ethyl (E)-2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate | 1256293-17-0

• 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: ethyl (E)-2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate
• 英文别名: ethyl (2E)-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methylidene]hexanoate
• CAS: 1256293-17-0
• 化学式: C₂₀H₃₈O₅Si
• 分子量: 386.604
• InChiKey: CDUNSBSULZQRMA-FYPAKXHLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.82
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl 2-(diisopropoxyphosphoryl)-6-(tert-butyldimethylsilyloxy)hexanoate 、 L-甘油醛缩丙酮 在 potassium tert-butylate 作用下， 以 乙二醇二甲醚 为溶剂， 反应 5.75h， 生成 ethyl (E)-2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate 、 ethyl (Z)-2-(4''-(tert-butyldimethylsilyloxy)butyl)-3-((R)-2',2'-dimethyl-1',3'-dioxolan-4'-yl)-acrylate
  参考文献：
  名称：

  Synthesis of a Functionalized 7,6-Bicyclic Spiroimine Ring Fragment of the Spirolides

  摘要：

  The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.

  DOI：

  10.1021/ol102525w

文献信息

• Synthesis of a Functionalized 7,6-Bicyclic Spiroimine Ring Fragment of the Spirolides
  作者：Stéphanie M. Guéret、Daniel P. Furkert、Margaret A. Brimble

  DOI：10.1021/ol102525w

  日期：2010.11.19

  The asymmetric synthesis of a functionalized 7,6-spiroimine related to the spirolides is described. Intermolecular Diels-Alder cycloaddition of a chiral trisubstituted dienophile and Danishefsky's diene enabled simultaneous installation of the C7 and C29 stereocenters. Further transformations and late-stage aza-Wittig cyclization afforded the spiroimine in good yield. During this study, an unprecedented 14-membered dialdimine was also obtained.