1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methylhex-4-en-1-ol | 338387-75-0

• 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: 1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methylhex-4-en-1-ol
• CAS: 338387-75-0
• 化学式: C₁₂H₂₂O₃
• 分子量: 214.305
• InChiKey: HNPGRXFJJOHHTM-RRKGBCIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methylhex-4-en-1-ol 在 草酰氯 、 TEA 、 水 、 四氯化锡 、 copper(II) sulfate 、 二甲基亚砜 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 threo-3,7-dimethyl-6-octene-1,2,3-triol
  参考文献：
  名称：

  Diastereocontrol in the Reaction of (R)-2,2-Dimethyl-4-acyl-1,3-dioxolanes with Alkylmetals: A Facile Entry to Enantiopure Terpenetriols

  摘要：

  DOI：

  10.3987/com-00-s(i)76
• 作为产物：
  描述：

  magnesium,2-methylpent-2-ene,bromide 、 (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 以 四氢呋喃 为溶剂， 以91%的产率得到1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-5-methylhex-4-en-1-ol
  参考文献：
  名称：

  Enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol: a Colorado potato beetle pheromone

  摘要：

  The recent identification of a male-produced aggregation pheromone [(S)-3,7-dimethyl-2-oxo-6-octene1,3-diol, (S)-CPB] offers a new tool for Colorado potato beetle (CPB) management. We developed a novel synthetic approach to produce CPB pheromone in seven steps and 46.54% overall yield. Grignard reaction, oxidation, and stereoselective methylation using organometallic reagent are the key steps in the commercially viable total synthesis, generating CPB pheromone in 98.6% enantiomeric purity and gram quantity. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2008.10.092

文献信息

• Diastereocontrol in the Reaction of (R)-2,2-Dimethyl-4-acyl-1,3-dioxolanes with Alkylmetals: A Facile Entry to Enantiopure Terpenetriols
  作者：Takeshi Nakai、Hisashi Mikoshiba、Koichi Mikami

  DOI：10.3987/com-00-s(i)76

  日期：——
• Enantioselective synthesis of (S)-3,7-dimethyl-2-oxo-6-octene-1,3-diol: a Colorado potato beetle pheromone
  作者：Bathini Nagendra Babu、Kamlesh R. Chauhan

  DOI：10.1016/j.tetlet.2008.10.092

  日期：2009.1

  The recent identification of a male-produced aggregation pheromone [(S)-3,7-dimethyl-2-oxo-6-octene1,3-diol, (S)-CPB] offers a new tool for Colorado potato beetle (CPB) management. We developed a novel synthetic approach to produce CPB pheromone in seven steps and 46.54% overall yield. Grignard reaction, oxidation, and stereoselective methylation using organometallic reagent are the key steps in the commercially viable total synthesis, generating CPB pheromone in 98.6% enantiomeric purity and gram quantity. Published by Elsevier Ltd.