4-acetyl-2-methylene-5-oxo-3-phenylhexanoic acid methyl ester | 849777-68-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-acetyl-2-methylene-5-oxo-3-phenylhexanoic acid methyl ester
• 英文别名: methyl 4-acetyl-2-methylene-5-oxo-3-phenylhexanoate；Methyl 4-acetyl-2-methylidene-5-oxo-3-phenylhexanoate；methyl 4-acetyl-2-methylidene-5-oxo-3-phenylhexanoate
• CAS: 849777-68-0
• 化学式: C₁₆H₁₈O₄
• 分子量: 274.317
• InChiKey: MURDAKPWVKDUMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetyl-2-methylene-5-oxo-3-phenylhexanoic acid methyl ester 在 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成
  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-(羟基苯基甲基)-丙烯酸甲酯 在 吡啶 、 三乙烯二胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.5h， 生成 4-acetyl-2-methylene-5-oxo-3-phenylhexanoic 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

文献信息

• S_N2’ versus S_N2 Reactivity: Control of Regioselectivity in Conversions of Baylis-Hillman Adducts
  作者：Mahiuddin Baidya、Grygoriy Y. Remennikov、Peter Mayer、Herbert Mayr

  DOI：10.1002/chem.200902487

  日期：2010.1.25

  is used, a second SN2’ reaction converts 8 into their thermodynamically more stable allyl isomers 9. The second‐order rate constants for the reactions of 6 with carbanions have been determined photometrically in DMSO. With these rate constants and the previously reported nucleophile‐specific parameters N and s for the stabilized carbanions, the correlation log k (20 °C)=s(N + E) allowed us to calculate

  TiCl 4诱导的α，β-不饱和羰基化合物与醛的Baylis-Hillman反应产生（Z）-2-（氯甲基）乙烯基羰基化合物5，该化合物与1,4-二氮杂双环[2.2.2]辛烷（DABCO ），奎尼丁和吡啶，得到烯丙基铵离子6。将它们与少于一当量的稳定化碳负离子的钾盐（例如丙二酸酯）结合，可在动力学控制的条件下（S N 2'反应）生成亚甲基衍生物8。当使用多于一个当量的碳负离子时，第二个S N 2'反应将8转化为其热力学更稳定的烯丙基异构体9。已在DMSO中以光度法确定了6与碳负离子反应的二级速率常数。利用这些速率常数和先前报道的稳定化碳负离子的亲核试剂特定参数N和s，相关性对数k（20°C）= s（N + E）使我们能够计算出烯丙基铵离子6的亲电参数E（ -19 < E <−18）。动力学数据表明，S N 2'反应通过加速率消除加成消除机理进行。
• P₂O₅-Promoted Efficient and Diastereoselective Synthesis of Substituted 5-Methylene-dihydropyran-2,6-diones and 3-Methylene-3,4-dihydropyran-2-ones
  作者：Vijay Singh、Sudharshan Madapa、Sanjay Batra

  DOI：10.1080/00397910802028879

  日期：2008.6.20

  A simple, efficient, and diastereoselective synthesis of 5-methylene-dihydropyran-2,6-diones and 3-methylene-3,4-dihydropyran-2-ones from substrates afforded by the S(N)(2) reaction between the acetyl derivatives of the Baylis-Hillman adducts and methylacetoacetate or acetylacetone or benzoyl acetone via saponification followed by P(2)O(5)-mediated cyclization is described.
• 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.