| 142508-84-7

• 分子结构分类: 有机化合物 - 有机杂环化合物
• CAS: 142508-84-7；142562-72-9
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: PKJNJKDAADTQSF-GIJJTGMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  在 Pd-BaSO₄ 喹啉 、 四氧化锇 、 N-甲基吲哚酮 、 三氟化硼乙醚 、 氢气 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 生成
  参考文献：
  名称：

  Coupling of alkynyl organometallics with 4-acetoxy-1,3-dioxanes: Synthesis of propargylic and allylic anti-1,3-diols

  摘要：

  Alkynyl diethylalanes and stannanes couple with 4-acetoxy-1,3-dioxane 1 in the presence of BF3 . OEt2 to give acetal protected propargylic anti-1,3-diols 2 in high yield, with exquisite diastereoselectivity and little acetal epimerization. These propargylic dioxanes 2 are useful intermediates for further diastereoselective reactions. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00512-7
• 作为产物：
  描述：

  (2S,6S)-6-Hexyl-2-(2-hydroxy-octyl)-[1,3]dioxan-4-ol 在 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  A practical preparation of .alpha.-alkoxylithium reagents: synthesis of syn or anti 1,3-diols

  摘要：

  Phenylthio acetals 3 are easily prepared from beta-hydroxy aldehydes and can be reduced to anti alkyllithiums 7 and subsequently equilibrated to syn alkyllithiums 9 with excellent stereoselectivity and in good overall yield. A practical preparation of 3 and a reductive lithiation procedure using catalytic naphthalene makes these alkyllithium reagents conveniently available on a multigram scale.

  DOI：

  10.1021/jo00042a005

文献信息

• <i>Anti</i>-1,3-diols by Addition of Dialkylzinc Reagents to 4-Acetoxy-1,3-dioxanes
  作者：Noel A. Powell、Scott D. Rychnovsky

  DOI：10.1021/jo982264y

  日期：1999.3.1

  Dialkylzincs couple with 4-acetoxy-6-alkyl-1,3-dioxanes in the presence of trimethylsilyl triflate (TMSOTf) to form trans-4,6-dialkyl-1,3-dioxanes with excellent diastereoselectivities. These dioxanes could be deprotected to yield anti-1,3-diols. A variety of functional groups are tolerated in the dialkylzinc, although silyl and benzyl ethers led to diminished diastereoselectivities. Substituents at the C5-position of the dioxane ring have little effect on the selectivity, while small C2 (acetal) substituents led to slightly reduced diastereoselectivity. These couplings work best with cyclic acetals, which can be difficult to hydrolyze. The 4-(benzyloxy)butanal (BOB) acetal has been developed as a new cyclic acetal protecting group that is compatible with dialkylzinc coupling reactions. BOB protecting groups are easily removed by catalytic hydrogenation followed by mild acid hydrolysis.