(E)-14-iodotetradeca-13-en-3,5-diyn-1-ol

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: (E)-14-iodotetradeca-13-en-3,5-diyn-1-ol
• 英文别名: placotylene A；(E)-14-iodotetradec-13-en-3,5-diyn-1-ol
• 化学式: C₁₄H₁₉IO
• 分子量: 330.209
• InChiKey: USDJMPOEDBMDSE-ACCUITESSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  16.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  乙烯利 、 (E)-14-iodotetradeca-13-en-3,5-diyn-1-ol 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.25h， 以75%的产率得到
  参考文献：
  名称：

  Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A)

  摘要：

  The convergent total synthesis of the marine natural product phosphoiodyn A, a nanomolar agonist of human peroxisome proliferator-activated receptor delta (hPPARd), was achieved in five steps total from commercially available and inexpensive starting materials. The synthesis relies on the unprecedented regioselective hydrozirconation of a terminal acetylene in the presence of a conjugated 1,3-diyne and on ammonolysis of a beta-chlorophosphonic acid monoester. The scheme also provides the newly isolated placotylene A, an inhibitor of bone marrow-derived macrophage (BMM) differentiation.

  DOI：

  10.1021/acs.orglett.5b02642
• 作为产物：
  描述：

  在 二异丁基氢化铝 、 Schwartz's reagent 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以84%的产率得到(E)-14-iodotetradeca-13-en-3,5-diyn-1-ol
  参考文献：
  名称：

  Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A)

  摘要：

  The convergent total synthesis of the marine natural product phosphoiodyn A, a nanomolar agonist of human peroxisome proliferator-activated receptor delta (hPPARd), was achieved in five steps total from commercially available and inexpensive starting materials. The synthesis relies on the unprecedented regioselective hydrozirconation of a terminal acetylene in the presence of a conjugated 1,3-diyne and on ammonolysis of a beta-chlorophosphonic acid monoester. The scheme also provides the newly isolated placotylene A, an inhibitor of bone marrow-derived macrophage (BMM) differentiation.

  DOI：

  10.1021/acs.orglett.5b02642

文献信息

• Five Easy Pieces. The Total Synthesis of Phosphoiodyn A (and Placotylene A)
  作者：David J. Galler、Kathlyn A. Parker

  DOI：10.1021/acs.orglett.5b02642

  日期：2015.11.20

  The convergent total synthesis of the marine natural product phosphoiodyn A, a nanomolar agonist of human peroxisome proliferator-activated receptor delta (hPPARd), was achieved in five steps total from commercially available and inexpensive starting materials. The synthesis relies on the unprecedented regioselective hydrozirconation of a terminal acetylene in the presence of a conjugated 1,3-diyne and on ammonolysis of a beta-chlorophosphonic acid monoester. The scheme also provides the newly isolated placotylene A, an inhibitor of bone marrow-derived macrophage (BMM) differentiation.