Methyl 4-hex-5-en-3-ylbenzoate | 102152-68-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Methyl 4-hex-5-en-3-ylbenzoate
• CAS: 102152-68-1
• 化学式: C₁₄H₁₈O₂
• 分子量: 218.296
• InChiKey: OASLBFGQIQOFJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Methyl 4-hex-5-en-3-ylbenzoate 在 ruthenium(IV) oxide 、 sodium periodate 作用下， 以 水 为溶剂， 以77%的产率得到3-(p-carbmethoxyphenyl)valeric acid
  参考文献：
  名称：

  Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin

  摘要：

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.

  DOI：

  10.1021/jm00156a026
• 作为产物：
  描述：

  4-(对羧基苯基)-1-己烯 、 甲醇 生成 Methyl 4-hex-5-en-3-ylbenzoate
  参考文献：
  名称：

  DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;SIROTNAK, FRANCIS M.

  摘要：

  DOI：

文献信息

• DEGRAW, JOSEPH I.;CHRISTIE, PAMELA H.;SIROTNAK, FRANCIS M.
  作者：DEGRAW, JOSEPH I.、CHRISTIE, PAMELA H.、SIROTNAK, FRANCIS M.

  DOI：——

  日期：——
• Synthesis and biological activity of resolved carbon-10 diastereomers of 10-methyl- and 10-ethyl-10-deazaminopterin
  作者：J. I. DeGraw、P. H. Christie、H. Tagawa、R. L. Kisliuk、Y. Gaumont、F. A. Schmid、F. M. Sirotnak

  DOI：10.1021/jm00156a026

  日期：1986.6

  Synthesis and evaluation of the antitumor drugs 10-methyl- and 10-ethyl-10-deazaminopterin (15a,b) were previously reported for the diastereomeric mixtures, lacking resolution at the C-10 position. In order to assess biological properties of the individual diastereomers, the C-10 isomers of 4-amino-4-deoxy-10-methyl- and 10-ethyl-10-deazapteroic acids (13a,b) were prepared by total synthesis. Coupling with L-glutamate afforded the appropriate diastereomers of the title compounds. Biochemical, transport, and cell growth inhibitory properties in L1210 cells and folate-dependent bacteria were measured. Differences were generally less than 2-fold between diastereomeric pairs, but a factor of 3 was noted for d,L-15b vs. l,L-15b in inhibition of DHFR from L1210 cells and in cytotoxicity toward L1210 cells. An in vivo comparison of the isomers of 15b with racemic compound against L1210 in mice did not show a significant efficacy difference (ILS) among the compounds. However, d,L-15b showed an acute toxicity about 2.5 times that of l,L-15b.