxyapatite 作用下， 以 水 为溶剂， 反应 6.0h， 以96%的产率得到4-(4-bromophenyl)-4-oxo-2-phenylbutanenitrile
  参考文献：
  名称：

  Thiourea-functionalized magnetic hydroxyapatite as a recyclable inorganic–organic hybrid nanocatalyst for conjugate hydrocyanation of chalcones with TMSCN

  摘要：

  The recoverable nanomagnetic catalyst was manufactured based on thiourea modified magnetic hydroxyapatite. Magnetic hydroxyapatite (mHAp) as the inorganic-organic hybrid support was fabricated using co-precipitate condition and then modified via the covalently anchoring of 1-(3,5-bis(trifluoromethyl)phenyl-3-propyl)thiourea. The hybrid nano-catalyst has been identified by TEM, SEM, FTIR, BET, TGA, and XRD. This nanocatalyst appeared efficient and robust in the 1,4-addition reaction of TMSCN to alpha,beta-unsaturated aromatic enones in excellent yields (85-96%) under mild reaction condition and simple work-up process. This recoverable organocatalyst has a great potential as an industrially viable and eco-safe catalyst. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.catcom.2015.08.016

文献信息

• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：ASTRAZENECA AB

  公开号：WO2004011410A1

  公开（公告）日：2004-02-05

  Compounds of formula (I):wherein variable groups are as defined within; for use in the inhibition of 11βHSD1 are described.

  式(I)的化合物：其中变量基团如定义内；用于抑制11βHSD1。
• Cyano-borrowing reaction: nickel-catalyzed direct conversion of cyanohydrins and aldehydes/ketones to β-cyano ketone
  作者：Zhao-Feng Li、Qian Li、Li-Qing Ren、Qing-Hua Li、Yun-Gui Peng、Tang-Lin Liu

  DOI：10.1039/c9sc00640k

  日期：——

  nickel-catalyzed, high atom- and step-economical reaction of cyanohydrins with aldehydes or ketones via an unprecedented “cyano-borrowing reaction” has been developed. Cleavage of the C–CN bond of cyanohydrins followed by aldol condensation and conjugate addition of cyanide to α,β-unsaturated ketones proceeded to deliver a range of racemic β-cyano ketones with good to high yields. The practical procedure

  通过前所未有的“借氰反应” ，氰醇与醛或酮的直接镍催化、高原子和多步经济的反应已被开发出来。氰醇的 C-CN 键断裂，然后是羟醛缩合和氰化物与 α,β-不饱和酮的共轭加成，以良好至高产率提供一系列外消旋 β-氰基酮。使用商业和毒性较低的 CN 源的实际程序预示着该协议的广泛应用。
• Cyanation of α,β-unsaturated enones by malononitrile in open air under metal-catalyst-free conditions
  作者：Shaoxia Lin、Ying Wei、Fushun Liang

  DOI：10.1039/c2cc35528k

  日期：——

  Cyanation of α,β-unsaturated enones by employing malononitrile as the organic cyanation source has been disclosed, which proceeds efficiently at room temperature in open air under metal-catalyst-free conditions.

  已经披露了通过使用氢氰酸腈作为有机氰化源对α,β-不饱和酮进行氰化反应，该反应在常温下在开放空气中，以无金属催化剂的条件高效进行。
• β-AROYL-α- AND -β-ARYLPROPIONIC ACIDS: PART I. THEIR PREPARATION AND LACTONIZATION
  作者：Sayed Sherif

  DOI：10.1139/v61-338

  日期：1961.12.1

  β-p-bromobenzoyl-α- and -β-phenyl-propionic acid, and a mixture of β-p-bromobenzoyl-α- and -β-p-hydroxyphenylpropionic acid, respectively.Similarly, iodobenzene reacts with the same anhydrides to give a mixture of β-p-iodobenzoyl-α- and -β-phenylpropionic acid and β-benzoyl-α- and -β-phenylpropionic acid, and a mixture of β-benzoyl- and β-p-iodobenzoyl-α-p-methoxyphenylpropionic acid, respectively.Phenyl- and diphenyl-succinic

  溴苯在无水氯化铝存在下与苯基和对甲氧基苯基琥珀酸酐反应生成β-对溴苯甲酰基-α-和-β-苯基-丙酸的混合物，以及β-对溴苯甲酰基的混合物-α-和-β-对羟基苯基丙酸，分别。同样，碘苯与相同的酸酐反应得到β-​​对碘苯甲酰-α-和-β-苯基丙酸和β-苯甲酰-α-和-的混合物β-苯基丙酸，以及β-苯甲酰基-和β-对碘苯甲酰基-α-对甲氧基苯基丙酸的混合物。苯基-和二苯基-琥珀酸酐被氯化铝环化成1-酮茚满和1-酮-2-苯基茚满-3-羧酸。上述酮酸通过沸腾乙酸酐转化为β,γ-不饱和γ-内酯。
• [EN] NEW THIADIAZOLES AND OXADIAZOLES AND THEIR USE AS PHOSPHODIESTERASE-7 INHIBITORS<br/>[FR] NOUVEAUX THIADIAZOLES ET OXADIAZOLES ET UTILISATION DE CEUX-CI COMME INHIBITEURS DE LA PHOSPHODIESTERASE DE TYPE 7
  申请人：WARNER LAMBERT CO

  公开号：WO2002028847A1

  公开（公告）日：2002-04-11

  The invention provides 1,3,4-thiadiazoles and 1,3,4-oxadiazoles having the following formula (I):in which, Y is S or O,R1 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl or a polycyclic group, optionally substituted,R2 is alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, cycloalkenyl or aryl optionally substituted,R3 is X2-R'3, in which X2 is a binding group and R'3 is cycloalkyl, heterocycloalkyl, cycloalkenyl, aryl, heteroaryl, or a polycyclic group; optionally substituted,or their pharmaceutically acceptable derivatives,the process for their preparation and their use for the manufacture of a medicament for the treatment of disorders for which a treatment by a PDE7 inhibitor is relevant.

  本发明提供了具有以下式（I）的1,3,4-噻二唑和1,3,4-氧二唑：其中，Y是S或O，R1是烷基，烯基，炔基，环烷基，杂环烷基，环烯基，芳基，杂芳基或多环基，可选择性地取代，R2是烷基，烯基，炔基，环烷基，杂环烷基，环烯基或芳基，可选择性地取代，R3是X2-R'3，其中X2是连接基，R'3是环烷基，杂环烷基，环烯基，芳基，杂芳基或多环基；可选择性地取代，或其药学上可接受的衍生物，其制备方法及其用于制造用于治疗需要通过PDE7抑制剂进行治疗的疾病的药物。