(Z)-(10S,11R)-11-Methoxymethoxy-10-methyl-heptadec-8-ene | 137920-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (Z)-(10S,11R)-11-Methoxymethoxy-10-methyl-heptadec-8-ene
• CAS: 137920-15-1
• 化学式: C₂₀H₄₀O₂
• 分子量: 312.536
• InChiKey: NKCBJDKLGIEPEG-TVUWTRKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  22.0
• 可旋转键数：
  16.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (Z)-(10S,11R)-11-Methoxymethoxy-10-methyl-heptadec-8-ene 在 sodium tetrahydroborate 、 二甲基硫 、 臭氧 作用下， 以 甲醇 为溶剂， 反应 0.34h， 生成 (2S,3R)-3-Methoxymethoxy-2-methyl-nonan-1-ol
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036
• 作为产物：
  描述：

  (10S,11R)-11-Methoxymethoxy-10-methyl-heptadec-8-yne 在 Lindlar's catalyst 氢气 作用下， 以 苯 为溶剂， 反应 1.0h， 生成 (Z)-(10S,11R)-11-Methoxymethoxy-10-methyl-heptadec-8-ene
  参考文献：
  名称：

  Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes

  摘要：

  Allenylstannanes (S)-4 and (R)-4, available in ca. 90% ee from alkynones 1 through reduction with the LiAlH4-Darvon alcohol or -ent-Darvon alcohol complex, followed by S(N)2' displacement on the derived mesylates (R)-3 or (S)-3 with Bu3SnLi.CuBr.Me2S, readily add to various aldehydes under Lewis acid catalysis to afford optically active homopropargylic alcohols with good to excellent syn diastereoselectivity. With 2-(benzyloxy)propanal (48), MgBr2-catalyzed reactions are highly stereoselective, affording the syn adduct 49 from the (S)-stannane (S)-4 and the anti adduct 52 from the (R)-stannane (R)-4. BF3-promoted additions give mainly or exclusively the syn adducts 49 and 51. Additions of (S)- and (R)-4 to (R)-3-(benzyloxy)-2-methylpropanal (61) yield the syn adducts 62 and 64 as major or exclusive products.

  DOI：

  10.1021/jo00030a036