2-exo-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 2-exo-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol
• 英文别名: (1S,2S,4S)-2-methyl-7-oxabicyclo[2.2.1]hept-5-en-2-ol
• 化学式: C₇H₁₀O₂
• 分子量: 126.155
• InChiKey: KEBUMDDAUPMFRZ-VQVTYTSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-exo-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol 在 sodium hydride 作用下， 以 乙醚 为溶剂， 反应 4.25h， 生成 (1S*,2R*,5S*)-5-benzyloxy-2-n-butyl-5-methyl-cyclohex-3-en-1-ol
  参考文献：
  名称：

  有机锂试剂对7-氧杂降冰片烯的开环Sn2'反应。取代的环己二醇的区域和立体定向合成

  摘要：

  7-氧杂双环[2.2.1]庚-5-烯-2-醇与有机锂试剂的亲核Sn2'桥开口以区域和立体特异性方式发生，以产生6-取代的环己-4-烯-1,3 -二醇，无论在C-2处的立体化学如何。要完全控制该过程，必须使用游离的醇功能。该方法用于制备光学纯的环己烯衍生物（+）-（1S，3S，6R）-6-正丁基-3-甲基-环己-4-en-1,3-二醇（5b），模型系统。

  DOI：

  10.1016/s0040-4020(01)81475-7
• 作为产物：
  描述：

  甲基碘化镁 、 7-oxabicyclo[2.2.1]hept-5-en-2-one 以 乙醚 为溶剂， 反应 0.25h， 以95%的产率得到2-exo-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-endo-ol
  参考文献：
  名称：

  Stereoselectivity of organometallic reagents addition to 7-oxabicyclo[2.2.1]hept-5-en-2-one

  摘要：

  DOI：

  10.1021/jo00278a032

文献信息

• Regio- and stereoselective electrophilic additions to and -2-hydroxy-2-methyl-7-oxabicyclo[2.2.1]hept-5-ene
  作者：Odón Arjona、Roberto Fernandez de la Pradilla、Rosa A. Pérez、Joaquín Plumet、Alma Viso

  DOI：10.1016/s0040-4039(00)96777-7

  日期：1987.1

  The regio- and stereoselectivity of electrophilic additions of PhSeCl and PhSCl to isomeric 2-hydroxy-2-methyl-7-oxabicyclo[2.2.1]hept-5-enes is highly dependent upon the relative stereochemistry of the substrate.

  PhSeCl和PhSCl对异构体2-羟基-2-甲基-7-氧杂双环[2.2.1]庚-5-烯的亲电加成的区域和立体选择性在很大程度上取决于底物的相对立体化学。
• Regio- and stereospecific synthesis of substituted cyclohexenediols from 7-oxabicyclo[2.2.1]hept-5-en-2-ols and organolithium reagents
  作者：Odón Arjona、Roberto Fernández de la Pradilla、Ernesto García、Angel Martin-Domenech、Joaquín Plumet

  DOI：10.1016/s0040-4039(01)93916-4

  日期：1989.1

  The bridge opening reactions of 7-oxabicyclo[2.2.1]hept-5-en-2-ols,4 and6 with organolithium reagents proceed with complete regio- and stereoselectivity to produce highly functionalized cyclohexene derivatives5 and7, respectively.

  7-氧杂双环[2.2.1]庚-5-烯-2-醇，4和6与有机锂试剂的桥开反应以完全的区域选择性和立体选择性进行，分别产生高度官能化的环己烯衍生物5和7。
• Stereoselectivity of the reaction between 7-oxabicyclo[2.2.1]hept-5-en-2-one and organocuprate reagents
  作者：Odón Arjona、Roberto Fernández de la Pradilla、Cristina Manzano、Sonia Pérez、Joaquín Plumet

  DOI：10.1016/s0040-4039(00)96776-5

  日期：1987.1

  Lithium organocuprates add with high stereoselectivity to the hindered face of the carbonyl group of 7-oxabicyclo[2.2.1]hept-5-en-2-one to yield the corresponding alcohols.

  有机铜酸锂以高的立体选择性加到7-氧杂双环[2.2.1]庚-5-烯-2-酮的羰基的受阻面上，得到相应的醇。
• Temperature-controlled synthesis of 4,7-dioxatricyclo[3.2.1.03,6]octane derivatives
  作者：Odon Arjona、Roberto Fernandez de la Pradilla、Joaquin Plumet、Alma Viso

  DOI：10.1021/jo00028a074

  日期：1992.1
• Sulfone Directed Alkylative Bridge Cleavage of Oxabicyclic Vinyl Sulfones with Organolithium Reagents
  作者：Odon Arjona、Alfonso de Dios、Roberto Fernandez de la Pradilla、Joaquin Plumet、Alma Viso

  DOI：10.1021/jo00093a024

  日期：1994.7

  An efficient regio- and stereocontrolled methodology for the alkylative bridge cleavage of oxabicyclic vinyl sulfones is described. A range of 7-oxabicyclo[2.2.1]heptenyl and 8-oxabicyclo[3.2.1]octenyl sulfones has been found to undergo an overall syn S(N)2' opening when treated with a wide variety of organolithium reagents and lithium aluminum hydride. In this manner, highly functionalized cyclohexenyl and cycloheptenyl sulfones, versatile synthetic intermediates, are now available in high yields. The complete stereoselectivity encountered in the exo conjugate addition may be explained by chelation of the organometallic reagent with the oxygen bridge and steric factors. Furthermore, less-strained substrates allow for complete control of the addition and elimination stages.