(1R,2S)-(+)-1,2-diphenyl-cyclopropanecarbaldehyde | 1200806-98-9

• 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: (1R,2S)-(+)-1,2-diphenyl-cyclopropanecarbaldehyde
• 英文别名: (1R,2S)-1,2-diphenylcyclopropane-1-carbaldehyde
• CAS: 1200806-98-9
• 化学式: C₁₆H₁₄O
• 分子量: 222.287
• InChiKey: WNNSIFYTWPKAKC-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.31
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (2-苯基环丙烯-1-基)苯 生成 (1R,2S)-(+)-1,2-diphenyl-cyclopropanecarbaldehyde
  参考文献：
  名称：

  NALESNIK, T. E.;FREUDENBERGER, J. H.;ORCHIN, M., J. ORGANOMET. CHEM., 1982, 236, N 1, 95-100

  摘要：

  DOI：

文献信息

• Synthesis and Reactivity of Sulfamoyl Azides and 1-Sulfamoyl-1,2,3-triazoles
  作者：Jeffrey C. Culhane、Valery V. Fokin

  DOI：10.1021/ol201705k

  日期：2011.9.2

  Sulfamoyl azides are readily generated from secondary amines and a novel sulfonyl azide transfer agent, 2,3-dimethyl-1H-imidazolium triflate. They react with alkynes in the presence of a CuTC catalyst forming 1-sulfamoyl-1,2,3-triazoles. The latter are shelf-stable progenitors of rhodium azavinyl carbenes, versatile reactive intermediates that, among other reactions, readily and asymmetrically add

  磺酰基叠氮化物很容易由仲胺和新型磺酰叠氮化物转移剂 2,3-二甲基-1 H-咪唑鎓三氟甲磺酸盐生成。它们在 CuTC 催化剂存在下与炔烃反应形成 1-氨磺酰基-1,2,3-三唑。后者是铑氮杂乙烯基卡宾的货架稳定前体，是多功能的反应中间体，在其他反应中，很容易和不对称地添加到烯烃中。
• Grimster, Neil; Zhang, Li; Fokin, Valery V., Journal of the American Chemical Society, 2010, vol. 132, p. 2510 - 2511
  作者：Grimster, Neil、Zhang, Li、Fokin, Valery V.

  DOI：——

  日期：——
• Rhodium-Catalyzed Enantioselective Cyclopropanation of Olefins with <i>N</i>-Sulfonyl 1,2,3-Triazoles
  作者：Stepan Chuprakov、Sen Wai Kwok、Li Zhang、Lukas Lercher、Valery V. Fokin

  DOI：10.1021/ja908075u

  日期：2009.12.23

  N-Sulfonyl 1,2,3-triazoles readily form rhodium(II) azavinyl carbenes, which react with olefins to produce cyclopropanes with excellent diastereo- and enantioselectivity and in high yield.
• Reactivity of <i>N</i>-(1,2,4-Triazolyl)-Substituted 1,2,3-Triazoles
  作者：Mikhail Zibinsky、Valery V. Fokin

  DOI：10.1021/ol201949h

  日期：2011.9.16

  Synthetically useful rhodium(II) carbenes were obtained from N-(1,2,4-triazolyl)-substituted 1,2,3-triazoles and Rh(II) carboxylates. The electron-withdrawing 1,2,4-triazolyl group reveals the heretofore unknown reactivity of nonsulfonyl 1,2,3-triazoles, which exhibit the reactivity of diazo compounds. The resulting carbenes provide ready asymmetric access to secondary homoaminocyclopropanes (80-95% ee, dr >20:1) via reactions with olefins and also engage in efficient transannulation reactions with nitriles.