methyl 2-((R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyloxy)acrylate | 615558-01-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-((R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyloxy)acrylate
• 英文别名: methyl 2-[(R)-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-[(4R,5R)-5-ethenyl-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]prop-2-enoate
• CAS: 615558-01-5
• 化学式: C₁₇H₂₆O₇
• 分子量: 342.389
• InChiKey: HYTIWPMAJDXOHM-AAVRWANBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-((R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyloxy)acrylate 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以84%的产率得到methyl (3aS,4R,7aR)-4-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,7a-dihydro-4H-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
  参考文献：
  名称：

  Ring-closing metathesis of α-ester-substituted enol ethers: application to the shortest synthesis of KDO

  摘要：

  Ring-closing metathesis reactions of alpha-ester-substituted enol ethers are described. In the case of unsubstituted terminal olefins, isomerization prior to cyclization was observed as an undesired side reaction, which could not be completely inhibited. Furthermore, this methodology was applied to a formal synthesis of KDO, which now represents the shortest synthetic pathway to KDO and its deoxy analogue. Interestingly, in this route olefin isomerization was not observed, presumably due to the increased steric environment of the double bond. Finally, an efficient two-step conversion to transform an alcohol into an alpha-alkoxy acrylate is also described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00819-6
• 作为产物：
  描述：

  (2R,3R,4R,5R)-1,2:4,5-di-O-isopropylidene-hept-6-ene-1,2,3,4,5-pentol 在 sodium hydride 、 sodium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 35.0h， 生成 methyl 2-((R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-[(4S,5R)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl]methyloxy)acrylate
  参考文献：
  名称：

  Ring-closing metathesis of α-ester-substituted enol ethers: application to the shortest synthesis of KDO

  摘要：

  Ring-closing metathesis reactions of alpha-ester-substituted enol ethers are described. In the case of unsubstituted terminal olefins, isomerization prior to cyclization was observed as an undesired side reaction, which could not be completely inhibited. Furthermore, this methodology was applied to a formal synthesis of KDO, which now represents the shortest synthetic pathway to KDO and its deoxy analogue. Interestingly, in this route olefin isomerization was not observed, presumably due to the increased steric environment of the double bond. Finally, an efficient two-step conversion to transform an alcohol into an alpha-alkoxy acrylate is also described. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00819-6

文献信息

• Ring-closing metathesis of α-ester-substituted enol ethers: application to the shortest synthesis of KDO
  作者：Koen F.W Hekking、Floris L van Delft、Floris P.J.T Rutjes

  DOI：10.1016/s0040-4020(03)00819-6

  日期：2003.8

  Ring-closing metathesis reactions of alpha-ester-substituted enol ethers are described. In the case of unsubstituted terminal olefins, isomerization prior to cyclization was observed as an undesired side reaction, which could not be completely inhibited. Furthermore, this methodology was applied to a formal synthesis of KDO, which now represents the shortest synthetic pathway to KDO and its deoxy analogue. Interestingly, in this route olefin isomerization was not observed, presumably due to the increased steric environment of the double bond. Finally, an efficient two-step conversion to transform an alcohol into an alpha-alkoxy acrylate is also described. (C) 2003 Elsevier Ltd. All rights reserved.