4-tert-butyl-2,2-dimethyl-6-phenyl-[1,3]dioxane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-tert-butyl-2,2-dimethyl-6-phenyl-[1,3]dioxane
• 英文别名: (4R,6S)-4-tert-butyl-2,2-dimethyl-6-phenyl-1,3-dioxane
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: IUOVSLQAVCLTOD-UONOGXRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-hydroxy-4,4-dimethyl-1-phenylpentan-3-one 在 samarium diiodide 、 camphor-10-sulfonic acid 、 水 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 4-tert-butyl-2,2-dimethyl-6-phenyl-[1,3]dioxane
  参考文献：
  名称：

  Reduction of β-Hydroxyketones by SmI₂/H₂O/Et₃N

  摘要：

  Reduction of a series of beta-hydroxyketones by SmI2/H2O/Et3N provided 1,3-diols in quantitative yields. The reactions were exceedingly clean with no byproduct formation, negating the need for further purification. Most reactions provided moderate to excellent diastereoselectivity with syn-diols as the major isomer in most instances.

  DOI：

  10.1021/ol047835p

文献信息

• Experimental Evidence for Chair-Like Transition States in Aldol Reactions of Methyl Ketone Lithium Enolates:  Stereoselective Synthesis and Utilization of a Deuterium-Labeled Enolate as a Probe of Reaction Stereochemistry
  作者：Christopher M. Liu、William J. Smith、Darin J. Gustin、William R. Roush

  DOI：10.1021/ja050730c

  日期：2005.4.1

  Aldol reactions of methyl ketone lithium enolates proceed via chairlike Zimmerman-Traxler transition states with 7:1 to 50:1 preference over alternative, boatlike transition structures, as determined by studies involving the configurationally stable deuterium-labeled enol silane 18 as the lithium enolate precursor.

  甲基酮烯醇锂的羟醛反应通过椅子状 Zimmerman-Traxler 过渡态进行，7:1 至 50:1 优先于替代的船状过渡结构，这是由涉及构型稳定的氘标记烯醇硅烷 18 作为烯醇锂前体的研究确定的.
• Chiral organosilicon compounds in asymmetric synthesis of chiral 1,3-diols
  作者：T. H. Chan、K. T. Nwe

  DOI：10.1021/jo00049a012

  日期：1992.11

  Chiral 1,3-diols can be prepared in high enantiomeric purity (>99% ee) from the reactions of the chiral silylcarbanion 2 with epoxides followed by oxidative cleavage of the carbon-silicon bond with hydrogen peroxide. The absolute configurations of some of the chiral 1,3-diols were determined by circular dichroism (CD).
• Reduction of β-Hydroxyketones by SmI₂/H₂O/Et₃N
  作者：Todd A. Davis、Pramod R. Chopade、Göran Hilmersson、Robert A. Flowers

  DOI：10.1021/ol047835p

  日期：2005.1.1

  Reduction of a series of beta-hydroxyketones by SmI2/H2O/Et3N provided 1,3-diols in quantitative yields. The reactions were exceedingly clean with no byproduct formation, negating the need for further purification. Most reactions provided moderate to excellent diastereoselectivity with syn-diols as the major isomer in most instances.