(2R,3R)-2-(2-chlorophenyl)-3-phenyloxirane

• 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: (2R,3R)-2-(2-chlorophenyl)-3-phenyloxirane
• 英文别名: trans-(2R,3R)-2-(2-chlorophenyl)-3-phenyloxirane；trans-2-(o-chlorophenyl)-3-phenyloxirane
• 化学式: C₁₄H₁₁ClO
• 分子量: 230.694
• InChiKey: RGARPKICQJCXPW-ZIAGYGMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  (2R,3R)-2-(2-chlorophenyl)-3-phenyloxirane 在 Amberlist 15 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 20.0h， 以50%的产率得到
  参考文献：
  名称：

  A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

  摘要：

  Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.039
• 作为产物：
  描述：

  (1R,4R,5R,6R)-6-benzyl-4,7,7-trimethyl-6-thioniabicyclo[3.2.1]octane trifluoromethanesulfonate 、 2-氯苯甲醛 在 potassium hydroxide 作用下， 以 乙腈 、 叔丁醇 为溶剂， 以60%的产率得到(2R,3R)-2-(2-chlorophenyl)-3-phenyloxirane
  参考文献：
  名称：

  A mild access to chiral syn 1,2-diaryl glycols by stereoselective ring opening of ortho substituted trans 2,3-diaryl-oxiranes using Amberlyst 15 in H2O/THF system

  摘要：

  Amberlyst 15 was an efficient and green catalyst for the reaction of 2,3-diaryloxiranes with H2O in organic co-solvent to prepare glycols in high yield. Ortho substituted trans 2,3-diaryloxiranes afforded the corresponding syn glycols stereo- and enantiospecifically. Stereoselectivity appeared related to the coordination ability of the substituents, irrespective of their electronic properties. Indeed o-OCH3 and o-OBn substituted syn glycols were obtained in high stereochemical ratios (6/1 and 10/1, respectively), and o-OTIPS and o-NO2 substituted ones were obtained as exclusive products, with the same ee of the parent epoxides. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.06.039

文献信息

• Chiral Macrocyclic Organocatalysts for Kinetic Resolution of Disubstituted Epoxides with Carbon Dioxide
  作者：Tadashi Ema、Maki Yokoyama、Sagiri Watanabe、Sota Sasaki、Hiromi Ota、Kazuto Takaishi

  DOI：10.1021/acs.orglett.7b01838

  日期：2017.8.4

  Among chiral macrocycles 1 synthesized, 1m with the 3,5-bis(trifluoromethyl)phenylethynyl group was the best organocatalyst for the enantioselective synthesis of cyclic carbonates from disubstituted or monosubstituted epoxides and CO2. The X-ray crystal structure of 1m revealed a well-defined chiral cavity with multiple hydrogen-bonding sites that is suitable for the enantioselective activation of

  在合成的手性大环化合物1中，具有3,5-双（三氟甲基）苯基乙炔基的1m是从二取代或单取代的环氧化物和CO 2对映选择性合成环状碳酸酯的最佳有机催化剂。1m的X射线晶体结构揭示了一个明确定义的手性腔，带有多个氢键位，适用于环氧化物的对映选择性活化。提议的催化循环得到DFT计算的支持。
• Domino Processes of Arynes Reacting with Three Classes of Nucleophiles for Organic Syntheses
  作者：Jih Ru Hwu、Avijit Panja、Nitesh K. Gupta、Yu‐Chen Hu、Kui‐Thong Tan、Chun‐Cheng Lin、Kuo‐Chu Hwang、Ming‐Hua Hsu、Wen‐Chieh Huang、Shwu‐Chen Tsay

  DOI：10.1002/ejoc.202001499

  日期：2021.1.26

  Arynes are utilized in the syntheses of 1,2‐dihydroquinolines, epoxides, and phenolic ethers involving Diels‐Alder, Johnson‐Corey‐Chaykovsky, and Claisen‐type rearrangement reactions, respectively, through three different domino processes

  炔烃通过三种不同的多米诺过程分别用于Diels-Alder，Johnson-Corey-Chaykovsky和Claisen型重排反应的1,2-二氢喹啉，环氧化物和酚醚的合成中
• A New Synthesis of trans-2,3-Diaryloxiranes and 2-(1H-Benzo[d][1,2,3]-[nl]triazol-1-yl)-1-arylethanols via the Reactions of 1-Benzyl-3-methylbenzo-[nl]triazolium Ylide with Aryl Aldehydes
  作者：Xiaohui Xiao、Daqin Lin、Shuitian Tong、Hailan Mo

  DOI：10.1055/s-0031-1289555

  日期：2011.12

  1-Benzyl-3-methylbenzotriazolium ylide was formed by the reaction of 1-benzyl-3-methylbenzotriazolium iodide with t-BuOK. Subsequently it reacted with various aryl aldehydes to give the corresponding trans-2,3-diaryloxiranes and 2-(1H-benzo-[d][1,2,3]triazol-1-yl)-1-arylethanols in moderate to high yields.

  1-Benzyl-3-methylbenzotriazolium ylide 是由 1-Benzyl-3-methylbenzotriazolium iodide 与 t-BuOK 反应生成的。随后，它与各种芳基醛反应，得到相应的反式-2,3-二芳基环氧乙烷和 2-(1H-苯并-[d][1,2,3]三唑-1-基)-1-芳基乙醇，收率从中等到较高。
• A New Chiral Organosulfur Catalyst for Highly Stereoselective Synthesis of Epoxides
  作者：Yuan Gui、Jian Li、Chang-Shan Guo、Xin-Liang Li、Zhi-Feng Lu、Zhi-Zhen Huang

  DOI：10.1002/adsc.200800453

  日期：2008.11.3

  A new chrial organosulfide was synthesized through an unexpected Wagner–Meerwein rearrangement. This organosulfide could catalyze the epoxidation reaction of various aromatic aldehydes smoothly with benzyl bromide to give trans-diaryl epoxides in satisfactory yields (60–84%) with excellent diastereoselectivities (trans:cis=95:5–100:0) and good to excellent enantioselectivities (86–96% ee).

  通过意外的Wagner-Meerwein重排合成了一种新的Charial有机硫化物。这种有机硫化物可以顺利地催化各种芳族醛与苄基溴的环氧化反应，以令人满意的非对映选择性（反式：顺式= 95：5–100：0）以令人满意的收率（60–84％）得到反式-二芳基环氧化物。对映选择性（86–96％ee）。
• New Camphor-Derived Selenonium Ylides: Enantioselective Synthesis of Chiral Epoxides
  作者：Xin-Liang Li、Yi Wang、Zhi-Zhen Huang

  DOI：10.1071/ch05157

  日期：——

  selenonium salts 3 as the precursors of two new chiral selenonium ylides 4 can be synthesized stereoselectively from natural d-camphor in good yields. It is found that the reaction of the selenonium salt 3b, an aldehyde, and potassium tert-butoxide can take place smoothly in ‘one-pot’ via the formation of selenonium ylide 4b, to give chiral trans-diaryl epoxides 5 in good yields with good diastereoselectivities

  作为两种新的手性硒叶立德 4 的前体的光学纯硒盐 3 可以由天然 d-樟脑以高收率立体选择性合成。发现硒盐 3b、醛和叔丁醇钾的反应可以通过形成硒内鎓 4b 在“一锅”中顺利进行，从而以良好的收率得到手性反式二芳基环氧化物 5良好的非对映选择性和对映选择性。