2-[Acetoxy-(5-methyl-3-phenyl-isoxazol-4-yl)-methyl]-acrylic acid methyl ester | 798555-70-1

• 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-(5-methyl-3-phenyl-isoxazol-4-yl)-methyl]-acrylic acid methyl ester
• 英文别名: Methyl 2-[acetyloxy-(5-methyl-3-phenyl-1,2-oxazol-4-yl)methyl]prop-2-enoate
• CAS: 798555-70-1
• 化学式: C₁₇H₁₇NO₅
• 分子量: 315.326
• InChiKey: ALNKYJLDTWOQMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-[Acetoxy-(5-methyl-3-phenyl-isoxazol-4-yl)-methyl]-acrylic acid methyl ester 在 三乙烯二胺 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 生成 5-Hydroxy-2-methylene-3-(5-methyl-3-phenyl-isoxazol-4-yl)-hexanoic acid
  参考文献：
  名称：

  Persistent splenomegaly in an adult female with homozygous sickle cell anemia

  摘要：

  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.

  DOI：

  10.1080/01650420500328365
• 作为产物：
  描述：

  2-{Acetoxy-[3-(2-bromo-phenyl)-5-methyl-isoxazol-4-yl]-methyl}-acrylic acid methyl ester 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以42%的产率得到4-acetoxy-3-methyl-5,6-dihydro-4H-2-oxa-1-aza-benzo[e]azulene-5-carboxylic acid methyl ester
  参考文献：
  名称：

  Tributyltin hydride-mediated straightforward synthesis of a new isoxazolo-benzazulene ring system

  摘要：

  Tributyltin hydride-mediated straightforward synthesis of a new isoxazolo-benzazulene system from the derivatives afforded by the Baylis-Hillman reaction of 3-(2-bromophenyl)-4-isoxazolecarbaldehydes is described. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.07.106

文献信息

• Antileishmanial assessment of isoxazole derivatives against <i>L. donovani</i>
  作者：Sushobhan Mukhopadhyay、Dinesh S. Barak、R. Karthik、Sarvesh K. Verma、Rabi S. Bhatta、Neena Goyal、Sanjay Batra

  DOI：10.1039/d0md00083c

  日期：——

  The antileishmanial activity of a variety of 3-nitro and 3-amino-isoxazoles against promastigote and amastigote stages of L. donovani is described.

  描述了多种3-硝基和3-氨基异噁唑对唐氏利什曼原虫旋毛虫和无毛虫阶段的抗利什曼活性。
• Unusual retention of isoxazole ring under the influence of 3-(substituted nitrophenyl)-2-isoxazoline during catalytic hydrogenation of isoxazoline-substituted isoxazole systems
  作者：Vijay Singh、Samiran Hutait、Gaya P. Yadav、Prakas R. Maulik、Sanjay Batra

  DOI：10.1002/jhet.87

  日期：2009.7

  The cleavage of the isoxazole ring during the Raney-Ni-promoted catalytic hydrogenation is prevented under the influence of 3-(substituted nitrophenyl)-2-isoxazoline in isoxazoline-substituted isoxazole systems produced via 1,3-dipolar cycloaddition either on the Baylis–Hillman derivatives or Grignard products. Unexpectedly, the hydrogenations in these diastereomeric compounds were observed to exclusively

  在阮内镍促进的催化加氢过程中，在3-（取代的硝基苯基）-2-异恶唑啉的影响下，异恶唑环的裂解被阻止，该异恶唑啉取代的异恶唑系统是通过在Baylis上的1，3-偶极环加成生成的异恶唑啉取代的异恶唑系统希尔曼衍生品或格利雅产品。出乎意料的是，观察到这些非对映体化合物中的氢化仅产生产物，其中甲氧基羰基和羟基或乙酰基彼此同义地存在。J.杂环化​​学，（2009）。
• 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