ethyl <2S-(2α,3β,6β)>-6-(bromomethyl)-3,6-dihydro-2-methoxy-2H-pyran-3-acetate | 123827-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: ethyl <2S-(2α,3β,6β)>-6-(bromomethyl)-3,6-dihydro-2-methoxy-2H-pyran-3-acetate
• 英文别名: ethyl 2-[(2S,3S,6S)-6-(bromomethyl)-2-methoxy-3,6-dihydro-2H-pyran-3-yl]acetate
• CAS: 123827-11-2
• 化学式: C₁₁H₁₇BrO₄
• 分子量: 293.158
• InChiKey: UKCWRVGVYAEWLS-YWVKMMECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,1aR,2S,3aR,6R,7aS,7bS)-2-Methoxy-6-phenyl-hexahydro-3,5,7-trioxa-cyclopropa[a]naphthalene-1-carboxylic acid ethyl ester 在 N-溴代丁二酰亚胺(NBS) 、 magnesium(II) perchlorate 、 N-甲基咔唑 、 barium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 18.0h， 生成 ethyl <2S-(2α,3β,6β)>-6-(bromomethyl)-3,6-dihydro-2-methoxy-2H-pyran-3-acetate
  参考文献：
  名称：

  Use of radical ring opening for introduction of alkyl and substituted alkyl groups with stereochemical control: a synthetic application of cyclopropylcarbinyl radicals

  摘要：

  Cyclopropylcarbinols 2a and 2b (see Scheme I), which are accessible by a number of routes, can be converted into the corresponding radicals 3a and 3b, respectively. These radicals undergo peripheral ring-opening of the cyclopropyl substructure to afford substituted cycloalkenes 4a and 4b. The whole sequence represents a general method for attaching alkyl, and substituted alkyl, groups to an existing cyclic structure, and it can often be carried out with predictable stereo- and regiochemical control. Reaction conditions for the ring-opening depend on the substitution pattern of the cyclopropane: where the non-bridgehead carbon of the cyclopropane carries a strongly electron-withdrawing group, the ring-opening can be done at the reflux temperature of benzene. However, in the absence of such electron-withdrawing groups, a low temperature is best used in order to suppress ring expansion. Various methods that accommodate these requirements are available for generating the radicals.

  DOI：

  10.1021/jo00012a009

文献信息

• CLIVE, DERRICK L. J.;DAIGNEAULT, SYLVAIN, J. CHEM. SOC. CHEM. COMMUN.,(1989) N, C. 332-335
  作者：CLIVE, DERRICK L. J.、DAIGNEAULT, SYLVAIN

  DOI：——

  日期：——