(2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methylhept-5-en-2-ol | 338387-80-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methylhept-5-en-2-ol
• CAS: 338387-80-7
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: MANKGINXPINMDG-YPMHNXCESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 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：

  (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methylhept-5-en-2-ol 在 4-甲基苯磺酸吡啶 作用下， 以 甲醇 为溶剂， 以90%的产率得到(2R,3S)-3,7-dimethyl-6-octene-1,2,3-triol
  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
• 作为产物：
  描述：

  5-溴-2-甲基-2-戊烯 在 草酰氯 、 TEA 、 四氯化锡 、 magnesium 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 (2S)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methylhept-5-en-2-ol
  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

文献信息

• Synthesis of the Major Oxepane Segment of Zoapatanol
  作者：Jhillu S. Yadav、Uttam Dash、Nagesh Guguloth、Debendra K. Mohapatra

  DOI：10.1002/hlca.201200364

  日期：2013.4

  A linear synthesis of the major oxepane fragment of zoapatanol, showing the induction of uterine contractions, and cervical dilation and uterine bleeding (by the concentrated zoapatle tea) in early human pregnancy, isolated from the leaves of Mexican zoapatle plant Montanoa tomentosa, is described from known intermediate involving Sharpless asymmetric epoxidation, bis‐epoxide opening reaction with

  zoapatanol的主要氧杂环庚烷片段的人类早期妊娠的线性合成，显示子宫收缩的诱导，和子宫颈扩张和子宫出血（由浓zoapatle茶），来自墨西哥zoapatle植物的叶中分离Montanoa毛白杨，从描述已知中间涉及夏普勒斯不对称环氧化，用双-环氧化物开环反应科里 Chaykovsky试剂，闭环复分解反应，和霍纳尔沃兹沃思埃蒙斯作为关键步骤烯化反应。
• 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.