4,4'-[(2SR,3RS)-oxirane-2,3-diyl]dibenzonitrile | 13528-34-2

• 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: 4,4'-[(2SR,3RS)-oxirane-2,3-diyl]dibenzonitrile
• 英文别名: cis-2,3-bis(4-cyanophenyl)oxirane；2,3-bis-(4-cyano-phenyl)-oxirane；cis-1,2-Bis-(4-cyan-phenyl)-ethylenoxid；4-[(2R,3S)-3-(4-cyanophenyl)oxiran-2-yl]benzonitrile
• CAS: 13528-34-2
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: YEMJHBWHZALWPH-IYBDPMFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  60.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4'-[(2SR,3RS)-oxirane-2,3-diyl]dibenzonitrile 、 tert-butyl(dimethyl)(phenylseleno)silane 在 四甲基乙二胺 作用下， 以 二氯甲烷 为溶剂， 反应 96.0h， 生成 (1R,2R)-1,2-bis(4-cyanophenyl)-2-(phenylseleno)ethanol 、 (1S,2S)-1,2-bis(4-cyanophenyl)-2-(phenylseleno)ethanol
  参考文献：
  名称：

  用（苯基硒代）硅烷催化内消旋环氧化合物的不对称开环合成对映体富集的β-羟基硒化物

  摘要：

  的对映选择性开环的第一实施例的内消旋通过使用萨伦（Cr）的络合物作为催化剂进行说明（phenylseleno）硅烷-环氧化物。该去对称化反应构成了合成通用的光学活性β-羟基硒化物的简便方法。

  DOI：

  10.1016/j.tet.2008.01.126
• 作为产物：
  描述：

  cis-4,4'-dicyanostilbene 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成 4,4'-[(2SR,3RS)-oxirane-2,3-diyl]dibenzonitrile
  参考文献：
  名称：

  Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex

  摘要：

  This study describes a C-2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8 '-(Hydroxy-diphenyl-methyl)-10,10,10 ',10 '-tetramethyl-[5,5']bi[6-aza-tricyclo[7.1.1.0(2,7) ]undecyl]-2(7),3,5, 2 '(7 '),3 ',5 '-hexaen-8-yl]-diphenyl-methanol 1 is an effective catalyst in the asymmetric ring opening (ARO) of ineso-epoxides with PhSH and inductions of up to 69% ee. Importantly, there was a correlation between Hammett substituent constants and enantiomeric excesses; the electron-donating substituents at the meta- and para-positions of the substituted stilbene oxides had good enantioselectivity during the epoxide ring opening using PhSH. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.04.030

文献信息

• Unusual Reactivity of Aryl Aldehydes with Triethyl Phosphite and Zinc Bromide: A Facile Preparation of Epoxides, Benzisoxazoles, and α-Hydroxy Phosphonate Esters
  作者：Potharaju Raju、Ganesan Gobi Rajeshwaran、Meganathan Nandakumar、Arasambattu K. Mohanakrishnan

  DOI：10.1002/ejoc.201500332

  日期：2015.6

  A facile preparation of trans-epoxides was achieved by a (EtO)3P–ZnBr2-mediated deoxygenation reaction of the corresponding 2-nitrobenzaldehydes. The sterically hindered analogues of 2-nitrobenzaldehyde underwent a reaction with triethyl phosphite in the presence of ZnBr2 as the catalyst to form benzisoxazoles as the sole product. Under identical conditions, the reactions of electron-rich as well as

  通过相应的 2-硝基苯甲醛的 (EtO)3P-ZnBr2 介导的脱氧反应，可以轻松制备反式环氧化物。2-硝基苯甲醛的空间位阻类似物在作为催化剂的 ZnBr2 存在下与亚磷酸三乙酯发生反应，形成苯并异恶唑作为唯一产物。在相同条件下，富电子和适度缺电子芳醛的反应提供相应的α-羟基膦酸酯。
• P(MeNCH₂CH₂)₃N:  A Highly Selective Reagent for Synthesizing <i>trans</i>-Epoxides from Aryl Aldehydes
  作者：Xiaodong Liu、John G. Verkade

  DOI：10.1021/jo000122+

  日期：2000.7.1

  In contrast to its acyclic analogue P(NMe2)3 (1), which in benzene at room temperature reacts with two aryl aldehyde molecules bearing electron-withdrawing groups to give the corresponding diaryl epoxide as an isomeric mixture (trans/cis ratios: 72/28-51/49), P(MeNCH2CH2)3N (2a) under the same reaction conditions is found to be a highly selective reagent that provides epoxides with trans/cis ratios

  与它的无环类似物P（NMe2）3（1）相比，后者在室温下在苯中与两个带有吸电子基团的芳基醛分子反应，得到相应的二芳基环氧化物，为异构体混合物（反式/顺式比：72 / 28（51/49），P（MeNCH2CH2）3N（2a）在相同的反应条件下被发现是一种高度选择性的试剂，可提供反式/顺式比高达99/1的环氧化物。使用2a时，这些反应更快，因为它的磷原子显然比1中的亲核性更高。因此，发现2a更容易分别与一或两个醛分子形成1：1和1：2加合物。这些加合物显然是产物环氧化物和1a和2a的相应氧化膦形成的中间体。
• Synthesis of enantiomerically enriched β-hydroxy selenides by catalytic asymmetric ring opening of meso-epoxides with (phenylseleno)silanes
  作者：Marcello Tiecco、Lorenzo Testaferri、Francesca Marini、Silvia Sternativo、Francesca Del Verme、Claudio Santi、Luana Bagnoli、Andrea Temperini

  DOI：10.1016/j.tet.2008.01.126

  日期：2008.4

  The first example of the enantioselective ring opening of meso-epoxides by (phenylseleno)silanes using salen(Cr)complexes as catalyst is described. This desymmetrization reaction constitutes a simple and convenient approach to synthetically versatile optically active β-hydroxy selenides.

  的对映选择性开环的第一实施例的内消旋通过使用萨伦（Cr）的络合物作为催化剂进行说明（phenylseleno）硅烷-环氧化物。该去对称化反应构成了合成通用的光学活性β-羟基硒化物的简便方法。
• Enantioselective ring-opening reaction of meso-epoxides with ArSH catalyzed by a C2-symmetric chiral bipyridyldiol-titanium complex
  作者：Yi-Jing Chen、Chinpiao Chen

  DOI：10.1016/j.tetasy.2007.04.030

  日期：2007.6

  This study describes a C-2-symmetric ligand comprising a central bipyridine-pinene-derived core and two functionalized diphenylmethanol subunits. [8 '-(Hydroxy-diphenyl-methyl)-10,10,10 ',10 '-tetramethyl-[5,5']bi[6-aza-tricyclo[7.1.1.0(2,7) ]undecyl]-2(7),3,5, 2 '(7 '),3 ',5 '-hexaen-8-yl]-diphenyl-methanol 1 is an effective catalyst in the asymmetric ring opening (ARO) of ineso-epoxides with PhSH and inductions of up to 69% ee. Importantly, there was a correlation between Hammett substituent constants and enantiomeric excesses; the electron-donating substituents at the meta- and para-positions of the substituted stilbene oxides had good enantioselectivity during the epoxide ring opening using PhSH. (c) 2007 Elsevier Ltd. All rights reserved.