2-hydroxy-2,2-diphenyl-1-(p-tolyl)ethanone | 4625-47-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2-hydroxy-2,2-diphenyl-1-(p-tolyl)ethanone
• 英文别名: 2-Hydroxy-1-(4-methylphenyl)-2,2-diphenylethanone
• CAS: 4625-47-2
• 化学式: C₂₁H₁₈O₂
• 分子量: 302.373
• InChiKey: NTXZTVSEWGKEBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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-hydroxy-2,2-diphenyl-1-(p-tolyl)ethanone 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以69%的产率得到9H-fluoren-9-yl-(4-methylphenyl)methanone
  参考文献：
  名称：

  Regioselective Superacid-Catalyzed Electrocyclization of Diphenylmethyl Cations to Fluorenes, Phenanthrols and Benzofurans

  摘要：

  在超级酸的存在下，α-苄酰二苯基甲醇的阳离子电环化反应可以获得良至中等产率的芴、菲醇和苯并呋喃。一次取代导致区域选择性的阳离子电环化反应。

  DOI：

  10.1055/s-2001-16083
• 作为产物：
  描述：

  2,2-二苯基乙酸 在 aluminum (III) chloride 、 溴 、 溶剂黄146 、 sodium hydroxide 、 三氯化磷 作用下， 生成 2-hydroxy-2,2-diphenyl-1-(p-tolyl)ethanone
  参考文献：
  名称：

  制备2-羟基-2,2-二苯基-1-(对甲苯基)乙酮 的方法

  摘要：

  本发明涉及备2‑羟基‑2,2‑二苯基‑1‑(对甲苯基)乙酮的方法，包括：a).2,2‑二苯基乙酸与三氯化磷反应制备2,2‑二苯基乙酰氯，b).2,2‑二苯基乙酰氯与甲苯反应制备2,2‑二苯基‑1‑(对甲苯基)乙酮，c).2,2‑二苯基‑1‑对甲苯基乙酮与溴素反应制备2‑溴‑2,2‑二苯基‑1‑(对甲苯基)乙酮，d).2‑溴‑2,2‑二苯基‑1‑(对甲苯基)乙酮与碱液反应制备2‑羟基‑2,2‑二苯基‑1‑(对甲苯基)乙酮。本发明合成工艺简单，大大降低了反应的危险性，减少了对于环境的污染，有利于放大和工业化生产。

  公开号：

  CN105669406B

文献信息

• Intramolecular and intermolecular ketone–ester reductive coupling reactions promoted by samarium(II) iodide
  作者：Yunkui Liu、Yongmin Zhang

  DOI：10.1016/s0040-4039(01)01107-8

  日期：2001.8

  Intramolecular and intermolecular ketone–ester reductive coupling reactions promoted by SmI2 have been studied. Substituted 2-hydroxy-5-ethoxycarbonylcyclopentanones, 5-ethoxycarbonylcyclopentenones and α-ketols were prepared in moderate to good yields at room temperature or under reflux under neutral conditions.

  已经研究了由SmI 2促进的分子内和分子间酮-酯还原偶联反应。在室温下或在中性条件下在回流下以中等至良好的产率制备2-羟基-5-乙氧基羰基环戊烯酮，5-乙氧基羰基环戊烯酮和α-酮醇。
• A novel lanthanum metal-assisted reaction of diaryl ketones and electrophiles
  作者：Rui Umeda、Masashi Ninomiya、Toshiaki Nishino、Makoto Kishida、Shunsuke Toiya、Tomoki Saito、Yutaka Nishiyama、Noboru Sonoda

  DOI：10.1016/j.tet.2014.12.089

  日期：2015.2

  corresponding unsymmetrical 1,2-diols in moderate to good yields. α-Hydroxy ketones were prepared by the lanthanum metal-assisted reaction of diaryl ketones with esters or nitriles, followed by hydrolysis with aq HCl. It is interesting to note that for the epoxides, the coupling reaction proceeded via the Meinwald rearrangement of epoxides to give the corresponding 1,2-diols.

  已经开发出新颖且有效的镧形成的金属芳基辅助的二芳基酮和各种亲电试剂，例如羰基化合物，酯，腈和环氧化物的碳-碳键形成。当在镧金属和催化量的碘存在下使二芳基酮与二烷基酮反应时，交叉频哪醇偶联反应进行，以中等至良好的产率得到相应的不对称1,2-二醇。通过二芳基酮与酯或腈的镧金属辅助反应，然后用HCl水溶液水解，制备α-羟基酮。有趣的是，对于环氧化物，偶联反应通过环氧化物的迈因瓦尔德重排进行，得到相应的1,2-二醇。
• Samarium(II) Iodide-Promoted Intermolecular and Intramolecular Ketone-Nitrile Reductive Coupling Reactions
  作者：Longhu Zhou、Yongmin Zhang、Daqing Shi

  DOI：10.1055/s-2000-6220

  日期：——

  Samarium(II) iodide, a strong one-electron transfer reducing reagent, has been successfully utilized for the intermolecular and intramolecular reductive coupling reactions of ketones with nitriles. α-Hydroxy ketones, monocyclic, fused bicyclic α-hydroxy ketones and monocyclic α-amino alcohols composed of a number of substitution patterns have been prepared in good yields at room temperature or reflux under neutral conditions. The procedure can avoid overreduction of the resulting of α-hydroxy ketones or α-amino alcohols. The crystal structures of monocyclic α-amino alcohols are reported.

  钐（II）碘化物是一种强的一电子转移还原试剂，已成功用于酮类与腈类的分子间和分子内还原偶联反应。在室温或回流的中性条件下，已经制备了多种取代模式的α-羟基酮、单环和融合双环的α-羟基酮以及单环的α-氨基醇，产率良好。该方法能够避免生成的α-羟基酮或α-氨基醇的过度还原。还报告了单环α-氨基醇的晶体结构。
• Rhodium-catalyzed addition of arylstannanes to carbon–heteroatom double bond
  作者：Shuichi Oi、Mitsutoshi Moro、Hiroe Fukuhara、Takanori Kawanishi、Yoshio Inoue

  DOI：10.1016/s0040-4020(03)00586-6

  日期：2003.6

  The addition of arylstannanes to the carbon–heteroatom double bond in the presence of a catalytic amount of a cationic rhodium complex ([Rh(cod)(MeCN)2]BF4) was examined. The reactions of aldehydes, α-dicarbonyl compounds, and N-substituted aldimines with the arylstannanes gave corresponding alcohols, α-hydroxy carbonyl compounds, and amines, respectively. An arylrhodium complex generated by the transmetalation

  研究了在催化量的阳离子铑配合物（[Rh（cod）（MeCN）2 ] BF 4）存在下，向碳-杂原子双键中添加了芳基锡烷。醛，α-二羰基化合物和N-取代的亚胺与芳基锡烷的反应分别得到相应的醇，α-羟基羰基化合物和胺。通过芳基锡烷的重金属化反应生成的芳基铑络合物可能是活性催化物质。
• Three-Component Coupling of Acylphosphonates and Two Carbonyl Compounds Promoted by Low-Valent Samariums:  One-Pot Synthesis of β-Hydroxyphosphonates
  作者：Ken Takaki、Yuichiro Itono、Akihiro Nagafuji、Yoji Naito、Tetsuya Shishido、Katsuomi Takehira、Yoshikazu Makioka、Yuki Taniguchi、Yuzo Fujiwara

  DOI：10.1021/jo991357s

  日期：2000.1.1

  Three-component coupling of acylphosphonates and two carbonyl compounds leading to beta-hydroxyphosphonates has been achieved with low-valent samariums. Thus, acylphosphonates reacted with aldehydes in the presence of semicatalytic amounts of samarium metal or SmI2 to give acyloxy-phosphonates in good yields. The second coupling reaction of the acyloxyphosphonates with aldehydes or ketones promoted by SmI2 afforded beta-hydroxyphosphonates instead of olefins. Moreover, these two reactions could be carried out in one pot.