methyl (E,5S,6S)-6-hydroxy-4,5-dimethyl-7-phenylmethoxyhept-3-enoate | 146980-53-2

• 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: methyl (E,5S,6S)-6-hydroxy-4,5-dimethyl-7-phenylmethoxyhept-3-enoate
• CAS: 146980-53-2
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: FWZZEDMALWLQEC-POPWGMBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (E,5S,6S)-6-hydroxy-4,5-dimethyl-7-phenylmethoxyhept-3-enoate 在 sodium periodate 、 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 生成 5-(benzyloxy)-4-hydroxy-3-methylpentan-2-one
  参考文献：
  名称：

  Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes

  摘要：

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.

  DOI：

  10.1021/jo00057a007
• 作为产物：
  描述：

  (E)-2-methyl-2-buten-1-ol 在 4-二甲氨基吡啶 、 四氯化锡 、 丙酸 lithium aluminium tetrahydride 、 正丁基锂 、 三氟化硼乙醚 、 叔丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 、 正戊烷 为溶剂， 反应 19.0h， 生成 methyl (E,5S,6S)-6-hydroxy-4,5-dimethyl-7-phenylmethoxyhept-3-enoate
  参考文献：
  名称：

  Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes

  摘要：

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.

  DOI：

  10.1021/jo00057a007

文献信息

• Acyclic diastereoselectivity in the Lewis acid promoted additions of chiral, .beta.-methyl-substituted (E)-crotylsilanes with achiral aldehydes
  作者：James S. Panek、Pier F. Cirillo

  DOI：10.1021/jo00057a007

  日期：1993.2

  The diastereoselection in the Lewis acid promoted addition of chiral, beta-methyl-substituted (E)-crotylsilanes (S)-1a and (R)-1b with alpha-(benzyloxy)acetaldehyde (2) is reversed from syn to anti by changing the Lewis acid from BF3.OEt2 (non-chelation-controlled conditions) to MgBr2.OEt2, a Lewis acid that is capable of forming a strong chelate with the alpha-(benzyloxy) group of the aldehyde. The reactions result in the formation of the syn homoallylic alcohols 3 or the complementary anti products 4.