1,4-diacetoxy-1-phenylbutane | 139313-42-1

• 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: 1,4-diacetoxy-1-phenylbutane
• 英文别名: 1,4-diacetoxy-1-phenyl-butane；1,4-Diacetoxy-1-phenyl-butan；(4-Acetyloxy-4-phenylbutyl) acetate
• CAS: 139313-42-1
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: BZNLNYDPOQLQAK-UHFFFAOYSA-N

物化性质

• 沸点：
  344.1±35.0 °C(Predicted)
• 密度：
  1.092±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-diacetoxy-1-phenylbutane 、 烯丙基三甲基硅烷 在 indium(III) bromide 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 以48%的产率得到4-phenylacetoxyhept-6-ene
  参考文献：
  名称：

  Kim, Sang Hee; Shin, Chul; Pae, Ae Nim, Synthesis, 2004, # 10, p. 1581 - 1584

  摘要：

  DOI：
• 作为产物：
  描述：

  苯丁酮 在 sodium amalgam 、 乙醇 、 氯仿 、 二氯氧化铬 作用下， 生成 1,4-diacetoxy-1-phenylbutane
  参考文献：
  名称：

  Burcker, Annales de Chimie (Cachan, France), 1882, vol. <5> 26, p. 476

  摘要：

  DOI：

文献信息

• Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism
  作者：Javed Iqbal、Rajiv Ranjan Srivastava

  DOI：10.1021/jo00033a020

  日期：1992.3

  Cobalt(II) chloride catalyzes the acetylation of a variety of alcohols with acetic anhydride in excellent yield. Primary hydroxyl groups can be selectively acylated in the presence of secondary and tertiary ones while the secondary hydroxyl groups can be preferentially acetylated in the presence of tertiary ones. Tertiary alcohols have been found to give ketones, acetoacetates, olefins, and diketene in addition to the acetate. The beta-hydroxy esters and ketones can be acylated under these conditions without any elimination, and this reaction has been compared with 4-(dimethylamino)pyridine (DMAP)-mediated acylations where elimination of the resulting beta-acetoxy carbonyl compound is observed. A detailed investigation of the acylation of tertiary alcohols has revealed that these reactions proceed via a tertiary alkoxy radical and ketene. A mechanism for these acylations is proposed by invoking an electron-transfer process.
• B(C₆F₅)₃-Catalyzed Allylation of Secondary Benzyl Acetates with Allylsilanes
  作者：Michael Rubin、Vladimir Gevorgyan

  DOI：10.1021/ol016300i

  日期：2001.8.1

  [GRAPHICS]A highly effective protocol for allylation of secondary benzylic alcohol derivatives with allylsilanes in the presence of catalytic amounts of B(C6F5)(3) has been developed. Some additional functionalities, such as bromo, acetoxy, and primary benzyloxy groups, were tolerated under these conditions.