3-chloro-2-methylpent-2-enal | 31357-76-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-chloro-2-methylpent-2-enal
• 英文别名: (E)-3-chloro-2-methyl-pent-2-enal；(E)-3-chloro-2-methylpent-2-enal
• CAS: 31357-76-3
• 化学式: C₆H₉ClO
• 分子量: 132.59
• InChiKey: XVBAOJCDXBMWMR-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-甲基-6-甲基氨基尿嘧啶 、 3-chloro-2-methylpent-2-enal 以59%的产率得到
  参考文献：
  名称：

  YONEDA, FUMIO;KOGA, MASAKAZU;NAGAMATSU, TOMOHISA, SYNTHESIS, BRD, 1983, N 1, 75-76

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-4-methylhex-4-en-3-one 在 五氯化磷 、 potassium tert-butylate 、 臭氧 作用下， 以 正戊烷 为溶剂， 反应 48.0h， 生成 3-chloro-2-methylpent-2-enal
  参考文献：
  名称：

  Griesbaum, Karl; Bandyopadhyay, Ashis R.; Meister, Martin, Canadian Journal of Chemistry, 1986, vol. 64, p. 1553 - 1559

  摘要：

  DOI：

文献信息

• Efficient Synthesis of 4- and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines
  作者：Anna S. Komendantova、Alexander V. Komkov、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1002/ejoc.201700737

  日期：2017.8.10

  A general, practical and simple synthesis of functionalized 2-aminopyrimidines starting from β-chlorovinyl aldehydes and amidines is reported. In the presence of potassium carbonate, various ketones have been efficiently incorporated into the pyrimidine derivatives by two-step sequence involving the Vilsmeier-Haack reaction followed by the condensation with guanidines. The protocol is distinguished

  据报道，从β-氯乙烯基醛和am开始的官能化的2-氨基嘧啶的一般，实用和简单的合成。在碳酸钾的存在下，通过涉及维斯迈尔-哈克（Vilsmeier-Haack）反应，然后与胍缩合的两步顺序，各种酮已被有效地掺入嘧啶衍生物中。该协议的特点是操作简便，试剂价格低廉和官能团耐受性强。在许多情况下，无需使用柱色谱法即可以高至极好的收率获得纯净的固体产品。该方法的合成价值通过甾族嘧啶和抗肿瘤药Imatinib和Mocetinostat的前体的有效合成得到证明。
• A Straightforward Approach toward Multifunctionalized Pyridazines via Imination/Electrocyclization
  作者：Alexander V. Komkov、Anna S. Komendantova、Leonid G. Menchikov、Elena I. Chernoburova、Yulia A. Volkova、Igor V. Zavarzin

  DOI：10.1021/acs.orglett.5b01718

  日期：2015.8.7

  A facile synthesis of functionalized 3-carbamide pyridazines starting from readily available chlorovinyl aldehydes and oxamic acid thiohydrazides via cascade imination/electrocyclization is reported. In the presence of p-toluenesulfuric acid, various ketones have been efficiently incorporated into the pyridazine derivatives through a two-step sequence involving a VilsmeierHaack reaction and imination. The synthetic value of this method has been demonstrated by efficient synthesis of steroidal pyridazines.
• Synthesis, characterization and <i>in vivo</i> antitumor effect of new α,β-unsaturated-2,5-disubstituted-1,3,4-oxadiazoles
  作者：M. Fray、I. ELBini-Dhouib、I. Hamzi、R. Doghri、N. Srairi-Abid、D. Lesur、M. Benazza、R. Abidi、T. Barhoumi-Slimi

  DOI：10.1080/00397911.2022.2053993

  日期：2022.3.19
• SUBSTITUIERTE PYRIDO 2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONE
  申请人：BASF Aktiengesellschaft

  公开号：EP0556225A1

  公开（公告）日：1993-08-25
• [EN] SUBSTITUTED PYRIDO[2,3-d]PYRIMIDIN-2,4(1H,3H)-DIONES
  申请人：——

  公开号：WO1992008719A1

  公开（公告）日：1992-05-29

  [FR] Des pyrido[2,3-d]pyrimidin-2,4(1H,3H)-diones ont la formule (Ia) et (Ib), dans lesquelles R1, R2 désignent H, alkyle, cycloalkyle substitués ou non; R3 désigne H, alkyle substitué ou non; R4 désigne H, alkyle, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, cyano ou aminocarbonyle; ou R3 et R4 désignent ensemble alcylène, alcénylène ou 1,2-phénylène; R5 désigne H, alkyle, cyano, C(O)R7, C(S)R7; R6 désigne alkyle, aralcényle, aryle ou hétaryle éventuellement substitués, CH2R8, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, OH, SH, alcoxyle, alkylthio, NH2, alkylamino, NHCXR9, NHSO2R10; R5 et R6 désignent ensemble alcylène, alcénylène ou 1,2-phénylène éventuellement substitués pouvant également contenir des groupes carbonyles ou thiocarbonyles; R7 désigne H, alkyle, OH, SH, alcoxyle, alkylthio, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle, NH2, alkylamino, dialkylamino, aryle ou arylamino éventuellement substitués; R8 désigne halogène, OH, SH, alcoxyle, alkylthio, alcoxycarbonyle, (alkylthio)carbonyle, alcoxy(thiocarbonyle), (alkylthio)thiocarbonyle ou la formule (a); R9 désigne alkyle, alkyle halogène, NR1R2 ou OR1; R10 désigne alkyle, aryle substitué ou non, R11 désigne halogène, OH, SH, alcoxyle, alkylthio, alkyle, nitro ou amino; X désigne oxygène ou soufre. L'invention concerne ces composés, ainsi que leurs sels utilisables en agriculture, qui contiennent un substituant azotique ou hydroxyle, et des herbicides qui contiennent des dérivés d'acide propionique ou phénoxyacétique 2-[4-(hétéro)-aryloxyle] et/ou des dérivés de cyclohexenone en tant que substances herbicides actives et des pyrido[2,3-d]pyrimidin-2,4(1H, 3H)-diones, ainsi que, dans le cas où des groupes terminaux acides ou des atomes basiques d'azote sont présents, les sels de (Ia) ou de (Ib) en tant qu'antidotes.
  [EN] Pyrido[2,3-d]pyrimidin-2,4(1H,3H)-diones are disclosed, having formulas (Ia) and (Ib), in which R?1 and R?2 stand for H, substituted or unsubstituted alkyl, cycloalkyl; R?3 stands for H, substituted or unsubstituted alkyl; R?4 stands for H, alkyl, alkoxycarbonyl, (alkylthio)carbonyl, alkoxy(thiocarbonyl), (alkylthio)thiocarbonyl, cyano or aminocarbonyl; or R?3 and R?4 represent together alkylene, alkenylene or 1,2-phenylene; R?5 stands for H, alkyl, cyano, C(O)R?7; R?6 stands for alkyl, possibly substituted aralkenyl, aryl or hetaryl, CH2?R?8, alkoxycarbonyl, (alkylthio)carbonyl, alkoxy(thiocarbonyl), (alkylthio)thiocarbonyl, OH, SH, alkoxy, alkylthio, NH2?, alkylamino, NHCXR?9, NHSO2?R?10; R?5 and R?6 represent together substituted alkylene, alkenylene or 1,2-phenylene, which may also contain carbonyl or thiocarbonyl groups; R?7 stands for H, alkyl, OH, SH, alkoxy, alkylthio, alkoxycarbonyl, (alkylthio)carbonyl, alkoxy(thiocarbonyl), (alkylthio)thiocarbonyl, NH2? alkylamino, dialkylamino, possibly substituted aryl or arylamino; R?8 stands for halogen, OH, SH, alkoxy, alkylthio, alkoxycarbonyl, (alkylthio)carbonyl, alkoxy(thiocarbonyl), (alkylthio)thiocarbonyl or the formula (a); R?9 stands for alkyl, halogen alkyl, NR?1R?2 or OR?1; R?10 stands for alkyl, substituted or unsubstituted aryl; R?11 stands for halogen, OH, SH, alkoxy, alkylthio, alkyl, nitro or amino; X stands for oxygen or sulphur. Also disclosed are the salts of compounds (Ia) and (Ib) that can be used in agriculture and that contain nitrogen or hydroxy substituants, as well as herbicides that contain 2-[4-(hetero)-aryloxy]-phenoxyacetic acid or propionic acid derivates and/or cyclohexenone derivates as active herbicidal substances and substituted pyrido[2,3-d[pyrimidin-2,4(1H, 3H)-diones, as well as the salts of (Ia) or (Ib) as antidotes when acid end groups or basic nitrogen atoms are present.