(R)-cyclohexyl-methoxymethoxy-acetaldehyde | 172288-95-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-cyclohexyl-methoxymethoxy-acetaldehyde
• 英文别名: (2R)-2-cyclohexyl-2-(methoxymethoxy)acetaldehyde
• CAS: 172288-95-8
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: KEFHUIMQXZXMLZ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cyclopropylphenylethyne 、 (R)-cyclohexyl-methoxymethoxy-acetaldehyde 在 bis(1,5-cyclooctadiene)nickel (0) 地昔帕明 、 三乙基硼 、 (S)-(+)-2-异丙基-5-甲基二苯磷 作用下， 以 乙酸乙酯 为溶剂， 反应 20.0h， 以62%的产率得到(E)-(1R,2S)-1-cyclohexyl-3-cyclopropyl-1-methoxymethoxy-4-phenyl-but-3-en-2-ol
  参考文献：
  名称：

  anti-1,2-Diols via Ni-Catalyzed Reductive Coupling of Alkynes and α-Oxyaldehydes

  摘要：

  Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiornerically enriched alpha-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes.

  DOI：

  10.1021/ol050881k
• 作为产物：
  描述：

  (R)-1-cyclohexylethane-1,2-diol 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 (R)-cyclohexyl-methoxymethoxy-acetaldehyde
  参考文献：
  名称：

  anti-1,2-Diols via Ni-Catalyzed Reductive Coupling of Alkynes and α-Oxyaldehydes

  摘要：

  Ni-catalyzed reductive coupling of aryl alkynes (1) and enantiornerically enriched alpha-oxyaldehydes (2) afford differentiated anti-1,2-diols (3) with high diastereoselectivity and regioselectivity, despite the fact that the methoxymethyl (MOM) and para-methoxybenzyl (PMB) protective groups typically favor syn-1,2-diol formation in carbonyl addition reactions of this family of aldehydes.

  DOI：

  10.1021/ol050881k

文献信息

• Chelation control associated with organometallic addition reactions in water. The high stereoselectivity offered by α- and β-hydroxyl substituents obviates the need for protecting groups
  作者：L Paquette

  DOI：10.1016/00404-0399(50)1439o-

  日期：1995.9.18

  High stereoselectivities have been observed for indium-promoted allylations of alpha- and beta-hydroxy aldehydes in aqueous media, with strong implication that chelate control can continue to operate in water.