3-methyl-5,5-dimethoxy-pent-(2E)-enyl methyl carbonate | 1197011-18-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机碳酸及其衍生物
• 英文名称: 3-methyl-5,5-dimethoxy-pent-(2E)-enyl methyl carbonate
• 英文别名: [(E)-5,5-dimethoxy-3-methylpent-2-enyl] methyl carbonate
• CAS: 1197011-18-9
• 化学式: C₁₀H₁₈O₅
• 分子量: 218.25
• InChiKey: MIBBVNMJXAPGFD-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-dimethoxy-5-methyl-6-tributylstannanyl-4-(2-trimethylsilanyl-ethoxymethoxy)pyridine 、 3-methyl-5,5-dimethoxy-pent-(2E)-enyl methyl carbonate 在 tris-(dibenzylideneacetone)dipalladium(0) 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 、
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044
• 作为产物：
  描述：

  (E)-5,5-dimethoxy-3-methyl-pent-2-en-1-ol 、 氯甲酸甲酯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 3.0h， 以60%的产率得到3-methyl-5,5-dimethoxy-pent-(2E)-enyl methyl carbonate
  参考文献：
  名称：

  Total synthesis of (+)-piericidin A1 and (−)-piericidin B1

  摘要：

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetasy.2009.07.044

文献信息

• Total synthesis of (+)-piericidin A1 and (−)-piericidin B1
  作者：Ryosuke Kikuchi、Mikio Fujii、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2009.07.044

  日期：2009.9

  The convergent syntheses of (+)-piericidin A(1) 1 and (-)-piericidin B-1 2 have been achieved based on classical Julia-Lythgoe olefination between 4-hydroxy-5,6-dimethoxy-3-methyl-2-[5-oxo-3-methyl-pent-(2E)-enyl]-pyridine 3 corresponding to the left half of the final molecule, and chiral phenyl sulfones, (4R,5R)-2,4,6-trimethyl-5-methoxy-1-phenylsulfonyl-octa-(2E,6E)-diene 20 and (4R,5R)-5-tert-butyldimethylsiloxy-2,4,6-trimethyl-1-phenylsulfonyl-octa-(2E,6E)-diene 33, corresponding to the right halves. The construction of the two stereogenic centers in the right half of piericidins was achieved based on lipase-catalyzed hydrolysis of methyl (2,3)-anti-3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (+/-)-22. (C) 2009 Published by Elsevier Ltd.