4-allyl-2,2-dimethyl-5-(4-methyl-pent-3-enyl)-[1,3]dioxolane | 1301247-91-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-allyl-2,2-dimethyl-5-(4-methyl-pent-3-enyl)-[1,3]dioxolane
• 英文别名: (4S,5R)-2,2-dimethyl-4-(4-methylpent-3-enyl)-5-prop-2-enyl-1,3-dioxolane
• CAS: 1301247-91-5
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: VUIUNAIJIVKGMA-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(tert-butyl-diphenyl-silanyloxy)-6-methyl-hept-5-en-2-ol 在 4-二甲氨基吡啶 、 lithium tetrafluoroborate 、 四丙基高钌酸铵 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 水 、 N-甲基吗啉氧化物 、 N,N-二异丙基乙胺 、 (+)-B-methoxydiisocamphenylborane 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 4-allyl-2,2-dimethyl-5-(4-methyl-pent-3-enyl)-[1,3]dioxolane
  参考文献：
  名称：

  Synthesis of the Purported ent-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation

  摘要：

  The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the "desired" compound that does not spectroscopically correlate to the initially described natural product.

  DOI：

  10.1021/jo200332d

文献信息

• Synthesis of the Purported <i>ent</i>-Pochonin J Structure Featuring a Stereoselective Oxocarbenium Allylation
  作者：Dionicio Martinez-Solorio、Kenneth A. Belmore、Michael P. Jennings

  DOI：10.1021/jo200332d

  日期：2011.5.20

  The synthesis of the alleged natural product pochonin J is presented. Key steps of this convergent synthesis include a chemoselective Wacker oxidation, and an Evans' anti-reduction of the resulting ketone. Upon ozonolysis, this intermediate undergoes a 6-exo-trig cyclization to give a hemiketal intermediate, the key oxocarbenium precursor. The construction of the alpha-C-glycoside subunit is highlighted by a mismatched oxocarbenium cation formation/allylation sequence. An olefin metathesis afforded the 14-membered macrolactone, and final oxidation provided the "desired" compound that does not spectroscopically correlate to the initially described natural product.