(-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-carboxymethylbicyclo[2.2.1]heptane | 372955-39-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-carboxymethylbicyclo[2.2.1]heptane
• 英文别名: (1S,2S,4R)-2-carboxymethyl-2-hydroxy-7,7-dimethyl-1-vinylbicyclo[2.2.1]heptane；2-[(1S,2S,4R)-1-ethenyl-2-hydroxy-7,7-dimethyl-2-bicyclo[2.2.1]heptanyl]acetic acid
• CAS: 372955-39-0
• 化学式: C₁₃H₂₀O₃
• 分子量: 224.3
• InChiKey: XHHLHBOEIZDWSN-WQAKAFBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-carboxymethylbicyclo[2.2.1]heptane 在 草酰氯 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 1.0h， 以37%的产率得到(-)-(1S,4R)-1-vinyl-7,7-dimethylbicyclo[2.2.1]heptane-2-spiro-2'-(4'-oxooxetane)
  参考文献：
  名称：

  摘要：

  Reactions were studied of (-)-(1S,4R)-1-vinyl-7,7-dimethylbicyclo[2.2.1]heptan-2-one with ethyl acetate lithium derivative, potassium acetylide, ozone, with a system OsO4-N-methylmorpholine N-oxide, and some subsequent transformations of the products obtained.

  DOI：

  10.1023/a:1013180012045
• 作为产物：
  描述：

  (-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-ethoxycarbonylmethylbicyclo[2.2.1]heptane 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以95%的产率得到(-)-(1S,2S,4R)-1-vinyl-2-hydroxy-7,7-dimethyl-2-carboxymethylbicyclo[2.2.1]heptane
  参考文献：
  名称：

  摘要：

  Reactions were studied of (-)-(1S,4R)-1-vinyl-7,7-dimethylbicyclo[2.2.1]heptan-2-one with ethyl acetate lithium derivative, potassium acetylide, ozone, with a system OsO4-N-methylmorpholine N-oxide, and some subsequent transformations of the products obtained.

  DOI：

  10.1023/a:1013180012045

文献信息

• ——
  作者：N. S. Vostrikov、A. V. Abutkov、L. V. Spirikhin、A. A. Fatykhov、M. S. Miftahov

  DOI：10.1023/a:1011360828286

  日期：——

  The Reformatsky reaction of bornanic enone (10-nor-1-vinylcamphor) with ethyl iodoacetate followed by iodocyclization afforded tricyclic iodolactone. Fragmentation of the latter initiated by HgO-I-2 gave rise to bicyclic iodoxolactone. Attempts to perform cyclization of this iodoxolactone analogously to intramolecular alkylation of CH-acids with halogen-containing electrophiles failed.