3-hydroxy-2-methylene-oct-4-enoic acid methyl ester | 112247-20-8

• 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: 3-hydroxy-2-methylene-oct-4-enoic acid methyl ester
• 英文别名: methyl (E)-3-hydroxy-2-methylideneoct-4-enoate
• CAS: 112247-20-8
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: BZJXXRIEFXXBDY-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三乙基硅基三氟甲磺酸酯 、 3-hydroxy-2-methylene-oct-4-enoic acid methyl ester 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以94%的产率得到2-methylene-3-(triethylsilanyloxy)-oct-4-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Cytoprotective Properties of Dykellic Acid

  摘要：

  Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these, compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly Suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.

  DOI：

  10.1021/jm801169s
• 作为产物：
  描述：

  2-已烯醛 、 丙烯酸甲酯（MA） 在 三乙烯二胺 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以17%的产率得到3-hydroxy-2-methylene-oct-4-enoic acid methyl ester
  参考文献：
  名称：

  Total Synthesis and Cytoprotective Properties of Dykellic Acid

  摘要：

  Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these, compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly Suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.

  DOI：

  10.1021/jm801169s

文献信息

• Palladium-Catalyzed Regio- and Enantioselective Allylic Alkylation of Bis Allylic Carbonates Derived from Morita−Baylis−Hillman Adducts
  作者：Barry M. Trost、Megan K. Brennan

  DOI：10.1021/ol701585b

  日期：2007.9.1

  Morita-Baylis-Hillman diene adducts are used as substrates in the palladium-catalyzed asymmetric allylic alkylation reaction with oxygen and carbon nucleophiles in good regio- and enantioselectivity.

  Morita-Baylis-Hillman二烯加合物用作钯与氧和碳亲核试剂的区域和对映体选择性良好的钯催化不对称烯丙基烷基化反应的底物。
• Generation of [.alpha.-(alkoxycarbonyl)vinyl]aluminum and aluminum allenolates by the hydroalumination of .alpha.,.beta.-acetylenic carbonyl compounds and their reaction with carbonyl compounds
  作者：Tetsuo Tsuda、Tsutomu Yoshida、Takeo Saegusa

  DOI：10.1021/jo00240a020

  日期：1988.3
• TSUDA, TETSUO;YOSHIDA, TSUTOMU;SAEGUSA, TAKEO, J. ORG. CHEM., 53,(1988) N 5, 1037-1040
  作者：TSUDA, TETSUO、YOSHIDA, TSUTOMU、SAEGUSA, TAKEO

  DOI：——

  日期：——
• Total Synthesis and Cytoprotective Properties of Dykellic Acid
  作者：Christina M. Thompson、Catherine A. Quinn、Paul J. Hergenrother

  DOI：10.1021/jm801169s

  日期：2009.1.8

  Small molecule inhibitors of apoptosis hold considerable promise for the treatment of a host of diseases, including neurodegeneration, myocardial infarction, and stroke. Many compounds that delay or prevent apoptotic death either reduce the amount of cellular reactive oxygen species (ROS) or are direct inhibitors of caspases. With the goal of using small molecules to identify novel antiapoptotic targets, we have investigated the cytoprotective activity of the natural product dykellic acid. Described herein is the first total synthesis of dykellic acid, the synthesis of several dykellic acid derivatives, and the evaluation of these, compounds in assays related to cell death. We have found that dykellic acid protects cells from death as induced by etoposide and rotenone. Further experiments strongly Suggest that dykellic acid does not scavenge ROS or directly inhibit caspase enzymes, and analysis of synthetic derivatives establishes key functional groups of the molecule that are essential for its cytoprotective activity.