[(2R)-1-[tert-butyl(dimethyl)silyl]oxypent-4-en-2-yl] prop-2-enoate | 909570-86-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: [(2R)-1-[tert-butyl(dimethyl)silyl]oxypent-4-en-2-yl] prop-2-enoate
• CAS: 909570-86-1
• 化学式: C₁₄H₂₆O₃Si
• 分子量: 270.444
• InChiKey: DSXBFSGVKVSJGY-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.68
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [(2R)-1-[tert-butyl(dimethyl)silyl]oxypent-4-en-2-yl] prop-2-enoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 草酰氯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 27.0h， 生成 (R)-6-Oxo-3,6-dihydro-2H-pyran-2-carbaldehyde
  参考文献：
  名称：

  Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

  摘要：

  A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.054
• 作为产物：
  描述：

  (R)-t-叔丁基二甲基硅基缩水甘油醚 在 TEA 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(2R)-1-[tert-butyl(dimethyl)silyl]oxypent-4-en-2-yl] prop-2-enoate
  参考文献：
  名称：

  Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis

  摘要：

  A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.06.054

文献信息

• Total synthesis of (R)-(+)-goniothalamin and (R)-(+)-goniothalamin oxide: first application of the sulfoxide-modified Julia olefination in total synthesis
  作者：Jiří Pospíšil、István E. Markó

  DOI：10.1016/j.tetlet.2006.06.054

  日期：2006.8

  A short and efficient synthesis of (R)-(+)-goniothalamin 1 and (R)-(+)-goniothalamin oxide 2 is described. During this approach, the sulfoxide-modified Julia olefination was used as a key step to connect aldehyde 5 to sulfoxide 6. The desired styryl-containing adduct is obtained in good yield and with excellent E/Z selectivity. (c) 2006 Elsevier Ltd. All rights reserved.