ethyl 4-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-ethylenebutanoate | 1202183-64-9

• 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 4-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-ethylenebutanoate
• 英文别名: ethyl 4-[(4S,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]-4-hydroxy-2-methylidenebutanoate
• CAS: 1202183-64-9
• 化学式: C₁₄H₂₂O₅
• 分子量: 270.326
• InChiKey: LRTPWYWOCBWFAF-SAIIYOCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 4-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-ethylenebutanoate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以72%的产率得到(3aR,7aS)-ethyl 7-hydroxy-2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxole-5-carboxylate
  参考文献：
  名称：

  A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis

  摘要：

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.111
• 作为产物：
  描述：

  替格瑞洛杂质128 、 2-溴甲基丙烯酸乙酯 在 氯化铵 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到ethyl 4-((4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-4-hydroxy-2-ethylenebutanoate
  参考文献：
  名称：

  A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis

  摘要：

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.111

文献信息

• A concise route to (−)-shikimic acid and (−)-5-epi-shikimic acid, and their enantiomers via Barbier reaction and ring-closing metathesis
  作者：Pavan K. Kancharla、Venkata Ramana Doddi、Hariprasad Kokatla、Yashwant D. Vankar

  DOI：10.1016/j.tetlet.2009.09.111

  日期：2009.12

  A simple route for the synthesis of naturally occurring (-)-shikimic acid, (-)-5-epi-shikimic acid, and their enantiomers from D-ribose-derived enantiomeric aldehydes 8a and 8b by employing Barbier reaction and ring-closing metathesis as key steps has been developed. (C) 2009 Elsevier Ltd. All rights reserved.