(-)-(E)-1-cyano-1,2-diphenylcyclopropane | 87421-66-7

• 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: (-)-(E)-1-cyano-1,2-diphenylcyclopropane
• 英文别名: (1S,2S)-1,2-diphenylcyclopropane-1-carbonitrile
• CAS: 87421-66-7
• 化学式: C₁₆H₁₃N
• 分子量: 219.286
• InChiKey: MIVVDTYTHSYGAF-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 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：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(E)-1-cyano-1,2-diphenylcyclopropane 以 苯 为溶剂， 反应 17.0h， 生成 (+)-(Z)-1-氰基-1,2-二苯基环丙烷
  参考文献：
  名称：

  Steric retard of internal rotation in 1-carbomethoxy-1,2-diphenylcyclopropane

  摘要：

  DOI：

  10.1021/jo00171a025
• 作为产物：
  描述：

  trans-1,2-diphenyl-1-cyclopropanecarboxylic acid 在 吡啶 、 氨 、 氯甲酸乙酯 、 三乙胺 、 对甲苯磺酰氯 作用下， 反应 12.17h， 生成 (-)-(E)-1-cyano-1,2-diphenylcyclopropane
  参考文献：
  名称：

  Steric retard of internal rotation in 1-carbomethoxy-1,2-diphenylcyclopropane

  摘要：

  DOI：

  10.1021/jo00171a025

文献信息

• Design and Synthesis of Novel Chiral Dirhodium(II) Carboxylate Complexes for Asymmetric Cyclopropanation Reactions
  作者：Frady G. Adly、Michael G. Gardiner、Ashraf Ghanem

  DOI：10.1002/chem.201504817

  日期：2016.3.1

  the design of dirhodium(II) tetracarboxylates derived from (S)‐amino acid ligands is reported. The approach is founded on tailoring the steric influences of the overall catalyst structure by reducing the local symmetry of the ligand's N‐heterocyclic tether. The application of the new approach has led to the uncovering of [Rh2(S‐tertPTTL)4] as a new member of the dirhodium(II) family with extraordinary

  报道了一种新颖的设计从（S）-氨基酸配体衍生的四羧酸二（二）铑（II）的方法。该方法的基础是通过减少配体的N杂环系链的局部对称性来调整整个催化剂结构的空间影响。新方法的应用已导致的揭露的[Rh 2（小号-叔PTTL）4 ]作为二铑（II）家族在环丙烷化反应非凡选择性的新成员。发现[Rh 2（S - tert PTTL）4 ]的立体选择性与[Rh 2（S‐PTAD）4 ]（ee高达99％以上），其附加优点是可以通过综合方式访问。还讨论了基于X射线结构的相关性以证明观察到的对映体诱导是正当的。
• Reaction of vinyl sulphone with α-metallated nitriles
  作者：Toshio Agawa、Yasuo Yoshida、Mitsuo Komatsu、Yoshiki Ohshiro

  DOI：10.1039/p19810000751

  日期：——

  Vinyl sulphones (1) were subjected to nucleophilic addition by α-lithionitriles (2) and gave cyclized products, 3-oxothian 1,1-dioxides (3) or cyclopropane derivatives (4), in satisfactory yields according to the substituents on the reagents. The cyclopropanation reactions could be extended to the formation of cyclopropyl sulphides (12)–(16) in good yields.

  根据试剂上的取代基，以令人满意的收率，将乙烯基砜（1）通过α-锂离子（2）进行亲核加成，得到环化产物3-氧杂环丁烷1,1-二氧化物（3）或环丙烷衍生物（4）。 。环丙烷化反应可以以高收率扩展到环丙基硫化物（12）-（16）的形成。
• Reactions of Hypervalent Iodonium Alkynyl Triflates with Azides: Generation of Cyanocarbenes
  作者：I. F. Dempsey Hyatt、Mitchell P. Croatt

  DOI：10.1002/anie.201203062

  日期：2012.7.23

  time: Cyanocarbenes have been formed by the reaction of azides with hypervalent iodonium alkynyl triflates (HIATs). Experimental evidence supports the potential intermediacy of an azide‐substituted vinylidene or alkynyl azide, both of which could form a cyanocarbene. Trapping of the vinylidene and cyanocarbene includes OH insertion, dimethyl sulfoxide coordination, and cyclopropanation reactions.

  宝贝，再一次，我好：叠氮化物与高价碘鎓炔基三氟甲磺酸酯（HIAT）的反应形成了氰基甲炔。实验证据支持叠氮化物取代的亚乙烯基或炔基叠氮化物的潜在中间体，两者均可形成氰基卡宾。亚乙烯基和cyanocarbene捕集包括O-  ħ插入，二甲基亚砜协调，和环丙烷的反应。
• A New Stereoselective Synthesis of Cyclopropanes Containing Quaternary Stereocentres via Organocatalytic Michael Addition to Vinyl Selenones
  作者：Francesca Marini、Silvia Sternativo、Francesca Del Verme、Lorenzo Testaferri、Marcello Tiecco

  DOI：10.1002/adsc.200900222

  日期：——

  organocatalytic method for the stereoselective synthesis of highly substituted cyclopropanes is reported. The Michael adducts, generated through the addition of α-substituted cyanoacetates to easily accessible vinyl selenones catalyzed by a bifunctional ureidic catalyst, smoothly cyclize by intramolecular alkylation induced by a de-ethoxycarbonylation process. The one-pot sequence generates cyclopropanes

  报道了一种新型的有机催化方法，用于立体选择性合成高度取代的环丙烷。通过将α-取代的氰基乙酸酯加到由双官能尿素催化剂催化的易于获得的乙烯基硒酮中生成的迈克尔加合物，通过由脱乙氧基羰基化过程诱导的分子内烷基化而平滑地环化。的单釜序列生成环丙烷轴承相邻的叔和季立体中心为单Ž -异构体在较高产率和良好的对映体过量。
• Cyclopropanation of Aryl and Styryl Acetonitriles With Selenium‐Based Dielectrophiles
  作者：Italo Franco Coelho Dias、Giulia Allegrini、Ewelina Wielgus、Józef Drabowicz、Eder João Lenardão、Luana Bagnoli、Claudio Santi、Francesca Marini

  DOI：10.1002/ejoc.202400187

  日期：2024.6.3

  Efficient cyclopropanation reactions of aryl or styrylacetonitriles with vinyl selenones under mild conditions were described. By this approach, synthetically challenging 1‐vinylcyclopropane‐1‐carbonitriles were accessible in good yields. This methodology features the advantage of operational simplicity, broad substrate scope, good functional group tolerance, transition‐metal‐free conditions, mild temperature, and a high level of regio‐ and diastereo‐control.