1,3-戊二醇,4,4-二甲基-1-苯基- | 107369-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,3-戊二醇,4,4-二甲基-1-苯基-
• 英文名称: 2,2-Dimethyl-5-phenyl-pentandiol-(3,5)
• 英文别名: 4,4-Dimethyl-1-phenylpentane-1,3-diol
• CAS: 107369-60-8；107369-62-0；132157-40-5；144712-80-1；144787-88-2；144787-89-3；18335-34-7
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: LDKYCWVDNYEZKC-UHFFFAOYSA-N

物化性质

• 熔点：
  105-106 °C
• 沸点：
  342.5±22.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-戊二醇,4,4-二甲基-1-苯基- 、 2,2-二甲氧基丙烷 在 camphor-10-sulfonic acid 作用下， 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
• 作为产物：
  描述：

  1-hydroxy-4,4-dimethyl-1-phenylpentan-3-one 在 甲醇 、 samarium diiodide 作用下， 以 乙二醇二甲醚 为溶剂， 以100%的产率得到1,3-戊二醇,4,4-二甲基-1-苯基-
  参考文献：
  名称：

  Solvent-Dependent Diastereoselectivities in Reductions of β-Hydroxyketones by SmI₂

  摘要：

  The reductions of a series of beta-hydroxyketones by Sml(2) were examined in THF, DME, and CH3CN using methanol as a proton source. Reductions in THF and DME typically lead to the syn diastereomer with DME providing higher diastereoselectivities. Reductions in CH3CN provided the anti diastereomer predominantly. This study reveals that solvation plays an important role in substrate reduction by Sml(2).

  DOI：

  10.1021/ol049129u

文献信息

• Regioselective, Borinic Acid-Catalyzed Monoacylation, Sulfonylation and Alkylation of Diols and Carbohydrates: Expansion of Substrate Scope and Mechanistic Studies
  作者：Doris Lee、Caitlin L. Williamson、Lina Chan、Mark S. Taylor

  DOI：10.1021/ja302549c

  日期：2012.5.16

  regioselective monofunctionalization of 1,2- and 1,3-diols are presented. Diarylborinic acid catalysis is shown to be an efficient and general method for monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups (7 examples, 88% average yield). In addition, the scope of the selective acylation, sulfonylation, and alkylation is extended to 1,2- and 1,3-diols not derived from carbohydrates

  介绍了二芳基硼酸催化的 1,2-和 1,3-二醇的区域选择性单官能化的合成和机械方面。二芳基硼酸催化被证明是对带有三个仲羟基的吡喃糖苷衍生物进行单甲苯基化的一种有效且通用的方法（7 个例子，平均产率 88%）。此外，选择性酰化、磺酰化和烷基化的范围扩展到非碳水化合物衍生的 1,2- 和 1,3- 二醇（28 个例子）；该方法的效率、通用性和操作简单性与包括广泛应用的有机锡催化或介导反应在内的最先进方案相比具有竞争力。使用竞争实验、动力学和催化剂结构-活性关系探索有机硼催化过程的机制细节。
• β-Functionalised organolithium compounds through a sulfur-lithium exchange
  作者：Francisco Foubelo、Ana Gutiérrez、Miguel Yus

  DOI：10.1016/s0040-4039(97)01008-3

  日期：1997.7

  The successive reaction of different β-hydroxy or β-amino thioethers 1a-d with n-butyl-lithium and an excess of lithium powder and a catalytic amount of DTBB in THF at −78°C leads to the formation of the corresponding β-functionalised organolithium compounds 2a-d, which by reaction with several electrophiles [D2O, ButCHO, PhCHO, Me2CO, (CH2)5CO] at temperatures ranging between −78 and 20°C yields,

  不同的β-羟基或β-氨基硫醚1a-d与正丁基锂，过量的锂粉和催化量的DTBB在-78°C的THF中连续反应导致形成相应的β-官能化有机锂化合物2A-d ，其通过与亲电子数[d反应2 O，卜吨CHO，苯甲醛中，Me 2 CO，（CH 2）5 CO]在温度范围-78至20℃之间的产率，用水解后水，预期的功能化醇或胺3aa-de（区域选择性）。
• Solvent-Dependent Diastereoselectivities in Reductions of β-Hydroxyketones by SmI₂
  作者：Pramod R. Chopade、Todd A. Davis、Edamana Prasad、Robert A. Flowers

  DOI：10.1021/ol049129u

  日期：2004.8.1

  The reductions of a series of beta-hydroxyketones by Sml(2) were examined in THF, DME, and CH3CN using methanol as a proton source. Reductions in THF and DME typically lead to the syn diastereomer with DME providing higher diastereoselectivities. Reductions in CH3CN provided the anti diastereomer predominantly. This study reveals that solvation plays an important role in substrate reduction by Sml(2).
• Zakharkin,L.I.; Savina,L.A., Journal of general chemistry of the USSR, 1967, vol. 37, p. 2441 - 2447
  作者：Zakharkin,L.I.、Savina,L.A.

  DOI：——

  日期：——
• 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.