7-benzyloxy-2-methyleneheptane-1,5-diol | 953804-81-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7-benzyloxy-2-methyleneheptane-1,5-diol
• 英文别名: 2-Methylidene-7-phenylmethoxyheptane-1,5-diol；2-methylidene-7-phenylmethoxyheptane-1,5-diol
• CAS: 953804-81-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: ZWBDVLOXWUSEGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-benzyloxy-2-methyleneheptane-1,5-diol 在 palladium diacetate titanium(IV) isopropylate 、 4 A molecular sieve 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以85%的产率得到2-(2-(benzyloxy)ethyl)-5-methylenetetrahydro-2H-pyran
  参考文献：
  名称：

  A [3 + 3] Annelation Approach to (+)-Rhopaloic Acid B

  摘要：

  A general and enantiospecific [3 + 3] reaction toward functionalized pyrans is reported that has been employed in the first enantioselective synthesis of (+)-rhopaloic acid B.

  DOI：

  10.1021/ol701553j
• 作为产物：
  描述：

  2-(2-(苄氧基)乙基)环氧乙烷 、 2-甲基-2-丙烯-1-醇 在 正丁基锂 、 四甲基乙二胺 、 magnesium bromide 作用下， 以 乙醚 、 四氢呋喃 为溶剂， 反应 27.5h， 以74%的产率得到7-benzyloxy-2-methyleneheptane-1,5-diol
  参考文献：
  名称：

  A [3 + 3] Annelation Approach to (+)-Rhopaloic Acid B

  摘要：

  A general and enantiospecific [3 + 3] reaction toward functionalized pyrans is reported that has been employed in the first enantioselective synthesis of (+)-rhopaloic acid B.

  DOI：

  10.1021/ol701553j

文献信息

• Investigation of an Organomagnesium-Based [3 + 3] Annelation to Pyrans and Its Application in the Synthesis of Rhopaloic Acid A
  作者：Julien C. R. Brioche、Katharine M. Goodenough、David J. Whatrup、Joseph P. A. Harrity

  DOI：10.1021/jo702620e

  日期：2008.3.1

  [GRAPHICS]A stepwise [3 + 3] annelation reaction has been developed that allows access to pyrans from epoxides. This process involves the addition of an allylmagnesium reagent, itself readily prepared from methallyl alcohol, and a Pd-catalyzed cyclodehydration reaction. The potential of this process to be employed in natural product synthesis has been exemplified by its use in the preparation of rhopaloic acid A.
• A [3 + 3] Annelation Approach to (+)-Rhopaloic Acid B
  作者：Julien C. R. Brioche、Katharine M. Goodenough、David J. Whatrup、Joseph P. A. Harrity

  DOI：10.1021/ol701553j

  日期：2007.9.1

  A general and enantiospecific [3 + 3] reaction toward functionalized pyrans is reported that has been employed in the first enantioselective synthesis of (+)-rhopaloic acid B.