cis-3,4-diphenyl-γ-butyrolactone | 20453-83-2

• 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: cis-3,4-diphenyl-γ-butyrolactone
• 英文别名: cis-4,5-diphenyldihydrofuran-2(3H)-one；(4S,5S)-4,5-diphenyloxolan-2-one
• CAS: 20453-83-2；53861-52-2；69573-46-2；145279-07-8；147599-28-8；147599-29-9；147599-30-2
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: HSIFUOWGIIPHFW-GOEBONIOSA-N

物化性质

• 沸点：
  410.6±45.0 °C(Predicted)
• 密度：
  1.164±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Stilbene oxide 在 盐酸 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 30.0h， 生成 cis-3,4-diphenyl-γ-butyrolactone
  参考文献：
  名称：

  Mandel'shtam, T. V.; Kolesova, S. V.; Polina, T. V., Journal of Organic Chemistry USSR (English Translation), 1980, vol. 16, p. 1024 - 1031

  摘要：

  DOI：

文献信息

• Silyl Phosphites. XVIII. Versatile Utility of α-(Trimethylsilyloxy)alkylphosphonates as Key Intermediates for Transformation of Aldehydes into Several Carbonyl Derivatives
  作者：Mitsuo Sekine、Masashi Nakajima、Akiko Kume、Akio Hashizume、Tsujiaki Hata

  DOI：10.1246/bcsj.55.224

  日期：1982.1

  trimethylsilyl phosphite (DTMSP) with aldehydes were converted, by treatment with lithium diisopropylamide (LDA) followed by the successive alkylation and alkaline hydrolysis, to carbonyl derivatives involving aldehydes, unsymmetrical ketones, β,γ-unsaturated ketones, and carboxylic acids. β-Substituted carboxylic esters and γ-substituted lactones were prepared by use of the carbonyl addition compounds of DTMSP

  通过用二异丙基氨基锂 (LDA) 处理，然后连续烷基化和碱水解，将二乙基三甲基甲硅烷基亚磷酸酯 (DTMSP) 与醛的羰基加成化合物转化为涉及醛、不对称酮、β,γ-不饱和酮和羧酸的羰基衍生物酸。利用DTMSP的羰基加成化合物与α,β-不饱和醛制备β-取代羧酸酯和γ-取代内酯。
• MnO₂-promoted carboesterification of alkenes with anhydrides: a facile approach to γ-lactones
  作者：Lihuan Wu、Zhenming Zhang、Jianhua Liao、Jianxiao Li、Wanqing Wu、Huanfeng Jiang

  DOI：10.1039/c5cc08867d

  日期：——

  A new radical cyclization method for the formation of C(sp³)–C(sp³) and C–O bonds via MnO₂-promoted alkene carboesterification with anhydrides is developed.

  一种新的基于锰促进的烯烃碳酯化反应的C(sp3)-C(sp3)和C-O键的放射状环化方法被开发出来。
• Rh-catalyzed Addition of β-Carbonyl Pinacol Alkylboronates to Aldehydes: Asymmetric Synthesis of γ-Butyrolactones
  作者：Changwan Zhang、Jaesook Yun

  DOI：10.1021/ol401468v

  日期：2013.7.5

  The rhodium-catalyzed 1,2-addition of chiral benzylic secondary alkylboronic esters with a coordinating carbonyl group to aldehydes was demonstrated with high levels of enantiospecificity. Pinacol boronic ester derivatives can be employed directly for the addition in the presence of KHF2 without the use of corresponding trifluoroborate salts where retention of the configuration was observed. Enantiomerically

  铑与手性苄基仲烷基硼酸酯的铑催化1，2-加成反应后，对映体的对映体特异性很高。品那可硼酸酯衍生物可以在KHF 2存在下直接用于加成反应，而无需使用相应的三氟硼酸盐，因为在这种情况下观察到了构型的保留。以良好的产率合成了对映体富集的β，γ-二芳基取代的γ-丁内酯。
• Carbene catalyzed umpolung of α,β-enals: a reactivity study of diamino dienols vs. azolium enolates, and the characterization of advanced reaction intermediates
  作者：Veera Reddy Yatham、Jörg-M. Neudörfl、Nils E. Schlörer、Albrecht Berkessel

  DOI：10.1039/c5sc01027f

  日期：——

  in 2004, N-heterocyclic carbene catalyzed conjugate Umpolung reactions of [small alpha],[small beta]-enals have been postulated to involve the formation of diamino dienols ("homoenolates") and/or azolium...

  自从Bode和Glorius在2004年发现它们以来，已假定N-杂环卡宾催化的小α，小β-烯醛的共轭Umpolung反应涉及二氨基二烯醇（“均烯酸酯”）和/或azo的形成。 ..
• Activation of carbonyl beta-carbons for chemical transformations
  申请人：Nanyang Technological University

  公开号：US11306097B2

  公开（公告）日：2022-04-19

  The present invention relates to a method for synthesizing a compound of Formula (I) as defined herein, comprising: (i) activating a compound of Formula (II) as defined herein, by reacting said compound of Formula (II) with a compound of Formula (III) as defined herein, in the presence of a base, to obtain a compound of Formula (IV) as defined herein; and (ii) reacting the compound of Formula (IV) with an electrophile to obtain the compound of Formula (I). The present invention further relates to the organocatalysts used in the described methods and their respective uses.

  本发明涉及一种合成式（I）化合物的方法 的方法，包括： (i) 活化式（II）化合物 将所述式 (II) 化合物与式 (III) 化合物反应，得到如本文所定义的化合物 如本文所定义，在碱存在下，得到式（IV）化合物 如本文所定义；以及(ii)使式(IV)化合物与亲电子体反应，得到式(I)化合物。本发明进一步涉及所述方法中使用的有机催化剂及其各自的用途。