Methyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate | 337355-83-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: Methyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate
• 英文别名: methyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate
• CAS: 337355-83-6
• 化学式: C₁₄H₁₃NO₄
• 分子量: 259.262
• InChiKey: IDWPCXHXUUPEFF-UHFFFAOYSA-N

物化性质

• 沸点：
  467.7±45.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  72.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Methyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、206.84 kPa 条件下， 生成 3-hydroxy-2-methyl-3-(3-phenylisoxazol-5-yl)propionic acid methyl ester
  参考文献：
  名称：

  取代异恶唑甲醛的Baylis-Hillman衍生物的催化加氢研究。Pd-C促进的Baylis-Hillman加合物加氢过程中异恶唑环的异常保留

  摘要：

  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

  DOI：

  10.1016/j.tet.2004.08.068
• 作为产物：
  描述：

  3-苯基异噁唑-5-甲醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 反应 0.58h， 以80%的产率得到Methyl 2-[hydroxy-(3-phenyl-1,2-oxazol-5-yl)methyl]prop-2-enoate
  参考文献：
  名称：

  5-Isoxazolecarboxaldehyde: A Novel Substrate for Fast Baylis-Hillman Reaction

  摘要：

  3-Aryl-5-isoxazolecarboxaldehyde 与多种活化烯发生快速 Baylis-Hillman 反应，生成相应的加合物，收率极高。此处报告的一些 Baylis-Hillman 加合物随后经过改性，得到了异噁唑取代的吡唑啉-3-酮和δ-丁内酯。

  DOI：

  10.1055/s-2001-10815

文献信息

• 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）。
• NaBH₄-mediated FacileReduction of Esters of Baylis-Hillman Adducts: An EfficientApproach to Substituted Propane-1,3-Diols
  作者：Sanjay Batra、Arundhati Patra、Amiya P. Bhaduri

  DOI：10.1055/s-2003-40992

  日期：——

  Reduction of the ester group in the Baylis-Hillman adductsby NaBH4 reduction is facilitated by the secondary hydroxyl grouppresent at their β-position. This method is efficient forthe preparation of substituted propane-1,3-diols.

  通过 NaBH4 还原法还原 Baylis-Hillman 加合物中的酯基时，其 δ 位上存在的仲羟基会起到促进作用。这种方法可以有效地制备取代的丙烷-1,3-二醇。
• 5-Isoxazolecarboxaldehyde: A Novel Substrate for Fast Baylis-Hillman Reaction
  作者：Arundhati Patra、Sanjay Batra、Bijoy Kundu、Bhawani Shankar Joshi、Raja Roy、Amiya Prasad Bhaduri

  DOI：10.1055/s-2001-10815

  日期：——

  3-Aryl-5-isoxazolecarboxaldehyde undergoes fast Baylis-Hillman reaction with a variety of activated alkenes to yield the corresponding adducts in excellent yields. Some of the Baylis-Hillman adducts reported herein have been subsequently modified to obtain isoxazole substituted pyrazolin-3-ones and γ-butyrolactones.

  3-Aryl-5-isoxazolecarboxaldehyde 与多种活化烯发生快速 Baylis-Hillman 反应，生成相应的加合物，收率极高。此处报告的一些 Baylis-Hillman 加合物随后经过改性，得到了异噁唑取代的吡唑啉-3-酮和δ-丁内酯。
• Isoxazole-based derivatives from Baylis–Hillman chemistry: assessment of preliminary hypolipidemic activity
  作者：A Patra、S Batra、A.P Bhaduri、A Khanna、R Chander、M Dikshit

  DOI：10.1016/s0968-0896(03)00105-6

  日期：2003.5

  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.
• 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.