3-羟基-2,2-二甲基-1,5-二苯基-1-戊酮 | 82105-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-羟基-2,2-二甲基-1,5-二苯基-1-戊酮
• 英文名称: 3-hydroxy-2,2-dimethyl-1,5-diphenylpentan-1-one
• 英文别名: 3-hydroxy-2,2-dimethyl-1,5-diphenyl-1-pentanone
• CAS: 82105-30-4
• 化学式: C₁₉H₂₂O₂
• 分子量: 282.382
• InChiKey: YEJLPZIZBGAKHT-UHFFFAOYSA-N

物化性质

• 沸点：
  448.4±38.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  异丁酰苯 在 indium (III) iodide 、 二甲基苯基硅烷 、 三乙胺 、 sodium iodide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 2.0h， 生成 3-羟基-2,2-二甲基-1,5-二苯基-1-戊酮
  参考文献：
  名称：

  Direct Use of Esters in the Mukaiyama Aldol Reaction: A Powerful and Convenient Alternative to Aldehydes

  摘要：

  An indium triiodide catalyst promoted the direct transformation from esters to beta-hydroxycarbonyl compounds using hydrosilanes and silyl enolates by a one-stage process. Various esters were applicable, and the high chemoselectivity of this system brings compatibility to many functional groups: alkenyl, alkynyl, chloro, and hydroxy.

  DOI：

  10.1021/ol3001443

文献信息

• Organometallic reactions in aqueous media — Bismuth-mediated crossed aldol type reactions
  作者：Yoon Joo Lee、Tak Hang Chan

  DOI：10.1139/v03-142

  日期：2003.11.1

  Bismuth metal, upon activation by zinc fluoride, can effect the crossed aldol reaction between α-bromocarbonyl compounds and aldehydes in aqueous media. The reaction was found to be regiospecific and syn-diastereoselective.Key words: bismuth, zinc fluoride, aldol reaction, regioselectivity, aqueous media.

  铋金属，在锌氟化物的激活下，可以在水介质中促进α-溴羰基化合物和醛之间的交叉Aldol反应。发现该反应具有区域选择性和syn-立体选择性。关键词：铋、锌氟化物、Aldol反应、区域选择性、水介质。
• Stereoselective Crossed Aldol Reaction via Boron Enolates Generated from α-Iodo Ketones and 9-Borabicyclo[3.3.1]nonane
  作者：Teruaki Mukaiyama、Tomofumi Takuwa、Keiko Yamane、Shouhei Imachi

  DOI：10.1246/bcsj.76.813

  日期：2003.4

  2-iodo-1-(4-methoxyphenyl)propan-1-one, 2-iodopentan-3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one and 1-iodo-4-phenylbutan-2-one with 9-borabicyclo[3.3.1]nonane (9-BBN). Aldols were produced in good yields with good to high diastereoselectivities by subsequent reaction of boron enolates thus formed with various aldehydes. Several boron enolates derived

  硼烯醇化物是通过处理各种 α-碘酮如 2-iodo-1-phenylpropan-1-one、2-iodo-1-(4-methoxyphenyl)propan-1-one、2-iodopentan- 3-one, 2-iodo-2-methyl-1-phenylpropan-1-one, 3,4-dihydro-2-iodo-1(2H)-naphthalenone, 2-iodo-1-phenylethan-1-one 和 1 -iodo-4-phenylbutan-2-one 与 9-borabicyclo[3.3.1]nonane (9-BBN)。通过由此形成的硼烯醇化物与各种醛的后续反应，以良好的收率和良好至高的非对映选择性生产了羟醛。通过蒸馏成功分离了几种衍生自 α-碘酮和频哪醇硼烷的硼烯醇化物，但产率相当适中。
• A NEW METHOD FOR THE REGIO- AND STEREOSELECTIVE SYNTHESIS OF ALDOLS FROM α-BROMOKETONE AND CARBONYL COMPOUNDS BY USING METALLIC TIN
  作者：Taira Harada、Teruaki Mukaiyama

  DOI：10.1246/cl.1982.467

  日期：1982.4.5

  Tin(II) enolates, generated in situ by the oxidative addition of α-bromoketones to metallic tin, react with a variety of carbonyl compounds under mild conditions to give the corresponding aldols in good yields. In the case of reactions of the enolate resulted from α-substituted α-bromoketone with aldehydes, remarkably high erythro-selectivities are attained.

  锡 (II) 烯醇化物通过 α-溴酮与金属锡的氧化加成原位生成，在温和条件下与各种羰基化合物反应，以良好的收率得到相应的醛醇。在由 α-取代的 α-溴酮与醛产生的烯醇反应的情况下，获得了非常高的赤型选择性。
• HARADA, TAIRA;MUKAIYAMA, TERUAKI, CHEM. LETT., 1982, N 4, 467-470
  作者：HARADA, TAIRA、MUKAIYAMA, TERUAKI

  DOI：——

  日期：——