N'-(3-chlorophenyl)acetohydrazide | 13123-97-2

• 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: N'-(3-chlorophenyl)acetohydrazide
• CAS: 13123-97-2
• 化学式: C₈H₉ClN₂O
• mdl: MFCD02646910
• 分子量: 184.625
• InChiKey: KEASHJWIKBMFMD-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C
• 沸点：
  245.8±32.0 °C(Predicted)
• 密度：
  1.288±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N'-(3-chlorophenyl)acetohydrazide 在 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 mineral oil 为溶剂， 生成 4-(7-acetyl-8-(3-chlorophenyl)-1-oxa-2,7,8-triazaspiro[4.4]non-2-en-3-yl)benzonitrile
  参考文献：
  名称：

  Synthesis of Spiro-Fused Pyrazolidoylisoxazolines

  摘要：

  Routes to structurally unique spiro-fused pyrazolidoylisoxazolines are reported. These methods start with monosubstituted hydrazines or hydrazides and utilize the nitrile oxide 1,3-dipolar cycloaddition reaction to generate the targeted spiro-fused bis-heterocycles. Molecular shape space diversity analyses were performed on these pyrazolidoylisoxazolines showing that manipulation of the appended R groups significantly changes the molecular shape.

  DOI：

  10.1021/jo200924y
• 作为产物：
  描述：

  乙酸酐 、 间氯苯肼 在 三乙胺 作用下， 以 乙醚 为溶剂， 生成 N'-(3-chlorophenyl)acetohydrazide
  参考文献：
  名称：

  Synthesis of Spiro-Fused Pyrazolidoylisoxazolines

  摘要：

  Routes to structurally unique spiro-fused pyrazolidoylisoxazolines are reported. These methods start with monosubstituted hydrazines or hydrazides and utilize the nitrile oxide 1,3-dipolar cycloaddition reaction to generate the targeted spiro-fused bis-heterocycles. Molecular shape space diversity analyses were performed on these pyrazolidoylisoxazolines showing that manipulation of the appended R groups significantly changes the molecular shape.

  DOI：

  10.1021/jo200924y

文献信息

• Synthesis and Biological Evaluation of the 1-Arylpyrazole Class of σ₁ Receptor Antagonists: Identification of 4-{2-[5-Methyl-1-(naphthalen-2-yl)-1<i>H</i>-pyrazol-3-yloxy]ethyl}morpholine (S1RA, E-52862)
  作者：José Luis Díaz、Rosa Cuberes、Joana Berrocal、Montserrat Contijoch、Ute Christmann、Ariadna Fernández、Adriana Port、Jörg Holenz、Helmut Buschmann、Christian Laggner、Maria Teresa Serafini、Javier Burgueño、Daniel Zamanillo、Manuel Merlos、José Miguel Vela、Carmen Almansa

  DOI：10.1021/jm3007323

  日期：2012.10.11

  yl}morpholine (S1RA, E-52862), which showed high activity in the mouse capsaicin model of neurogenic pain, emerged as the most interesting candidate. In addition, compound 28 exerted dose-dependent antinociceptive effects in several neuropathic pain models. This, together with its good physicochemical, safety, and ADME properties, led compound 28 to be selected as clinical candidate.

  合成和一系列新的1-芳基吡唑作为有效的σ的药理活性1（σ受体1个R）报道拮抗剂。新化合物在体外进行了评价在人σ 1 R和豚鼠σ 2受体（σ 2 R）结合测定。吡唑取代基的性质对于活性至关重要，并且根据已知的受体药效基团，碱性胺被证明是必需的。各种各样的氨基和吡唑基团之间胺和间隔的长度被容忍，但只有亚乙氧基间隔物和小环胺具有足够的选择性的化合物为σ 1 - [R VSσ 2R.最选择性化合物进一步成型，和化合物28，4- 2- [5-甲基-1-（萘-2-基）-1- ħ吡唑-3-基氧基]乙基}吗啉（S1RA，E -52862）在小鼠辣椒素神经性疼痛模型中表现出高活性，因此成为最有趣的候选药物。另外，化合物28在几种神经性疼痛模型中具有剂量依赖性的镇痛作用。加上其良好的物理化学，安全性和ADME特性，使得化合物28被选为临床候选药物。
• Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with <i>N′</i> -Acyl Arylhydrazines
  作者：Jun Cao、Zi-Li Chen、Shu-Min Li、Gao-Feng Zhu、Yuan-Yong Yang、Cong Wang、Wen-Zhang Chen、Jian-Ta Wang、Ji-Quan Zhang、Lei Tang

  DOI：10.1002/ejoc.201800374

  日期：2018.6.15

  An efficient and ligand‐free palladium‐catalyzed arylation of benzofurans has been developed with N′ ‐acyl arylhydrazines as the coupling partners. This protocol features a wide functional‐group tolerance and highly regioselective products.

  已开发出一种高效且无配体的钯催化苯并呋喃芳基化反应，以 N'-酰基芳基肼作为偶联伙伴。该协议具有广泛的官能团耐受性和高度区域选择性的产品。
• Synthesis of 2,3-dihydro-1H-indazoles by Rh(iii)-catalyzed C–H cleavage of arylhydrazines
  作者：Jinzhong Yao、Ruokun Feng、Cong Lin、Zhanxiang Liu、Yuhong Zhang

  DOI：10.1039/c4ob00921e

  日期：——

  A rhodium-catalyzed efficient method for the synthesis of 2,3-dihydro-1H-indazoles is described. The reaction of arylhydrazines with olefins results in the corresponding 2,3-dihydro 1H-indazoles with exclusive regioselectivity via C–H bond activation. The utility of the methodology is illustrated by a rapid synthesis of 1H-indazoles under mild reaction conditions in half an hour.

  描述了一种高效的铑催化法合成2,3-二氢-1H-吲哚唑。芳基肼与烯烃的反应通过C–H键活化，产生相应的2,3-二氢-1H-吲哚唑，具备专一的区域选择性。该方法的实用性通过在温和反应条件下快速合成1H-吲哚唑，时间仅需半小时得以展示。
• Palladium/copper-catalyzed arylation of alkenes with N′-acyl arylhydrazines
  作者：Ji-Quan Zhang、Jun Cao、Wei Li、Shu-Min Li、Yong-Kang Li、Jian-Ta Wang、Lei Tang

  DOI：10.1039/c6nj03718f

  日期：——

  A novel ligand-free palladium/copper-catalyzed Heck-type coupling reaction of alkenes and N′-acyl arylhydrazines has been developed by using air as the terminal oxidant. This protocol features wide functional group tolerance and produces highly chemoselective and regioselective products with good to excellent yields.

  通过使用空气作为末端氧化剂，开发了一种新型的无配体的钯/铜催化的烯烃与N'-酰基芳基肼的Heck型偶联反应。该方案具有宽泛的官能团耐受性，可产生高化学选择性和区域选择性产物，并具有良好或优异的产率。
• Synthesis of 1<i>H</i>-Indole-2,3-dicarboxylates via Rhodium-Catalyzed C–H Annulation of Arylhydrazines with Maleates
  作者：Sheng Zhang、He Li、Yoshinori Yamamoto、Ming Bao

  DOI：10.1021/acs.joc.0c01727

  日期：2020.10.2

  This work describes a one-step synthesis of 1H-indole-2,3-dicarboxylates through C–H activation. Rhodium-catalyzed tandem C–H activation and annulation of 2-acetyl-1-phenylhydrazines with maleates proceeded smoothly in the presence of additive NaOAc and oxidant Ag2CO3 and produced the corresponding indole derivatives, 1H-indole-2,3-dicarboxylates, in satisfactory to good yields. A variety of useful

  这项工作描述了通过C–H活化的1 H-吲哚-2,3-二羧酸酯的一步合成。在添加剂NaOAc和氧化剂Ag 2 CO 3的存在下，铑催化的串联C–H活化和2-乙酰基-1-苯基肼与马来酸酯的环合反应顺利进行，并产生了相应的吲哚衍生物1 H-吲哚-2,3-二羧酸盐，令人满意的好收率。苯环上可耐受各种有用的官能团，包括卤素原子（F，Cl，Br和I）和甲氧羰基。