(+/-)-2-(phenylethynyl)oxetane | 41415-69-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (+/-)-2-(phenylethynyl)oxetane
• 英文别名: (dl)-2-(2-phenylethynyl)oxetane；2-(2-Phenylethynyl)oxetane
• CAS: 41415-69-4
• 化学式: C₁₁H₁₀O
• 分子量: 158.2
• InChiKey: NFQBMLBSFVTQBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (+/-)-2-(phenylethynyl)oxetane 在 吡啶 、 lithium aluminium tetrahydride 、 bipyrindine derivative copper 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成
  参考文献：
  名称：

  Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone

  摘要：

  Chiral bipyrindine and biquinoline which have been reported to be efficient Ligands for the construction of chiral copper catalysts, were synthesized enantioselectively by rising Mn-salen catalyzed asymmetric epoxidation as a key step. Enantioselective synthesis of trans-whisky lactone was then achieved by way of enantiospecific ring expansion reaction of oxetane with a chiral copper catalyst bearing the bipyrindine Ligand as a chiral source.

  DOI：

  10.1016/s0040-4020(96)00058-0
• 作为产物：
  描述：

  5-Phenyl-3-(tetrahydro-pyran-2-yloxy)-pent-4-yn-1-ol 在 4-二甲氨基吡啶 、 正丁基锂 、 camphor-10-sulfonic acid 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (+/-)-2-(phenylethynyl)oxetane
  参考文献：
  名称：

  Chiral bipyrindine and biquinoline ligands: Their asymmetric synthesis and application to the synthesis of trans-whisky lactone

  摘要：

  Chiral bipyrindine and biquinoline which have been reported to be efficient Ligands for the construction of chiral copper catalysts, were synthesized enantioselectively by rising Mn-salen catalyzed asymmetric epoxidation as a key step. Enantioselective synthesis of trans-whisky lactone was then achieved by way of enantiospecific ring expansion reaction of oxetane with a chiral copper catalyst bearing the bipyrindine Ligand as a chiral source.

  DOI：

  10.1016/s0040-4020(96)00058-0

文献信息

• Photochemical Functionalization of Heterocycles with EBX Reagents: C−H Alkynylation versus Deconstructive Ring Cleavage**
  作者：Errika Voutyritsa、Marion Garreau、Maroula G. Kokotou、Ierasia Triandafillidi、Jérôme Waser、Christoforos G. Kokotos

  DOI：10.1002/chem.202002868

  日期：2020.11.11

  The development of novel methodologies for the functionalization of saturated heterocycles is highly desirable. Herein, we report a cheap and efficient photochemical method for the C−H functionalization of saturated O‐heterocycles, as well as the deconstructive ring‐cleavage of S‐heterocycles, employing hypervalent iodine alkynylation reagents (ethynylbenziodoxolones, EBX). This photochemical alkynylation

  非常需要开发用于饱和杂环官能化的新方法。本文中，我们报告了一种便宜且有效的光化学方法，用于使用饱和的O-炔基化试剂（乙炔基苯并zio恶唑，EBX）对饱和O-杂环的C-H功能化以及S-杂环的解构环裂解。该光化学炔化反应是利用苯基乙醛酸作为光引发剂，在家用荧光灯的照射下以高至高收率得到相应的产物。当使用O-杂环时，发生了预期的α-C-H炔基化反应。相反，在S-杂环上观察到氧化性开环形成硫代炔烃和醛。
• Enantioselective Synthesis of<i>trans</i>-Whisky Lactone by Using Newly Developed Asymmetric Ring Expansion Reaction of Oxetane as a Key Step
  作者：Katsuji Ito、Miwa Yoshitake、Tsutomu Katsuki

  DOI：10.1246/cl.1995.1027

  日期：1995.11

  A mixture of optically active 3-substituted cis- and trans-tetrahydrofuran-2-carboxylates which was prepared in one step from readily available (±)-2-alkynyloxetane, was converted into trans-whisky lactone (2) in a straightforward manner.

  由容易获得的 (±)-2-炔基氧杂环丁烷一步制备的旋光 3-取代的顺式和反式四氢呋喃-2-羧酸酯的混合物以直接的方式转化为反式威士忌内酯 (2)。
• Enantiopsecific Ring Expansion of Oxetanes: Stereoselective Synthesis of Tetrahydrofurans
  作者：Tsutomu Katsuki、Katsuji Ito、Miwa Yoshitake

  DOI：10.3987/com-95-s35

  日期：——

  Enantiospecific ring expansion of oxetanes to tetrahydrofurans with diazoacetic acid ester was found to be catalyzed by the copper complex of (7R,7'R)-7,7'-di(1-tert-butyldimethylsiloxy-1-methylethyl)-6,6',7,7'-tetrahydro-5H,5'H-2,2'-bi-1,1'-pyrindine (4). For example, the reaction of (R)-2-phenyloxetane of 89% ee and tert-buryl diazoacetate with Cu-4 complex as a catalyst provided (2S,3R)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 92% ee as a major product, while that of (S)-2-phenyloxetane of 85% ee provided (2S,3S)-tert-butyl 3-phenyltetrahydrofuran-2-carboxylate of 93% ee as a major one.
• Regioselective Ring-opening Fluorination of Oxetanes with Silicon Tetrafluoride
  作者：Makoto Shimizu、Shigekazu Kanemoto、Yuko Nakahara

  DOI：10.3987/com-99-s37

  日期：——

  Oxetanes were regioselectively cleaved with silicon tetrafluoride to give gamma-fluoro alcohols in good yields, in which effects of additives and stereoselectivities were investigated.