2-[acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]acrylic acid methyl ester | 503073-47-0

• 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: 2-[acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]acrylic acid methyl ester
• 英文别名: methyl 2-[acetyloxy-[3-(4-methylphenyl)-1,2-oxazol-5-yl]methyl]prop-2-enoate
• CAS: 503073-47-0
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: KASXZJIKJYQMPW-UHFFFAOYSA-N

物化性质

• 熔点：
  97-98 °C
• 沸点：
  475.5±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.98
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.63
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-[acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]acrylic acid methyl ester 在 氢氧化钾 、 sodium tetrahydroborate 、 1-羟基苯并三唑 、 达卡巴嗪 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.25h， 生成
  参考文献：
  名称：

  Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity

  摘要：

  The synthesis of isoxazole-based derivatives utilizing Baylis-Hillman chemistry and results of their preliminary bioevaluation as hypolipidemic agents in triton model are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00105-6
• 作为产物：
  描述：

  3-(p-tolyl)isoxazole-5-carbaldehyde 在 吡啶 、 三乙烯二胺 、 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 作用下， 反应 3.5h， 生成 2-[acetoxy-(3-p-tolyl-isoxazol-5-yl)-methyl]acrylic acid methyl ester
  参考文献：
  名称：

  Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity

  摘要：

  The synthesis of isoxazole-based derivatives utilizing Baylis-Hillman chemistry and results of their preliminary bioevaluation as hypolipidemic agents in triton model are described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00105-6

文献信息

• Baylis-Hillman Chemistry in Aqueous Media: A Fast and Practical Approach to the Azides of Baylis-Hillman Adducts in Solution and on Solid Phase
  作者：S. Batra、A. Patra、A. K. Roy、A. P. Bhaduri

  DOI：10.1055/s-2002-34887

  日期：——

  Fast and practical access to azides of Baylis-Hillman adducts, from the corresponding acetates in aqueous media and in excellent yields is described. The solution phase methodology has been successfully translated to the solid phase for applications toward combinatorial synthesis.

  描述了一种快速实用的方法，可以从相应的乙酸酯中在水相介质中高效获取Baylis-Hillman加成物的叠氮化物，产率极高。这种溶液相方法已成功转化为固相，用于组合合成的应用。
• Studies on the catalytic hydrogenation of Baylis–Hillman derivatives of substituted isoxazolecarbaldehydes. Unusual retention of isoxazole ring during Pd–C-promoted hydrogenation of Baylis–Hillman adducts
  作者：R. Saxena、V. Singh、S. Batra

  DOI：10.1016/j.tet.2004.08.068

  日期：2004.11

  Results of the catalytic hydrogenation of Baylis–Hillman adducts obtained from substituted 3-, 4- and 5-isoxazolecarbox-aldehydes and their corresponding acetates in the presence of Raney-Ni and Pd–C are presented. The hydrogenation of Baylis–Hillman adducts of substituted 5-isoxazolecarbaldehydes and 3-isoxazolecarbaldehydes in the presence of Raney-Ni furnishes diastereoselectively syn enaminones

  给出了在阮内镍和钯-碳存在下从取代的3-，4-和5-异恶唑羧醛及其相应的乙酸盐获得的Baylis-Hillman加合物催化加氢的结果。取代的5- isoxazolecarbaldehydes和在阮内镍的存在下3-isoxazolecarbaldehydes的的Baylis-希尔曼加合物的氢化的配料非对映选择性顺式烯胺酮过抗并在硼酸的存在下有利于非对映选择性的添加剂进一步增强顺式异构体，观察到。Pd–C促进的这些底物的氢化也具有非对映选择性，有利于合成异构体，但不发生异恶唑环的氢解。在该氢化中硼酸作为添加剂的存在对非对映选择性没有显着影响。Raney-Ni介导的取代的4-异恶唑甲醛的Baylis-Hillman加合物的加氢反应产生吡啶酮衍生物，而Pd-C促进的同一底物的加氢反应是非对映选择性的，从而提供了所得产物的反异构体。衍生自3-和5-异恶唑甲醛的Baylis-Hillman加合物的烯胺酮可作为α'-羟基-1
• An Alternate Route to Substituted1,4-Pentanedienes through Acetates of Baylis-HillmanAdducts in Aqueous Medium
  作者：Sanjay Batra、Rashmi Saxena、Arundhati Patra

  DOI：10.1055/s-2003-40823

  日期：——

  The acylated Baylis-Hillman adducts have been reacted with α,β-unsaturated ketones, esters and nitriles in the presence of DABCO under aqueous condition as an alternate route towards the synthesis of substituted 1,4-pentanedienes. The plausible mechanism for the course of this reaction has been discussed.

  酰化Baylis-Hillman 加合物与α,β-不饱和酮、酯和腈在DABCO 存在下在水溶液条件下反应，作为合成取代1,4-戊二烯的替代途径。已经讨论了该反应过程的合理机制。
• The Baylis–Hillman chemistry in aqueous media: elucidation of mechanism for synthesis of ether side-product leads to an efficient approach to C–O bond formation
  作者：A Patra、A.K Roy、B.S Joshi、R Roy、S Batra、A.P Bhaduri

  DOI：10.1016/s0040-4020(02)01561-2

  日期：2003.1

  The formation of an ether from the Baylis-Hillman (BH) adduct during the BH reaction of 5-isoxazolecarboxaldehydes is a common phenomenon if the reaction is allowed to proceed for longer periods. The amount of formation of such ethers depends on the acrylates used and is most significant for tert-butyl acrylates. A study of the plausible mechanism for the formation of these side-products led to reactions of acetates of BH adducts with phenol in aqueous media to yield the corresponding 3-phenoxy alk-2-enoates in good yields. The successful translation of solution phase methodology to solid phase for application towards combinatorial chemistry is discussed. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Persistent splenomegaly in an adult female with homozygous sickle cell anemia
  作者：Sompal Singh、Deepak Kumar Singh、Ruchika Gupta、Sonu Nigam、Tejinder Singh

  DOI：10.1080/01650420500328365

  日期：2006.2

  Sickle cell anemia (SCA) is associated with repeated episodes of erythrostasis in the spleen, which lead to thrombosis and infarction of the spleen resulting in "autosplenectomy" which is usually complete by 8 years of age.We present a case of a 22-year-old female who presented with complaints of fever, bone pain and joint swelling. On examination she had pallor, icterus and moderate splenomegaly. Her hemoglobin was 7.5g/dl. Peripheral smear showed many sickled red cells. Slide test for sickling was positive with 2% sodium metabisulphite. Hemoglobin electrophoresis revealed a single band in the hemoglobin S, D, and G region. No band was seen in the HbA & HbA(2) region. HbF level was 0%. USG showed an enlarged spleen with few defined hypoechoeic lesion.We present this case because of rarity of association of homozygous SCA with splenomegaly in this age group, the confusion that echogenic lesions in spleen can create and to emphasize the risk of sequestration crises, which remains in such cases.