4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-3-(2-ethoxy-2-oxoethyl)-D-arabino-hex-1-enitol | 123827-13-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-3-(2-ethoxy-2-oxoethyl)-D-arabino-hex-1-enitol
• 英文别名: ethyl 2-[(2R,3S,4R)-3-acetyloxy-2-(acetyloxymethyl)-3,4-dihydro-2H-pyran-4-yl]acetate
• CAS: 123827-13-4
• 化学式: C₁₄H₂₀O₇
• 分子量: 300.309
• InChiKey: UBDBKNPIGDHKNT-SCRDCRAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

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 palladium on activated charcoal 4-二甲氨基吡啶 、 偶氮二异丁腈 、 三甲基溴硅烷 、 硫酸 、 氢气 、 三正丁基氢锡 作用下， 以 吡啶 、 溶剂黄146 、 苯 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 反应 35.0h， 生成 4,6-di-O-acetyl-1,5-anhydro-2,3-dideoxy-3-(2-ethoxy-2-oxoethyl)-D-arabino-hex-1-enitol
  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：——