2-乙炔基-3-苯基环氧乙烷 | 221129-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-乙炔基-3-苯基环氧乙烷
• 中文别名: L-阿拉伯酸,2,3-脱水-
• 英文名称: 2-ethynyl-3-phenyloxirane
• CAS: 221129-39-1
• 化学式: C₁₀H₈O
• 分子量: 144.173
• InChiKey: VQMLIYNSAGLXAT-UHFFFAOYSA-N

物化性质

• 沸点：
  220.4±39.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-乙炔基-3-苯基环氧乙烷 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以51%的产率得到1-phenylbuta-2,3-dien-1-one
  参考文献：
  名称：

  Double Deprotonation of Acetylenic Oxiranes:  Synthesis of Allenic Ketones through Dilithio Ynenolates

  摘要：

  The double deprotonation of acetylenic oxiranes gives allenic ketones through the 1,2-H or 1,2-Ar shift on the transient oxiranyl dianion intermediates. The resulting dilithium ynenolates give allenic ketones upon hydrolysis or can be quenched with various electrophiles.

  DOI：

  10.1021/ol048630j
• 作为产物：
  描述：

  3-chloro-4-phenyl-1-(trimethylsilyl)but-1-yn-4-ol 在 potassium fluoride 、 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-乙炔基-3-苯基环氧乙烷
  参考文献：
  名称：

  Metalation of 3-trimethylsilyl propargyl chloride: A stereoselective access to trans-propargylic oxiranes

  摘要：

  The metalation of 3-trimethylsilyl-1-chloroprop-2-yne and the subsequent reaction with aldehydes affords stereospecifically anti-chlorohydrins which give after treatment with potassium fluoride and NaOH propargylic epoxides with good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)80023-3

文献信息

• Three-Carbon Homologation of Diorganozincs with Lithiated Acetylenic Epoxides
  作者：Aurélien Denichoux、Laurent Debien、Mathieu Cyklinsky、Malika Kaci、Fabrice Chemla、Franck Ferreira、Alejandro Pérez-Luna

  DOI：10.1021/jo302128n

  日期：2013.1.4

  Reaction of dialkylzincs with lithiated acetylenic epoxides is described to give zincates that undergo a 1,2-metallate rearrangement by an anti-SN2′ pathway. This rearrangement occurs with the transfer of an alkyl or a silyl group affording allenylzinc intermediates. Allenic and/or homopropargylic alcohols are obtained upon hydrolysis. Quenching the reaction mixture with aldehydes or ketones is shown

  描述了二烷基锌与锂化的炔属环氧化物的反应以通过反-S N 2'途径产生经历1，2-金属盐重排的锌酸盐。这种重排通过烷基或甲硅烷基的转移发生而得到烯丙基锌中间体。烯丙和/或均丙醇在水解时获得。显示用醛或酮淬灭反应混合物以立体选择性方式获得2-炔基-1,3-二醇。
• Asymmetric Oxidative Lactonization of Enynyl Boronates
  作者：Kezhuo Zhang、Chenchen Li、Yining Jia、Wanxiang Zhao

  DOI：10.1002/anie.202209004

  日期：2022.10.10

  We present herein the first oxidation of enynyl boronates for the synthesis of γ-lactones, including spiro-, and fused-butanolides as well as butenolides that are prevalent in nature products and bioactive molecules. The asymmetric version of this oxidation was also achieved in the presence of chiral ketone and Oxone. This process successively involves the oxidation of C(sp)−B bond, the epoxidation

  我们在此提出了用于合成γ-内酯的烯基硼酸酯的第一次氧化，包括螺环和稠合丁内酯以及在天然产物和生物活性分子中普遍存在的丁烯内酯。这种氧化的不对称形式也在手性酮和 Oxone 的存在下实现。该过程依次涉及 C(sp)-B 键的氧化、C-C 双键的环氧化和内酯化。
• Use of α-chlorosulfides in indium promoted CC couplings: easy entry into the stereoselective formation of epoxy alkynes
  作者：Gregory Engstrom、Meisha Morelli、Carolyn Palomo、Thomas Mitzel

  DOI：10.1016/s0040-4039(99)01152-1

  日期：1999.8

  The use of alpha-chlorosulfide compounds to control stereoselectivity in indium promoted C-C couplings occurs smoothly at room temperature under aqueous and mixed aqueous/organic conditions. Use of the halide to control syn/anti ratios simplifies the indium promoted coupling with respect to earlier studies and is used to gain entry into stereocontrolled epoxy alkynes in good yields. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Metalation of 3-trimethylsilyl propargyl chloride: A stereoselective access to trans-propargylic oxiranes
  作者：Fabrice Chemla、Nicolas Bernard、Jean F. Normant

  DOI：10.1016/s0040-4039(98)80023-3

  日期：1999.1

  The metalation of 3-trimethylsilyl-1-chloroprop-2-yne and the subsequent reaction with aldehydes affords stereospecifically anti-chlorohydrins which give after treatment with potassium fluoride and NaOH propargylic epoxides with good to excellent yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Double Deprotonation of Acetylenic Oxiranes:  Synthesis of Allenic Ketones through Dilithio Ynenolates
  作者：Aurélien Denichoux、Franck Ferreira、Fabrice Chemla

  DOI：10.1021/ol048630j

  日期：2004.9.1

  The double deprotonation of acetylenic oxiranes gives allenic ketones through the 1,2-H or 1,2-Ar shift on the transient oxiranyl dianion intermediates. The resulting dilithium ynenolates give allenic ketones upon hydrolysis or can be quenched with various electrophiles.