(3S,4R)-2,4-dimethyl-5-tridecyn-3-ol | 157379-06-1

• 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: (3S,4R)-2,4-dimethyl-5-tridecyn-3-ol
• 英文别名: (3S,4R)-2,4-dimethyltridec-5-yn-3-ol
• CAS: 157379-06-1
• 化学式: C₁₅H₂₈O
• 分子量: 224.387
• InChiKey: ZJEJLNHBWIRXIR-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  undec-3-yn-2-one 在 magnesium bromide lithium aluminium tetrahydride 、 copper(I) bromide dimethylsulfide complex 、 三丁基锡锂 、 (R)-Chirald 、 三乙胺 、 二异丙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 30.0h， 生成 (3S,4R)-2,4-dimethyl-5-tridecyn-3-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

文献信息

• Diastereoselective additions of allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00313a007

  日期：1990.12

  The allenylstannane 4 undergoes highly syn selective additions to alpha-branched aldehydes 8b and 8c in the presence of BF3.OEt2. With the beta-alkoxy aldehyde 21, Cram-Felkin addition results with BF3.Oet2 as the Lewis acid, whereas MgBr2 leads to chelation-controlled addition.
• Synthesis of Syn and Anti Homopropargylic and Allenic Alcohols through Diastereoselective SE2' Addition of a Common Chiral Allenylstannane Precursor to Aldehydes
  作者：James A. Marshall、Jolyon Perkins

  DOI：10.1021/jo00092a001

  日期：1994.7

  The (tri-n-butylallenyl)stannanes 3 and 17 afford the allenyl adducts 8 and 19 upon brief treatment with stannic chloride and then addition of isobutyraldehyde, whereas preequilibration with SnCl4 and subsequent aldehyde addition leads to the anti homopropargylic adducts 5 and 19.
• Synthesis of enantioenriched homopropargylic alcohols through diastereoselective SE' additions of chiral allenylstannanes to aldehydes
  作者：James A. Marshall、Xiao Jun Wang

  DOI：10.1021/jo00030a036

  日期：1992.2

  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.