4-(5-chloro-2-nitrophenyl)-4-hydroxy-3-methylenebutan-2-one | 524022-74-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(5-chloro-2-nitrophenyl)-4-hydroxy-3-methylenebutan-2-one
• 英文别名: 3-[(5-chloro-2-nitrophenyl)hydroxymethyl]but-3-en-2-one；3-[(5-Chloro-2-nitrophenyl)-hydroxymethyl]but-3-en-2-one
• CAS: 524022-74-0
• 化学式: C₁₁H₁₀ClNO₄
• 分子量: 255.658
• InChiKey: ICGOTXMRHVFUCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(5-chloro-2-nitrophenyl)-4-hydroxy-3-methylenebutan-2-one 在 盐酸 作用下， 以 乙醇 为溶剂， 以99%的产率得到(Z)-3-(chloromethyl)-4-(5-chloro-2-nitrophenyl)but-3-en-2-one
  参考文献：
  名称：

  2-硝基苯甲醛衍生的 Morita-Baylis-Hillman 加合物作为合成子在类药物支架构建中的探索性应用

  摘要：

  摘要 由 2-硝基苯甲醛前体和丙烯酸甲酯或甲基乙烯基酮制备的 Morita-Baylis-Hillman 加合物已被用作制备 α-[(烷基氨基)甲基]肉桂酸酯及其but-3-en 的关键合成子。 -2-one 类似物、肉桂酸酯-叠氮胸苷 (AZT) 偶联物​​、2-喹诺酮和喹啉衍生物。已经进行了计算机对接研究，以探索肉桂酸酯-AZT 偶联物作为潜在的双重作用 HIV-1 整合酶-逆转录酶 (IN-RT) 抑制剂的潜力。结果进一步证明了 Morita-Baylis-Hillman 方法在构建复杂的类药物支架中的适用性。图形概要

  DOI：

  10.1080/00397911.2018.1559333
• 作为产物：
  描述：

  5-氯-2-硝基苯甲醛 、 丁烯酮 在 三乙烯二胺 作用下， 以 氯仿 为溶剂， 反应 144.0h， 以100%的产率得到4-(5-chloro-2-nitrophenyl)-4-hydroxy-3-methylenebutan-2-one
  参考文献：
  名称：

  Baylis-Hillman方法研究喹啉衍生物。

  摘要：

  2-硝基苯甲醛与各种活化烯烃的Baylis-Hillman反应提供加合物，该加合物经过还原环化生成喹啉衍生物。环化反应的化学和区域选择性似乎受底物和试剂系统选择的影响，并且观察到竞争反应。

  DOI：

  10.1039/b608592j

文献信息

• A Convenient One-Pot Preparation of 2-Methyl-3-(phenylthio- methyl)quinolines from Morita-Baylis-Hillman Adducts and Their Oxidation to the Corresponding Sulfones
  作者：Chintakunta Ramesh、Po-Min Lei、Veerababurao Kavala、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.3390/molecules17055081

  日期：——

  thiols followed by reductive cyclization with Fe/AcOH was developed. The 2-methyl-3-(phenylthiomethyl)quinolines were transformed into 2-methyl-3-(phenylsulfonylmethyl)quinolines via m-CPBA-mediated oxidation.

  开发了一种方便的一锅法从 Morita-BAylis-Hillman 加合物通过硫醇的共轭加成然后用 Fe/AcOH 还原环化制备 2-甲基-3-（苯硫基甲基）喹啉。2-甲基-3-(苯硫甲基)喹啉通过m-CPBA介导的氧化转化为2-甲基-3-(苯磺酰基甲基)喹啉。
• Facile synthesis of biarylmethanes and tetrasubstituted arenes <i>via</i> a base-mediated [3 + 3] benzannulation reaction of Morita–Baylis–Hillman adducts and unsaturated sulfones
  作者：Deepak Yadav、Sunil K. Sharma、Rajeev S. Menon

  DOI：10.1039/c9ob00214f

  日期：——

  A facile DBU-mediated [3 + 3] benzannulation reaction of 1,3-bis-sulfonyl propenes and Morita–Baylis–Hillman (MBH) bromides is described. The benzannulation reaction afforded bis-sulfonyl biarylmethanes/arenes with complete regioselectivity. The products may be converted readily into corresponding benzophenones via site-selective benzylic oxidation.

  描述了一种简单的DBU介导的1，3-双磺酰基丙烯与Morita-Baylis-Hillman（MBH）溴化物的[3 + 3]苯并环反应。苯并环化反应提供具有完全区域选择性的双磺酰基联芳基甲烷/芳烃。产物可以通过位点选择性苄基氧化容易地转化为相应的二苯甲酮。
• Synthesis of Indolylquinolines, Indolylacridines, and Indolylcyclopenta[<i>b</i>]quinolines from the Baylis–Hillman Adducts: An in Situ [1,3]-Sigmatropic Rearrangement of an Indole Nucleus To Access Indolylacridines and Indolylcyclopenta[<i>b</i>]quinolines
  作者：Chintakunta Ramesh、Po-Min Lei、Donala Janreddy、Veerababurao Kavala、Chun-Wei Kuo、Ching-Fa Yao

  DOI：10.1021/jo301313m

  日期：2012.10.5

  A simple and easy route to the synthesis of a variety of structurally diverse indolylquinolines, indolylacridines, and indolylcyclopenta[b]quinoline derivatives via the reductive cyclization of C-alkylated indole derivatives, derived from acyclic as well as cyclic Baylis–Hillman adducts with indoles, is described. An unusual in situ [1,3]-sigmatropic rearrangement of the indole nucleus was observed

  一种简单易行的途径，可通过C-烷基化的吲哚衍生物的还原环化反应，合成各种结构多样的吲哚基喹啉，吲哚基吡啶和吲哚基环戊[ b ]喹啉衍生物，描述。在含有吲哚的α-区域选择性B–H加合物的还原环化过程中，观察到吲哚核的不寻常的原位[1,3]-σ重排，产生吲哚基吡啶和吲哚基环戊[ b ]喹啉衍生物。
• Baylis–Hillman-derived N,N′-disubstituted piperazines: structural and preliminary computational studies
  作者：Kenudi C. Idahosa、Yi-Chen Lee、Dubekile Nyoni、Perry T. Kaye、Mino R. Caira

  DOI：10.1016/j.tetlet.2011.03.133

  日期：2011.6

  Exploratory studies towards the preparation of potential HIV-1 protease and integrase inhibitors have led to the synthesis of Baylis-Hillman-derived N,N'-disubstituted piperazines. X-ray crystallographic, computer modelling and NMR techniques have been used to elucidate questions concerning configurational preferences, reaction pathways and the apparent difference in susceptibility towards aza-Michael reactions exhibited by methyl acrylate and methyl vinyl ketone (MVK) derived Baylis-Hillman substrates. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of 3-substituted-4-hydroxyquinoline N-oxides from the Baylis–Hillman adducts of o-nitrobenzaldehydes
  作者：Ka Young Lee、Jeong Mi Kim、Jae Nyoung Kim

  DOI：10.1016/s0040-4020(02)01518-1

  日期：2003.1

  The reaction of the Baylis-Hillman adducts 1b-f derived from o-nitrobenzaldehydes in trifluoroacetic acid in the presence of triflic acid (0.2 equiv.) afforded 3-substituted-4-hydroxyquinoline N-oxides 2b-e and 2a in good to moderate yields. The reaction mechanism was evidenced by the experiment with 1f, the Baylis-Hillman adduct of 2-nitrobenzaldehyde N-tosylimine, as the one involving N-hydroxyisoxazoline as the key intermediate. (C) 2003 Elsevier Science Ltd. All rights reserved.