1-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene | 1333398-09-6

• 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-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene
• 英文别名: 2-(Phenylmethoxymethyl)tetradec-2-enoxymethylbenzene；2-(phenylmethoxymethyl)tetradec-2-enoxymethylbenzene
• CAS: 1333398-09-6
• 化学式: C₂₉H₄₂O₂
• 分子量: 422.651
• InChiKey: DYVSAORSHSWYMF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  31
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.52
• 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-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene 在 Oxone 、 四丁基硫酸氢铵 、 edetate disodium 、 碳酸氢钠 、 methyl 4,6-O-benzylidene-2-O-methyl-α-D-arabino-hexopyranosid-3-ulose 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 生成 (-)-1-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene oxide 、 (-)-1-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene oxide
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014
• 作为产物：
  描述：

  在 sodium periodate 、 正丁基锂 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 3.0h， 生成 1-benzyloxy-2-(benzyloxymethyl)tetradec-2-ene
  参考文献：
  名称：

  New mannose-derived ketones as organocatalysts for enantioselective dioxirane-mediated epoxidation of arylalkenes. Part 3: Chiral ketones from sugars

  摘要：

  New D-arabino-hexopyranosid-3-uloses were synthesized by a simple method from mannopyranoside derivatives. The common skeleton possesses a tunable alkoxy group as steric sensor on carbon 2 of the sugar. The new ketones were employed in the dioxirane-mediated epoxidation of a range of trans- and trisubstituted arylalkenes giving enantiomeric excesses from low to good (30-90%). The effect of the size of the steric sensor on the enantioselectivity was also studied. The least bulky group (methoxy group) enhanced the stereoselectivity (up to 90% ee toward triphenylethylene). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.07.014