2-苄基-1-羟基-3-丁酮 | 127841-27-4

• 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: 2-苄基-1-羟基-3-丁酮
• 英文名称: 4-phenyl-3-hydroxymethyl-2-butanone
• 英文别名: 2-benzyl-1-hydroxy-3-butanone；3-benzyl-4-hydroxy-2-butanone；3-Benzyl-4-hydroxybutan-2-one
• CAS: 127841-27-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: QIEPEXBZWZNCAY-UHFFFAOYSA-N

物化性质

• 沸点：
  312.3±22.0 °C(Predicted)
• 密度：
  1.068±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-苄基-1-羟基-3-丁酮 在 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 0.5h， 生成 3-benzyl-2-pentanone
  参考文献：
  名称：

  Functional group hybrids. Reactivity of .alpha.'-nucleofuge .alpha.,.beta.-unsaturated ketones. 1. Reactions with organocopper reagents

  摘要：

  A series of alpha-nucleofuge alpha',beta'-unsaturated ketones encompassing a variety of structural types and nucleofuges was prepared. Treatment of these compounds with lithium dimethylcuprate or methylcopper leads primarily to either reductive cleavage of the alpha-nucleofuge or conjugate addition. Good alpha-nucleofuges favored the reduction pathway while poorer nucleofuges favored conjugate addition.

  DOI：

  10.1021/jo00024a014
• 作为产物：
  描述：

  2-苄基乙酰乙酸乙酯 生成 2-苄基-1-羟基-3-丁酮
  参考文献：
  名称：

  由β-酮酸酯合成α，β-不饱和δ-内酯的快速有效的成环方案

  摘要：

  β-酮酸酯6a–3转化为β-酮醇7a–3，它们与膦酸酯9a–e同源。分子内霍纳-沃兹沃思-埃蒙斯反应可提供出色的总收率的δ内酯10a-d。

  DOI：

  10.1016/s0040-4039(00)74216-x

文献信息

• Expeditious and efficient annulation protocol for the synthesis of α,β-unsaturated δ-lactones from β-keto esters
  作者：A. Nangia、P. Bheema Rao

  DOI：10.1016/s0040-4039(00)74216-x

  日期：1992.4

  β-Keto esters 6a–3 are transformed into β-keto alcohols 7a–3, which are homologated to phosphonates 9a–e. Intramolecular Horner-Wadsworth-Emmons reaction affords δlactones 10a–d in excellent overall yields.

  β-酮酸酯6a–3转化为β-酮醇7a–3，它们与膦酸酯9a–e同源。分子内霍纳-沃兹沃思-埃蒙斯反应可提供出色的总收率的δ内酯10a-d。
• Efficient Synthesis of α-(Hydroxymethyl) Ketones Not Available Through Aldol-Type Processes
  作者：Shawn R. Hitchcock、Françoise Perron、Van A. Martin、Kim F. Albizati

  DOI：10.1055/s-1990-27093

  日期：——

  An efficient synthesis of α-(hydroxymethyl) ketones from β-keto esters has been developed, which is experimentally simple, amenable to large scale production and provides products of high purity without resort to chromatography in most cases. The method is a useful alternative and complement to condensation processes.

  已开发出一种从β-酮酯高效合成α-(羟甲基)酮的方法，该方法实验简单，适合大规模生产，并且在大多数情况下无需借助色谱法即可提供高纯度产品。此方法是对缩合过程的有用替代和补充。
• Alkylative carbonyl transposition of dihydro-α-pyrones to dihydro-α-pyrones
  作者：A. Nangia、P.Bheema Rao

  DOI：10.1016/s0040-4039(00)77655-6

  日期：1993.4

  Dihydro-α-pyrones (2) are prepared from β-hydroxy ketones (1). Dihydropyrones (2) are transformed to unsaturated δ-lactones (4) via an alkylative 1,3-carbonyl transposition.

  二氢α吡喃酮（2）由β羟基酮（制备1）。二氢吡喃酮（2）通过烷基化的1，3-羰基转座转化为不饱和δ-内酯（4）。
• Chemistry of dioxenium cations. Synthetic and mechanistic studies on the stereocontrolled formation of tetrahydropyrans from homoallylic alcohols and ortho esters
  作者：Francoise Perron-Sierra、Michele A. Promo、Van A. Martin、Kim F. Albizati

  DOI：10.1021/jo00021a043

  日期：1991.10

  Despite their long history, dioxenium cations are underutilized reactive synthetic intermediates. It was found that ortho esters and homoallylic alcohols in the presence of Lewis acids provide 4-heterosubstituted pyranosides in a stereoselective manner. The mechanistic course of events was supported by control experiments and synthesis of a putative mixed ortho ester intermediate which exhibited identical reactivity. A transition state for termination of the dioxenium cation-olefin cyclization is proposed, involving intramolecular delivery of chloride by a coordinated tin species. Structure-reactivity relationships indicate that a cation-stabilizing substituent (alkyl or alkoxy) at the internal position of the olefin is required for cyclization. A variety of 3-alkyl-substituted homoallylic alcohols cyclize cleanly to substituted 2-alkoxytetrahydropyrans in good yield. beta-silyloxy silyl enol ethers were found to smoothly provide 4-oxotetrahydropyranosides when subjected to the same reaction conditions. For these substrates, the course of the cyclization proceeds in a different manner involving a rapid intermolecular Mukaiyama aldol condensation followed by transacetalization.
• Van Martin; Murray, Desmond H.; Pratt, Norman E., Journal of the American Chemical Society, 1990, vol. 112, # 19, p. 6965 - 6978
  作者：Van Martin、Murray, Desmond H.、Pratt, Norman E.、Zhao, Yun-Bo、Albizati, Kim F.

  DOI：——

  日期：——