[(3S,4S,5R,6S)-5-(methoxymethoxy)-4,6-dimethyl-1-oxooctan-3-yl] (E)-3-phenylprop-2-enoate | 1063968-06-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: [(3S,4S,5R,6S)-5-(methoxymethoxy)-4,6-dimethyl-1-oxooctan-3-yl] (E)-3-phenylprop-2-enoate
• CAS: 1063968-06-8
• 化学式: C₂₁H₃₀O₅
• 分子量: 362.466
• InChiKey: WROQYHRYRLZULL-RISZGHKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  [(3S,4S,5R,6S)-5-(methoxymethoxy)-4,6-dimethyl-1-oxooctan-3-yl] (E)-3-phenylprop-2-enoate 、 碘甲烷 在 chromium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 12.0h， 以83%的产率得到(1E,4S,5R,6R,7S)-1-iodo-5,7-dimethyl-4-[(2E)-3-phenylacryloxy]-6-methoxymethoxy-oct-1-ene
  参考文献：
  名称：

  Stereoselective synthesis of basiliskamides A and B via Prins cyclisation

  摘要：

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.024
• 作为产物：
  描述：

  [(4S,5S,6R,7S)-6-(methoxymethoxy)-5,7-dimethylnon-1-en-4-yl] (E)-3-phenylprop-2-enoate 在 甲基磺酰胺 、 sodium periodate 作用下， 以 水 、 叔丁醇 、 四氢呋喃 为溶剂， 反应 26.0h， 以72%的产率得到[(3S,4S,5R,6S)-5-(methoxymethoxy)-4,6-dimethyl-1-oxooctan-3-yl] (E)-3-phenylprop-2-enoate
  参考文献：
  名称：

  Stereoselective synthesis of basiliskamides A and B via Prins cyclisation

  摘要：

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.

  DOI：

  10.1016/j.tetlet.2008.07.024

文献信息

• Stereoselective synthesis of basiliskamides A and B via Prins cyclisation
  作者：J.S. Yadav、P. Purushothama Rao、M. Sridhar Reddy、A.R. Prasad

  DOI：10.1016/j.tetlet.2008.07.024

  日期：2008.9

  A stereoselective and convergent approach to basiliskamides A and B is achieved through our recently developed strategy for the construction of polyketide precursors via Prins cyclisation. The approach mainly relies upon reductive opening of 1-iodomethyl cyclic ethers, Mitsunobu inversion, Takai olefination and Stille coupling along with Prins cyclisation. (c) 2008 Elsevier Ltd. All Fights reserved.