(2R,3S,4S)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane | 137943-34-1

• 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: (2R,3S,4S)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane
• 英文别名: (4S,5R)-2,2,5-trimethyl-4-[(1S)-1-phenylmethoxyethyl]-1,3-dioxane
• CAS: 137943-34-1
• 化学式: C₁₆H₂₄O₃
• 分子量: 264.365
• InChiKey: SDIKDVLHPZHVKU-IPYPFGDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (S)-2-苄氧基丙醛 在 Lindlar's catalyst 、 magnesium bromide sodium tetrahydroborate 、 二甲基硫 、 氢气 、 对甲苯磺酸 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 1.84h， 生成 (2R,3S,4S)-2-methyl-4-(benzyloxy)-1,3-(isopropylidenedioxy)pentane
  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

• Surprising Role of Aryl Halides in Nickel-Catalyzed Reductive Aldol Reactions
  作者：Christa C. Chrovian、John Montgomery

  DOI：10.1021/ol063028+

  日期：2007.2.1

  [reaction: see text] A new nickel-catalyzed method for the reductive aldol addition of acrylates and aldehydes has been developed. An unexpected requirement for an aryl iodide additive was found in the process, and the effect was shown to be linked to an initiation step.

  [反应：见正文]已经开发了一种新的镍催化的丙烯酸酯和醛的醛醇缩合加成方法。在该方法中发现了对芳基碘化物添加剂的出乎意料的要求，并且显示出该效果与引发步骤有关。
• 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.