2-(4-methylphenyl)-1-(1H-pyrazol-1-yl)ethanone | 1006658-18-9

• 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: 2-(4-methylphenyl)-1-(1H-pyrazol-1-yl)ethanone
• 英文别名: 2-(4-methylphenyl)-1-pyrazol-1-ylethanone
• CAS: 1006658-18-9
• 化学式: C₁₂H₁₂N₂O
• 分子量: 200.24
• InChiKey: MJMKIBBZZBZKHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(4-bromobenzylideneamino)benzothiazole 、 2-(4-methylphenyl)-1-(1H-pyrazol-1-yl)ethanone 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 rac-(2S,3R)-2-(4-bromophenyl)-3-(p-tolyl)-2,3-dihydro-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-one
  参考文献：
  名称：

  非对映体和对映体选择性曼尼希/环化级联反应接近手性苯并噻唑并嘧啶衍生物

  摘要：

  一种有效的不对称曼尼希/环化级联策略是从2-苯并噻唑啉与N-酰基吡唑建立的，以使用铜基络合物提供光学活性的苯并噻唑并嘧啶衍生物。温和的级联过程构建了各种结构多样的产品，具有广泛的底物范围，同时具有出色的对映选择性（高达99％ee）和非对映选择性（高达99：1 dr）。

  DOI：

  10.1002/chem.202005509

文献信息

• Rationally Designed Amide Donors for Organocatalytic Asymmetric Michael Reactions
  作者：Bin Tan、Gloria Hernández-Torres、Carlos F. Barbas

  DOI：10.1002/anie.201200996

  日期：2012.5.29

  Amide nucleophiles on demand: Rationally designed pyrazoleamides function as Michael donors in urea‐catalyzed asymmetric Michael reactions with excellent chemical and optical yields (see scheme). The pyrazoleamide group performs as an ester equivalent, a directing group, an activating group, and functions as a good leaving group in further transformations of the product.

  按需提供酰胺亲核试剂：合理设计的吡唑酰胺在尿素催化的不对称Michael反应中起Michael供体的作用，具有出色的化学和光学收率（请参见方案）。吡唑酰胺基团充当酯当量，指导基团，活化基团，并在产物的进一步转化中充当良好的离去基团。
• An organocatalytic asymmetric Mannich reaction of pyrazoleamides with cyclic trifluoromethyl ketimines: enantioselective access to dihydroquinazolinone skeletons
  作者：Yuan Luo、Ke-Xin Xie、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1039/c8ob00707a

  日期：——

  An organocatalyzed asymmetric Mannich reaction of pyrazoleamides and cyclic trifluoromethyl ketimines with a chiral bifunctional amine-squaramide as the catalyst was developed. A wide range of trifluoromethyl dihydroquinazolinone derivatives bearing adjacent quaternary and tertiary stereogenic centers were readily obtained in good to excellent yields (up to 99%) with high diastereo- and enantioselectivities

  吡唑酰胺和环状三氟甲基酮亚胺的有机催化不对称曼尼希反应，以手性双官能胺-方酸酰胺为催化剂进行了研究。容易获得具有相邻的四级和三级立体异构中心的各种三氟甲基二氢喹唑啉酮衍生物，具有良好的至优异的产率（高达99％），具有高非对映异构和对映选择性（高达99％ee和> 20：1 dr）。还证明了该产品的大规模实验和转化。
• Organocatalytic asymmetric Michael addition of pyrazoleamides to β -phthalimidonitroethene
  作者：Yuan Luo、Ke-Xin Xie、Deng-Feng Yue、Xiao-Mei Zhang、Xiao-Ying Xu、Wei-Cheng Yuan

  DOI：10.1016/j.tet.2017.09.019

  日期：2017.10

  A highly organocatalyzed asymmetric Michael addition reaction of pyrazoleamides to β-phthalimidonitroethene has been developed with a chiral bifunctional thiourea-tertiary amine as the catalyst. A wide range of γ-nitro β-amino amides were readily obtained in good to excellent yields with high diastereo- and enantioselectivities (up to 99% yield, 99% ee and >20:1 dr). The large scale experiment and

  以手性双官能硫脲-叔胺为催化剂，开发了高度有机催化的吡唑酰胺与β-邻苯二甲酰亚胺基硝基乙烯的迈克尔不对称加成反应。容易获得具有高非对映和对映选择性（高至99％收率，99％ee和> 20：1 dr的高非对映选择性）的各种γ-硝基β-氨基酰胺，产率高至优。还证明了该产品的大规模实验和转化。
• ASYMMETRICALLY CATALYZED SYNTHESIS METHOD OF NITROPYRAZOLE AMIDE COMPOUND
  申请人：Zhejiang Jiuzhou Pharmaceutical Co., Ltd.

  公开号：US20170291876A1

  公开（公告）日：2017-10-12

  A synthesis method of γ-nitropyrazole amide compound through asymmetrical catalyzing technique is provided, a nitroalkane and an α,β-unsaturated pyrazole amide are applied as the raw material, a complex formed by a chiral amine oxide with a rare earth metal compound is served as the catalyst, a 4 Å molecular sieve is served as an additive, the γ-nitropyrazole amide compound can be obtained with a yield more than 99% and enantiomeric excess more than 99% ee. The catalytic system not only has the advantages of simple operation, mild reaction conditions, requiring no acid/base additives, convenient product purification, high yield and enatioselectivity, compliance with green atomic economy, and promising prospects for industrial application, but also allows the obtained γ-nitropyrazole amide compound to undergo some simple chemical conversions to produce some molecules having physiological activities.