(+/-)-3-acetoxy-1-phenylbutan-1-one | 76926-84-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-3-acetoxy-1-phenylbutan-1-one
• 英文别名: 3-acetoxybutyrophenone；(4-oxo-4-phenylbutan-2-yl) acetate
• CAS: 76926-84-6
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: MPODLFKNAJBQES-UHFFFAOYSA-N

物化性质

• 沸点：
  314.7±25.0 °C(Predicted)
• 密度：
  1.080±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-3-acetoxy-1-phenylbutan-1-one 在 水 、 scandium tris(trifluoromethanesulfonate) 作用下， 以 甲醇 为溶剂， 反应 112.0h， 以39%的产率得到3-羟基-1-苯基-1-丁酮
  参考文献：
  名称：

  Scandium Trifluoromethanesulfonate-Catalyzed Cleavage of Esters Bearing a Coordinative Group at a Vicinal Position

  摘要：

  研究发现，三氟甲磺酸钪是一种路易斯酸催化剂，可选择性地裂解含有邻近酯分子的配位基团的酯。反应在室温下的弱酸性条件下进行；催化剂可以回收和重复使用。即使是 α-乙酰氧基酮也能脱乙酰化而不发生外消旋化。在紫杉醇的 C-10 处实现了选择性单去乙酰化。

  DOI：

  10.1246/bcsj.72.1553
• 作为产物：
  描述：

  3-羟基-1-苯基-1-丁酮 在 4-二甲氨基吡啶 、 乙酸酐 、 三乙胺 作用下， 以63%的产率得到(+/-)-3-acetoxy-1-phenylbutan-1-one
  参考文献：
  名称：

  Cobalt(II) chloride catalyzed acylation of alcohols with acetic anhydride: scope and mechanism

  摘要：

  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.

  DOI：

  10.1021/jo00033a020

文献信息

• One-Pot Preparation of Alcohols from Aromatic Olefins and Acrylic Acid Derivatives by Cobalt(II) Porphyrin-Catalyzed Reductive Oxygenation Followed by Reduction with Trimethyl Phosphite
  作者：Yoh-ichi Matsusita、Kazuhiro Sugamoto、Takanao Matsui

  DOI：10.1246/cl.1993.925

  日期：1993.6

  acid derivatives were converted to benzyl alcohols and α-hydroxyalkanoic acid derivatives in good yields by the reductive oxygenation with oxygen and triethylsilane in the presence of a catalytic amount of cobalt(II) porphyrin followed by treating the reaction mixture with trimethyl phosphite.

  在催化量的钴 (II) 卟啉存在下，通过氧和三乙基硅烷的还原氧化，各种芳族烯烃和丙烯酸衍生物以良好的收率转化为苯甲醇和 α-羟基链烷酸衍生物，然后用三甲基卟啉处理反应混合物。亚磷酸盐。
• Expanding the Substrate Specificity of <i>Thermoanaerobacter pseudoethanolicus</i> Secondary Alcohol Dehydrogenase by a Dual Site Mutation
  作者：Musa M. Musa、Odey Bsharat、Ibrahim Karume、Claire Vieille、Masateru Takahashi、Samir M. Hamdan

  DOI：10.1002/ejoc.201701351

  日期：2018.2.14

  The authors acknowledge the support provided by the Deanship of Scientific Research (DSR) at King Fahd University of Petroleum and Minerals (KFUPM) for funding this work under project number IN151032. They also acknowledge the supported by baseline research fund to S.M.H. by King Abdullah University of Science and Technology.

  作者感谢法赫德国王石油和矿产大学 (KFUPM) 科学研究院长 (DSR) 为在项目编号 IN151032 下资助这项工作提供的支持。他们还感谢阿卜杜拉国王科技大学对 SMH 的基线研究基金的支持。
• Scandium trifluoromethanesulfonate-catalyzed mild, efficient, and selective cleavage of acetates bearing a coordinative group
  作者：Hiroshi Kajiro、Shuichi Mitamura、Atsunori Mori、Tamejiro Hiyama

  DOI：10.1016/s0040-4039(99)00003-9

  日期：1999.2

  Scandium trifluoromethanesulfonate is a useful Lewis acid catalyst for cleavage of acetates containing coordinative groups adjacent to the acetyl carbonyl. The reaction proceeds under weak acidic conditions at room temperature. Racemizable alpha-keto acyloxy compounds are deacetylated without racemization. Selective mono-deacetylation at the 10-position of paclitaxel has been achieved. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Hosokawa, Takahiro; Shinohara, Toru; Ooka, Yoshiharu, Chemistry Letters, 1989, p. 2001 - 2004
  作者：Hosokawa, Takahiro、Shinohara, Toru、Ooka, Yoshiharu、Murahashi, Shun-Ichi

  DOI：——

  日期：——
• HOSOKAWA, TAKAHIRO;SHINOHARA, TORU;OOKA, YOSHIHARU;MURAHASHI, SHUN-ICHI, CHEM. LETT.,(1989) N1, C. 2001-2004
  作者：HOSOKAWA, TAKAHIRO、SHINOHARA, TORU、OOKA, YOSHIHARU、MURAHASHI, SHUN-ICHI

  DOI：——

  日期：——