2-氯-1-(2-羟基-3-甲基苯基)乙酮 | 75717-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-氯-1-(2-羟基-3-甲基苯基)乙酮
• 英文名称: 2-chloro-1-(2-hydroxy-3-methylphenyl)ethanone
• 英文别名: 2-chloro-1-(2-hydroxy-3-methyl-phenyl)-ethanone；2-Chlor-1-(2-hydroxy-3-methyl-phenyl)-aethanon；2-(2-chloroacetyl)-6-methylphenol
• CAS: 75717-51-0
• 化学式: C₉H₉ClO₂
• 分子量: 184.622
• InChiKey: FZEGRRITIJHDKE-UHFFFAOYSA-N

物化性质

• 熔点：
  65.5-66.5 °C
• 沸点：
  284.5±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-氯-1-(2-羟基-3-甲基苯基)乙酮 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以43%的产率得到7-甲基苯并呋喃-3(2H)-酮
  参考文献：
  名称：

  Rational Evolution of a Novel Type of Potent and Selective Proviral Integration Site in Moloney Murine Leukemia Virus Kinase 1 (PIM1) Inhibitor from a Screening-Hit Compound

  摘要：

  Serine/threonine kinase PIM1 is an emerging therapeutic target for hematopoietic and prostate cancer therapy. To develop a novel PIM1 inhibitor, we focused on 1, a metabolically labile, nonselective kinase inhibitor discovered in our previous screening study. We adopted a rational optimization strategy based mainly on structural information for the PIM1-1 complex to improve the potency and selectivity. This approach afforded the potent and metabolically stable PIM1-selective inhibitor 14, which shows only a marginal increase in molecular weight compared with 1 but has a significantly decreased cLogP. The validity of our design concept was confirmed by X-ray structure analysis. In a cellular study, 14 potently inhibited the growth of human leukemia cell line MV4-11 but had a negligible effect on the growth of WI-38 (surrogate for general toxicity). These results demonstrate the effectiveness of our design strategy for evolving the screening-hit compound 1 into a novel type of PIM1 inhibitor, 14.

  DOI：

  10.1021/jm3001289
• 作为产物：
  描述：

  chloro-acetic acid o-tolyl ester 在 三氯化铝 作用下， 生成 2-氯-1-(2-羟基-3-甲基苯基)乙酮
  参考文献：
  名称：

  Ishikawa; Kurosawa, Nippon Kagaku Kaishi/Journal of the Chemical Society of Japan, 1942, vol. 63, p. 1265

  摘要：

  DOI：

文献信息

• Total synthesis of malyngamide M and isomalyngamide M
  作者：Jie Chen、Zi-Fa Shi、Ling Zhou、An-Le Xie、Xiao-Ping Cao

  DOI：10.1016/j.tet.2010.03.004

  日期：2010.5

  The stereoselective synthesis of malyngamide M (1) was accomplished in nine steps from o-cresol in 12% overall yield. The key steps involved the Wittig reaction of an α-NHBoc aryl ketone 4 for the introduction of vinyl chloride functionality, an amidation of lyngbic acid 3 with a secondary amine 2 for the framework of target molecule, and an isomerization of a (Z)-vinyl chloride to the (E)-configuration

  麦芽酰胺M（1）的立体选择性合成是从邻甲酚开始的9个步骤，总产率为12％。关键步骤包括用于引入氯乙烯官能团的α- NHBoc芳基酮4的Wittig反应，针对目标分子框架的lyngbic acid 3与仲胺2的酰胺化以及（Z）-的异构化使用二苯甲酮作为光敏剂将氯乙烯制成（E）-构型。还合成了异麦芽酰胺M（Z - 1）。
• Anticancer agent
  申请人：Nagano Tetsuo

  公开号：US09156827B2

  公开（公告）日：2015-10-13

  An anticancer agent comprising a compound represented by the formula (I) [R1 represents hydrogen atom, hydroxyl group, a C1-6 alkoxy group and the like; R2 and R3 represents hydrogen atom, a halogen atom, a C1-6 alkyl group and the like; R4 represents hydrogen atom, a C1-6 alkyl group, a C1-6 alkylsulfonyl group and the like; R5 represents hydrogen atom or a substituent; represents a single bond or a double bond; R6 and R7 represents hydrogen atom, a C1-6 alkyl group and the like; R8 represents hydrogen atom, a C1-6 alkyl group and the like; A represents —O—, —S—, or —CH2—; D represents —C═ or —N═; X represents methylene group, —O—, or —CO—; Q represents —N═ or —C(R8)═; and Y represents a heterocyclic group or amino group], which shows a superior inhibitory activity against pim-1 kinase.

  一种抗癌剂，包括由公式（I）所代表的化合物 [ R1 代表氢原子、羟基、C1-6烷氧基等； R2 和 R3 代表氢原子、卤素原子、C1-6烷基等； R4 代表氢原子、C1-6烷基、C1-6烷基磺酰基等； R5 代表氢原子或取代基； 表示单键或双键； R6 和 R7 代表氢原子、C1-6烷基等； R8 代表氢原子、C1-6烷基等； A 代表-O-、-S-或-CH2-； D 代表-C═或-N═； X 代表亚甲基基、-O-或-CO-； Q 代表-N═或-C(R8)═； Y 代表杂环基或氨基]，该化合物对pim-1激酶具有卓越的抑制活性。
• NOVEL PROCESS FOR SYNTHESIZING 2-HALOACETYLPHENOLS
  申请人：SHIONOGI SEIYAKU KABUSHIKI KAISHA

  公开号：EP0043861A1

  公开（公告）日：1982-01-20

  novel process for synthesizing a 2-haloacetylphenol represented by the following general formula: (wherein Y represents a halogen atom, m represents an integer of 0 to 2, X represents a hydrogen atom, C1 to C5 alkyl, C3 to C6 cycloalkyl, C, to C5 alkoxy or a halogen atom, and n represents an integer of 0 to 2), which comprises reacting a phenol represented by the following general formula: (wherein X and n are the same as defined above) with a haloacetonitrile and a boron halide compound in the presence of a bonding aid.

  合成由以下通式表示的 2-卤代乙酰基酚的新工艺： (其中Y代表卤原子，m代表0至2的整数，X代表氢原子、C1至C5烷基、C3至C6环烷基、C, 至C5烷氧基或卤原子，n代表0至2的整数)，该工艺包括将下式通式代表的苯酚与卤代乙腈和卤化硼反应(其中X和n与上式定义相同)： (其中 X 和 n 与上述定义相同）与卤乙腈和卤化硼化合物在助键剂存在下进行反应。
• ANTICANCER AGENT
  申请人：The University of Tokyo

  公开号：EP2565192B9

  公开（公告）日：2015-11-25
• Bigi, Franca; Maggi, Raimondo; Sartori, Giovanni, Gazzetta Chimica Italiana, 1992, vol. 122, # 8, p. 283 - 289
  作者：Bigi, Franca、Maggi, Raimondo、Sartori, Giovanni、Casnati, Giuseppe、Bocelli, Gabriele

  DOI：——

  日期：——