2,3-diphenylbutan-1-ol | 108774-24-9

• 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: 2,3-diphenylbutan-1-ol
• 英文别名: (2S*,3R*)-2,3-diphenylbutan-1-ol；(+/-)-erythro-2,3-diphenyl-butan-1-ol；(2S,3R)-2,3-diphenylbutan-1-ol
• CAS: 108774-24-9
• 化学式: C₁₆H₁₈O
• 分子量: 226.318
• InChiKey: MDWBXEKUUFZPLX-BBRMVZONSA-N

物化性质

• 沸点：
  331.8±11.0 °C(Predicted)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2,3-diphenylbutan-1-ol 在 吡啶 、 硫酸 、 溶剂黄146 、 N,N-二甲基甲酰胺 作用下， 生成 3,4-diphenyl-valeric acid
  参考文献：
  名称：

  Five- vs. Six-membered Ring Formation in Acid-catalyzed Cyclizations. II. 3,4-Diphenylvaleric Acid and 2,3-Diphenylglutaric Acid^1,2

  摘要：

  DOI：

  10.1021/ja01556a050
• 作为产物：
  描述：

  D-erythro-2,3-diphenyl-butyric acid 在 lithium aluminium tetrahydride 、 乙醚 作用下， 生成 2,3-diphenylbutan-1-ol
  参考文献：
  名称：

  Five- vs. Six-membered Ring Formation in Acid-catalyzed Cyclizations. II. 3,4-Diphenylvaleric Acid and 2,3-Diphenylglutaric Acid^1,2

  摘要：

  DOI：

  10.1021/ja01556a050

文献信息

• Ni-Catalyzed Arylboration of Unactivated Alkenes: Scope and Mechanistic Studies
  作者：Stephen R. Sardini、Alison L. Lambright、Grace L. Trammel、Humair M. Omer、Peng Liu、M. Kevin Brown

  DOI：10.1021/jacs.9b03991

  日期：2019.6.12

  unactivated monosubstituted, 1,1-disubstituted, and trisubstituted alkenes is disclosed. The reaction is notable in that it converts highly substituted alkenes, aryl bromides, and diboron reagents to products that contain a quaternary carbon and a synthetically versatile carbon-boron bond with control of stereoselectivity and regioselectivity. In addition, the method is demonstrated to be useful for the

  公开了一种未活化的单取代、1,1-二取代和三取代烯烃的Ni催化芳基硼化反应的方法。该反应的值得注意之处在于，它将高度取代的烯烃、芳基溴和二硼试剂转化为含有季碳和合成通用碳硼键的产物，并控制立体选择性和区域选择性。此外，该方法被证明可用于合成饱和氮杂环，这是药物化合物中的重要基序。最后，由于所表现出的不寻常的反应性，我们通过计算和实验技术研究了反应的机理细节。
• Catalytic Intermolecular Tail-to-Tail Hydroalkenylation of Styrenes with α Olefins: Regioselective Migratory Insertion Controlled by a Nickel/N-Heterocyclic Carbene
  作者：Chun-Yu Ho、Lisi He

  DOI：10.1002/anie.201001849

  日期：2010.11.22

  first single‐operation, highly selective intermolecular tail‐to‐tail hetero‐hydroalkenylation from two readily available monosubstituted alkenes is described (see scheme; IPr=1,3‐Bis(2,6‐di‐isopropylphenyl)imidazol‐2‐ylidene). The reaction is catalyzed by the proposed [(IPr)NiH]OTf species. The method allows the use of more common and structurally diverse α olefins as substrates, which were previously

  使头或它的尾巴：第一单操作中，高选择性的分子间尾对尾杂hydroalkenylation从两个容易获得单取代的烯烃中描述（参见方案; IPR = 1,3-双（2,6-二-异丙基苯基）咪唑-2-亚丙基。该反应由提出的[（IPr）NiH] OTf物种催化。该方法允许使用更常见且结构上不同的α-烯烃作为底物，其先前与已知方法不相容。
• Alkyl Ethers as Traceless Hydride Donors in Brønsted Acid Catalyzed Intramolecular Hydrogen Atom Transfer
  作者：Dhika Aditya Gandamana、Bin Wang、Ciputra Tejo、Benoit Bolte、Fabien Gagosz、Shunsuke Chiba

  DOI：10.1002/anie.201801953

  日期：2018.5.22

  A new protocol for the deoxygenation of alcohols and the hydrogenation of alkenes under Brønsted acid catalysis has been developed. The method is based on the use of either a benzyl or isopropyl ether as a traceless hydrogen‐atom donor, and involves an intramolecular hydride transfer as a key step, which is achieved in a regio‐ and stereoselective manner.

  已经开发了在布朗斯台德酸催化下醇的脱氧和烯烃的氢化的新方案。该方法基于使用苄基或异丙基醚作为无痕氢原子供体，并且涉及分子内氢化物转移作为关键步骤，这是通过区域和立体选择性方式实现的。
• Stereoselective migration of sterically hindered organoboranes in cyclic and acyclic systems. A stereoselective allylic C–H activation reaction
  作者：Eike Hupe、Dmitri Denisenko、Paul Knochel

  DOI：10.1016/j.tet.2003.09.043

  日期：2003.11

  The thermal migration of cyclic and acyclic organoboranes were studied. In most cases, a stereoselective 1,2-dyotropic migration was observed, allowing the stereocontrol of three contiguous chiral centers. Scope and limitations of this thermal migration are presented.

  研究了环状和非环状有机硼烷的热迁移。在大多数情况下，可以观察到立体选择性的1,2-二向同性迁移，从而可以立体控制三个连续的手性中心。介绍了这种热迁移的范围和局限性。
• Enantioselective α-Arylation of Aldehydes via the Productive Merger of Iodonium Salts and Organocatalysis
  作者：Anna E. Allen、David W. C. MacMillan

  DOI：10.1021/ja2008906

  日期：2011.3.30

  The enantioselective alpha-arylation of aldehydes has been accomplished using diaiyliodonium salts and a combination of copper and organic catalysts. These mild catalytic conditions provide a new strategy for the enantioselective construction and retention of enolizable alpha-formyl benzylic stereocenters, a valuable synthon for the production of medicinal agents. As one example, this new asymmetric protocol has been applied to the rapid synthesis of (S)-ketoprofen, a commercially successful oral and topical analgesic.