2-(hydroxymethyl)-1-phenylbutan-1-one | 41531-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(hydroxymethyl)-1-phenylbutan-1-one
• 英文别名: 1-Phenyl-2-ethyl-1-propanon-3-ol
• CAS: 41531-82-2
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: JZHVNNHCEHMLMI-UHFFFAOYSA-N

物化性质

• 沸点：
  140-145 °C(Press: 5 Torr)
• 密度：
  1.058±0.06 g/cm3(Predicted)
• 保留指数：
  1540

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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-(hydroxymethyl)-1-phenylbutan-1-one 在 lithium hydride 、 四氯化钛 、 锂硼氢 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.67h， 生成
  参考文献：
  名称：

  The Role of theα-Stereogenic Center in the Control of Stereoselection in the Reduction ofα-Alkyl-β-hydroxy Ketones: A Highly Diastereoselective Protocol for the Synthesis of 1,2-syn-2-Alkyl-1,3-diols

  摘要：

  Accurate investigations on the role played by an alpha-stereogenic center in controlling the reduction of various classes of beta-hydroxy ketones allowed us to set up a general and highly diastereoselective protocol for the synthesis of 2-alkyl-1,3-diols with 1,2-syn relationship. This methodology is based on the conversion of a beta-hydroxy ketone into the corresponding titanium alcoholate that permits us to organize the substrate in a stable and rigid structure, which stereofacially favors attacking hydride ions. The use of THF as solvent makes available a variety of hydride donors that cover a large spectrum of steric demand: the choice of the more appropriate one depends on the conformational stability of the cyclic intermediate. Excellent results are obtained also in the presence of an additional stereogenic center in the beta-position, even if it exerts a concordant or an opposite steric effect with respect to the alpha-substituent.

  DOI：

  10.1002/1521-3765(20000717)6:14<2590::aid-chem2590>3.0.co;2-x
• 作为产物：
  描述：

  2-[1-Hydroxy-meth-(E)-ylidene]-1-phenyl-butan-1-one 在 (1,3-dimethylimidazol-2-ylidene)borane 、 2,4,5,6-四(9H-咔唑-9-基)异酞腈 、 水 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以88 %的产率得到2-(hydroxymethyl)-1-phenylbutan-1-one
  参考文献：
  名称：

  一种β-羟基酮类化合物及其合成方法

  摘要：

  本发明公开了一种β‑羟基酮类化合物及其合成方法。所述合成方法以烯醇酮为起始原料，在碱性环境中，经光催化剂催化、水作为添加剂，于光照、室温条件下，以N‑杂环卡宾硼烷作为供氢体通过氢化反应，生成β‑羟基酮类化合物。本发明的反应官能团兼容性强，收率高达90％，且产物具有官能团多样性。本发明的β‑羟基酮类化合物可作为有机合成前体，β‑羟基酮类化合物的骨架结构中3位羟基，可以进一步官能团化，得到药物分子骨架或者具有潜在生物活性的化合物等。

  公开号：

  CN116283524A

文献信息

• Visible-Light-Mediated Rose Bengal-Catalyzed α-Hydroxymethylation of Ketones with Methanol
  作者：Jingya Yang、Dongtai Xie、Hongyan Zhou、Shuwen Chen、Jiaokui Duan、Congde Huo、Zheng Li

  DOI：10.1002/adsc.201800467

  日期：2018.9.17

  A visible‐light‐mediated α‐hydroxymethylation of ketones using methanol as the hydroxymethylating reagent has been developed. Using 1 mol% rose bengal as the photosensitizer and air as the green oxidant, the reactions proceeded smoothly at room temperature. Experimental studies indicate the reaction proceeded via a radical pathway.

  已经开发出使用甲醇作为羟甲基化试剂的酮的可见光介导的α-羟甲基化方法。使用1mol％的孟加拉红作为光敏剂，并使用空气作为绿色氧化剂，该反应在室温下顺利进行。实验研究表明反应是通过自由基途径进行的。
• Catalytic Asymmetric Hydroxymethylation of Silicon Enolates Using an Aqueous Solution of Formaldehyde with a Chiral Scandium Complex
  作者：Shunpei Ishikawa、Tomoaki Hamada、Kei Manabe、Shū Kobayashi

  DOI：10.1021/ja047896i

  日期：2004.10.1

  Catalytic asymmetric hydroxymethylation of silicon enolates has been achieved. In this reaction, an aqueous solution of formaldehyde can be used to realize an easy and safe procedure, and high enantioselectivities have been obtained. This is the first example of catalytic asymmetric reactions in aqueous media with a chiral scandium complex.

  已经实现了硅烯醇化物的催化不对称羟甲基化。在该反应中，可以使用甲醛的水溶液来实现简单且安全的过程，并且获得了较高的对映选择性。这是在水性介质中与手性钪络合物进行催化不对称反应的第一个例子。
• Highly diastereoselective reduction of α-alkyl-β-hydroxy ketones with sodium and lithium boron hydrides via their titanium alcoholates
  作者：Giuseppe Bartoli、M.Cristina Bellucci、Marcella Bosco、Renato Dalpozzo、Enrico Marcantoni、Letizia Sambri

  DOI：10.1016/s0040-4039(99)00308-1

  日期：1999.4

  The reduction of α-alkyl-β-hydroxy ketones is highly syn-selective if carried out in THF on their Ti-alcoholate complexes with LiBH4 or L-Selectride® or N-selectride® depending on the bulkiness of the group bound to the carbonyl group.

  α-烷基-β羟基酮的还原是高顺式-选择性如果在THF中用的LiBH进行他们的Ti-醇化物配合物4或三仲丁基硼氢化锂®或N- selectride ®取决于组的键合于该蓬松性羰基。
• Bismuth Triflate−Chiral Bipyridine Complexes as Water-Compatible Chiral Lewis Acids
  作者：Shū Kobayashi、Tsuyoshi Ogino、Haruka Shimizu、Shunpei Ishikawa、Tomoaki Hamada、Kei Manabe

  DOI：10.1021/ol051965w

  日期：2005.10.1

  [reaction: see text] Catalytic asymmetric hydroxymethylation of silicon enolates with an aqueous formaldehyde solution has been developed using a chiral bismuth complex. This is the first example of highly enantioselective reactions using a chiral bismuth catalyst in aqueous media. In this paper, we have added Bi(OTf)(3)-1 complex as a "water-compatible Lewis acid". Bi(OTf)3 is unstable in the presence

  [反应：见正文]使用手性铋配合物已开发出用甲醛水溶液催化的烯醇硅的催化不对称羟甲基化反应。这是在水介质中使用手性铋催化剂进行高对映选择性反应的第一个例子。在本文中，我们添加了Bi（OTf）（3）-1配合物作为“与水相容的路易斯酸”。Bi（OTf）3在水的存在下不稳定，但被碱性配体稳定。
• Scandium(III) Fluoride as a Novel Catalyst for Hydroxymethylation of Dimethylsilyl Enolates in Aqueous Media
  作者：Shu Kobayashi、Masaya Kokubo

  DOI：10.1055/s-2008-1078409

  日期：2008.6

  Hydroxymethylation of dimethylsilyl (DMS) enolates using aqueous formaldehyde solution is catalyzed by scandium(III) fluoride (ScF3) in aqueous media to give the corresponding β-hydroxy ketones in good to excellent yields. Whilst the DMS enolate reactions are facile the TMS enolates react sluggishly under the same conditions. ScF3 has been shown to be a unique catalyst for this reaction.

  氟化钪（ScF3）在水介质中催化甲醛水溶液对二甲基硅烷基（DMS）烯醇酸盐的羟甲基化反应，可以得到相应的δ-羟基酮，收率良好甚至极佳。在相同条件下，DMS 烯醇反应容易，而 TMS 烯醇反应缓慢。研究表明，ScF3 是该反应的一种独特催化剂。