(Z)-2-methyl-4-[3-(trifluoromethyl)benzylidene]-5(4H)-oxazolone | 564441-49-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (Z)-2-methyl-4-[3-(trifluoromethyl)benzylidene]-5(4H)-oxazolone
• 英文别名: (4Z)-2-methyl-4-[[3-(trifluoromethyl)phenyl]methylidene]-1,3-oxazol-5-one
• CAS: 564441-49-2
• 化学式: C₁₂H₈F₃NO₂
• 分子量: 255.196
• InChiKey: XOHSAZSOOSDQPN-POHAHGRESA-N

物化性质

• 熔点：
  123.5-124.5 °C(Solv: chloroform (67-66-3); hexane (110-54-3))
• 沸点：
  302.5±52.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (Z)-2-methyl-4-[3-(trifluoromethyl)benzylidene]-5(4H)-oxazolone 在 sodium hydroxide 、 盐酸 作用下， 反应 5.0h， 生成 m-(trifluoromethyl)phenylpuruvic acid
  参考文献：
  名称：

  Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment

  摘要：

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.08.024
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 、 N-乙酰甘氨酸 在 sodium acetate 、 乙酸酐 作用下， 以47%的产率得到(Z)-2-methyl-4-[3-(trifluoromethyl)benzylidene]-5(4H)-oxazolone
  参考文献：
  名称：

  Maekawa, Kei; Kajiwara, Hiroo; Iseya, Yoshiyuki, Heterocycles, 2003, vol. 60, # 3, p. 637 - 654

  摘要：

  DOI：

文献信息

• Synthesis of Indole-2-carboxylate Derivatives via Palladium-Catalyzed Aerobic Amination of Aryl C–H Bonds
  作者：Kyle Clagg、Haiyun Hou、Adam B. Weinstein、David Russell、Shannon S. Stahl、Stefan G. Koenig

  DOI：10.1021/acs.orglett.6b01592

  日期：2016.8.5

  A direct oxidative C–H amination affording 1-acetyl indolecarboxylates starting from 2-acetamido-3-arylacrylates has been achieved. Indole-2-carboxylates can be targeted with a straightforward deacetylation of the initial reaction products. The C–H amination reaction is carried out using a catalytic Pd(II) source with oxygen as the terminal oxidant. The scope and application of this chemistry is demonstrated

  已经实现了从 2-乙酰氨基-3-芳基丙烯酸酯开始直接氧化 C-H 胺化，得到 1-乙酰基吲哚甲酸酯。通过对初始反应产物进行直接脱乙酰化，可以靶向 2-吲哚羧酸酯。 C-H 胺化反应是使用催化 Pd(II) 源和氧气作为末端氧化剂进行的。这种化学的范围和应用已被证明对于许多富电子和贫电子底物具有良好到高的产率。所选产物通过铃木芳基化和脱乙酰化进行进一步反应，获得高度功能化的吲哚结构。
• Potent, Selective Tetrahydro-β-carboline Antagonists of the Serotonin 2B (5HT_2B) Contractile Receptor in the Rat Stomach Fundus
  作者：James E. Audia、Deborah A. Evrard、Gwyn R. Murdoch、James J. Droste、Jeffrey S. Nissen、Kathy W. Schenck、Pawel Fludzinski、Virginia L. Lucaites、David L. Nelson、Marlene L. Cohen

  DOI：10.1021/jm960062t

  日期：1996.1.1

  A series of potent, selective 5HT(2B) receptor antagonists has been identified based upon yohimbine, with SAR studies resulting in a 1000-fold increase in 5HT(2B) receptor affinity relative to the starting structure (-log K(B)s > 10.0 have been obtained). These high-affinity tetrahydro-beta-carboline antagonists are able to discriminate among the 5HT(2) family of serotonin receptors, with members of the series showing selectivities of more than 100-fold versus both the 5HT(2A) and 5HT(2C) receptors based upon radioligand binding and functional assays. As the first compounds reported with such selectivity and enhanced receptor affinity, these tetrahydro-beta-carboline antagonists are useful tools for elucidating the role of serotonin acting at the 5HT(2B) receptor in normal and disease physiology.
• Maekawa, Kei; Kajiwara, Hiroo; Iseya, Yoshiyuki, Heterocycles, 2003, vol. 60, # 3, p. 637 - 654
  作者：Maekawa, Kei、Kajiwara, Hiroo、Iseya, Yoshiyuki、Igarashi, Tetsutaro、Sakurai, Tadamitsu

  DOI：——

  日期：——
• “Pictet-Spengler-like” Synthesis of Tetrahydro-β-carbolines under Hydrolytic Conditions. Direct Use of Azalactones as Phenylacetaldehyde Equivalents
  作者：James E. Audia、James J. Droste、Jeffrey S. Nissen、Gwyn L. Murdoch、Deborah A. Evrard

  DOI：10.1021/jo9600868

  日期：1996.1.1
• Synthesis and activity of novel analogs of hemiasterlin as inhibitors of tubulin polymerization: modification of the A segment
  作者：Ayako Yamashita、Emily B. Norton、Joshua A. Kaplan、Chuan Niu、Frank Loganzo、Richard Hernandez、Carl F. Beyer、Tami Annable、Sylvia Musto、Carolyn Discafani、Arie Zask、Semiramis Ayral-Kaloustian

  DOI：10.1016/j.bmcl.2004.08.024

  日期：2004.11

  Analogs of hemiasterlin (1) and HTI-286 (2), which contain various aromatic rings in the A segment, were synthesized as potential inhibitors of tubulin polymerization. The structure-activity relationships related to stereo- and regio-chemical effects of substituents on the aromatic ring in the A segment were studied. Analogs, which carry a meta-substituted phenyl ring in the A segment show comparable activity for inhibition of tubulin polymerization to 2, as well as in the cell proliferation assay using KB cells containing P-glycoprotein, compared to those of 1 and 2. (C) 2004 Elsevier Ltd. All rights reserved.