(R,E)-methyl 5-(tert-butyldimethylsilyloxy)-8-methyl-3-oxoundeca-8,10-dienoate | 1446794-88-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: (R,E)-methyl 5-(tert-butyldimethylsilyloxy)-8-methyl-3-oxoundeca-8,10-dienoate
• 英文别名: methyl (5R,8E)-5-[tert-butyl(dimethyl)silyl]oxy-8-methyl-3-oxoundeca-8,10-dienoate
• CAS: 1446794-88-2
• 化学式: C₁₉H₃₄O₄Si
• 分子量: 354.562
• InChiKey: DSSXWGIKAKLIOM-IUYQLWOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.81
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R,E)-methyl 5-(tert-butyldimethylsilyloxy)-8-methyl-3-oxoundeca-8,10-dienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以90%的产率得到(R,E)-methyl 5-hydroxy-8-methyl-3-oxoundeca-8,10-dienoate
  参考文献：
  名称：

  Stereoselective total synthesis of Ieodomycin A and B

  摘要：

  The stereoselective total synthesis of Ieodomycin A and B, bioactive secondary metabolites from marine sources with potent anti-microbial activity was achieved starting from commercially available geranial. The key steps involved in the synthetic sequence of Ieodomycin A and B are the Sharpless asymmetric epoxidation, the formation of a beta-ketoester, and the 1,3-anti reduction. The synthesis of C-3 epimer of Ieodomycin A and B was also accomplished in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.002
• 作为产物：
  描述：

  (3E)-4,8-二甲基壬-1,3,7-三烯 在 咪唑 、 titanium(IV) isopropylate 、 4-二甲氨基吡啶 、 sodium periodate 、 periodic acid dihydrate 、 tin(II) chloride dihdyrate 、 过氧化氢异丙苯 、 二异丁基氢化铝 、 D-(-)-酒石酸二异丙酯 、 间氯过氧苯甲酸 、 红铝 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 、 苯 为溶剂， 反应 23.83h， 生成 (R,E)-methyl 5-(tert-butyldimethylsilyloxy)-8-methyl-3-oxoundeca-8,10-dienoate
  参考文献：
  名称：

  Stereoselective total synthesis of Ieodomycin A and B

  摘要：

  The stereoselective total synthesis of Ieodomycin A and B, bioactive secondary metabolites from marine sources with potent anti-microbial activity was achieved starting from commercially available geranial. The key steps involved in the synthetic sequence of Ieodomycin A and B are the Sharpless asymmetric epoxidation, the formation of a beta-ketoester, and the 1,3-anti reduction. The synthesis of C-3 epimer of Ieodomycin A and B was also accomplished in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.05.002

文献信息

• Stereoselective total synthesis of Ieodomycin A and B
  作者：Emmadi Narender Reddy、Atmakur Krishnaiah、Tadikamalla Prabhakar Rao

  DOI：10.1016/j.tetasy.2013.05.002

  日期：2013.6

  The stereoselective total synthesis of Ieodomycin A and B, bioactive secondary metabolites from marine sources with potent anti-microbial activity was achieved starting from commercially available geranial. The key steps involved in the synthetic sequence of Ieodomycin A and B are the Sharpless asymmetric epoxidation, the formation of a beta-ketoester, and the 1,3-anti reduction. The synthesis of C-3 epimer of Ieodomycin A and B was also accomplished in good yields. (C) 2013 Elsevier Ltd. All rights reserved.