1-{[(S)-1-(Bbenzyloxy)hex-5-yn-3-yloxy]methyl}benzene | 528598-36-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-{[(S)-1-(Bbenzyloxy)hex-5-yn-3-yloxy]methyl}benzene
• 英文别名: [(3S)-3-phenylmethoxyhex-5-ynoxy]methylbenzene
• CAS: 528598-36-9
• 化学式: C₂₀H₂₂O₂
• 分子量: 294.393
• InChiKey: SNUROLKRKUVVSU-FQEVSTJZSA-N

物化性质

• 沸点：
  414.3±45.0 °C(predicted)
• 密度：
  1.055±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-{[(S)-1-(Bbenzyloxy)hex-5-yn-3-yloxy]methyl}benzene 在 正丁基锂 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 生成 [(4R,5R)-5-[(5S)-5,7-bis(phenylmethoxy)hept-2-ynyl]-2,2-dimethyl-1,3-dioxolan-4-yl]methanol
  参考文献：
  名称：

  Total Synthesis of a Cytotoxic Acetogenin, Pyranicin

  摘要：

  The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI2-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn,-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degreesC followed by reduction and deprotection afforded 1 in good overall yield.

  DOI：

  10.1021/ol034323m
• 作为产物：
  描述：

  (S)-1-Benzyloxy-6-trimethylsilanyl-hex-5-yn-3-ol 在 甲醇 、 四丁基碘化铵 、 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-{[(S)-1-(Bbenzyloxy)hex-5-yn-3-yloxy]methyl}benzene
  参考文献：
  名称：

  Total Synthesis of a Cytotoxic Acetogenin, Pyranicin

  摘要：

  The first total synthesis of a new cytotoxic acetogenin, pyranicin (1), is described. SmI2-induced reductive cyclization of beta-alkoxy acrylate 4 proceeded stereoselectively to give 16,20-syn,-19,20-trans-THP derivative 14, which was efficiently transformed into the 19,20-cis-THP derivative 18 through Mitsunobu lactonization. Wittig reaction of the phosphonium salt 2 obtained therefrom with butenolide 3 at -78 degreesC followed by reduction and deprotection afforded 1 in good overall yield.

  DOI：

  10.1021/ol034323m

文献信息

• An Efficient Convergent Access to Spiroketal Segment of (+)-Spiroxaline Methyl Ether
  作者：Narshinha Argade、Mandeep Singh

  DOI：10.1055/s-0030-1258456

  日期：2011.4

  Starting from trimethylsilylacetylene, a facile synthesis of optically pure spiroketal unit of (+)-spiroxaline methyl ether has been described. The synthesis entails stepwise alkylation and acylation of an alkyne with two different readily available chiral building blocks followed by the reductive in situ regio- and stereoselective spiroketalization pathway. alkyne - (R)-oxirane - (R)-γ-valerolactone

  从三甲基甲硅烷基乙炔开始，已经描述了容易合成光学纯的（+）-螺氧杂环林甲基醚的螺酮基单元。合成需要使用两个易于获得的手性结构单元逐步进行炔烃的烷基化和酰化，然后进行还原性原位区域和立体选择性螺酮缩合途径。 炔烃-（R）-环氧乙烷-（R）-γ-戊内酯-亲核反应-（+）-螺段合成