2-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylic acid methyl ester | 627882-17-1

• 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-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylic acid methyl ester
• 英文别名: Methyl 2-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazol-4-yl]-hydroxymethyl]prop-2-enoate
• CAS: 627882-17-1
• 化学式: C₁₅H₁₄ClNO₄
• 分子量: 307.733
• InChiKey: RZSJRDMCCURCEU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylic acid methyl ester 在 吡啶 、 三乙烯二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4-acetyl-3-[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]-2-methylene-5-oxohexanoic acid methyl ester
  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-chloro-N-hydroxybenzimidoyl chloride 在 三乙烯二胺 、 lithium aluminium tetrahydride 、 sodium methylate 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 77.5h， 生成 2-{[3-(2-chlorophenyl)-5-methylisoxazol-4-yl]hydroxymethyl}acrylic acid methyl ester
  参考文献：
  名称：

  高度取代的异恶唑：取代的 4-异恶唑甲醛的 Baylis-Hillman 反应和尝试环化为异恶唑环化衍生物

  摘要：

  为了了解甲酰基的位置对异恶唑甲醛中 Baylis-Hillman 反应效率的影响，描述了取代的 4-异恶唑-甲醛获得高度取代的异恶唑的反应。还描述了从这些涉及 SN R'-SN Ar 取代策略的 Baylis-Hillman 加合物中获得异恶唑环化衍生物的尝试。

  DOI：

  10.1055/s-2003-40204

文献信息

• 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
• 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。