methyl (S)-(+)-2,2-diphenylcyclopropanecarboxylate | 82343-33-7

• 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: methyl (S)-(+)-2,2-diphenylcyclopropanecarboxylate
• 英文别名: methyl-2,2-diphenyl-cyclopropane carboxylate；methyl (1S)-2,2-diphenylcyclopropane-1-carboxylate
• CAS: 82343-33-7
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: RDCBDWDNFBAQJQ-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (S)-(+)-2,2-diphenylcyclopropanecarboxylate 、 phenylmagnesium bromide 以 乙醚 为溶剂， 反应 3.0h， 以64%的产率得到(S)-(+)-1-(diphenylhydroxymethyl)-2,2-diphenylcyclopropane
  参考文献：
  名称：

  Chiral carbenoids: their formation and reactions

  摘要：

  Carbenoids, generated by metalation or halogen-metal exchange reactions, have been prepared from chiral vinyl and cyclopropyl halides. The reactivity and stereochemistry observed in the reaction of these carbenoids has been interpreted as being due to metal-assisted ionization (MAI).

  DOI：

  10.1021/jo00055a004
• 作为产物：
  描述：

  (+)-(S)-methyl 1-bromo-2,2-diphenylcyclopropanecarboxylate 生成 methyl (S)-(+)-2,2-diphenylcyclopropanecarboxylate
  参考文献：
  名称：

  HAZARD, R.;JAOUANNET, S.;RAOUILT, E.;TALLEC, A., NOUV. J. CHIM., 1982, 6, N 6, 325-333

  摘要：

  DOI：

文献信息

• Aza-bis(oxazolines):  New Chiral Ligands for Asymmetric Catalysis
  作者：Martin Glos、Oliver Reiser

  DOI：10.1021/ol005947k

  日期：2000.7.1

  Aza-bis(oxazolines) are introduced as chiral ligands for asymmetric catalysis combining the advantages of easy availability of bis(oxazolines) and backbone variability of aza-semicorrins. Especially, the title ligands could be attached to a polymeric support, which allowed the development of easily recoverable copper(I)-catalysts for asymmetric cyclopropanation reactions.

  引入氮杂双（恶唑啉）作为用于不对称催化的手性配体，结合了易于获得的双（恶唑啉）和氮杂半精蛋白的主链可变性的优点。特别地，标题配体可以连接到聚合物载体上，这允许开发用于不对称环丙烷化反应的易于回收的铜（I）催化剂。
• Synthesis of Polymer Bound Azabis(oxazoline) Ligands and their Application in Asymmetric Cyclopropanations
  作者：Heiko Werner、Clara I. Herrerías、Michael Glos、Anja Gissibl、Jose M. Fraile、Ignacio Pérez、Jose A. Mayoral、Oliver Reiser

  DOI：10.1002/adsc.200505197

  日期：2006.1

  Aza(bisoxazoline) ligands were attached to various polymeric supports and the resulting immobilized ligands were evaluated in copper(I)-catalyzed asymmetric cyclopropanations. The efficiency of these transformations depends greatly on the polymeric support, on the protocol being applied for the immobilization of the ligands, and on the preparation of the catalysts.

  将氮杂（双恶唑啉）配体连接到各种聚合物载体上，并在铜（I）催化的不对称环丙烷化反应中评估所得固定的配体。这些转化的效率在很大程度上取决于聚合物载体，用于固定配体的方案以及催化剂的制备。
• Enantioselective deprotonation of two racemic cyclic carbonyl compounds by a chiral lithium amide
  作者：M.B. Eleveld、H. Hogeveen

  DOI：10.1016/s0040-4039(00)84059-9

  日期：1986.1

  cyclic carbonyl compounds and have been obtained in optical active form (o. y. 46% and 36%, respectively) from the racemic compounds by a deprotonation/protonation sequence using chiral lithium amide . The optical activity of is caused by a difference in the deprotonation rates of the enantiomers.

  环状羰基化合物和从通过使用手性氨基化锂脱质子化/质子化序列中的外消旋化合物光学活性形式已经获得（OY 46％和36％，分别地）。的光学活性是由对映异构体的去质子化速率的差异引起的。
• Modular ligands in asymmetric synthesis. Copper-mediated cyclopropanation
  作者：Dora Tepfenhart、Lionel Moisan、Peter I. Dalko、Janine Cossy

  DOI：10.1016/j.tetlet.2003.12.061

  日期：2004.2

  mediates asymmetric intermolecular cyclopropanations. Complexes derived from (R,R)- or (S,S)-1,1-diphenylethylenediamine, cyclic ketones, and Cu(I) or Cu(II) triflates were compared. The reaction between (−)-menthyl diazoacetate and 1,1-diphenylethylene affords cyclopropane carboxylates in up to 80% yield and with up to 78% de.

  手性咪唑啉/铜催化剂体系有效地介导了不对称的分子间环丙烷化。比较了衍生自（R，R）-或（S，S）-1,1-二苯基乙二胺，环酮和Cu（I）或Cu（II）三氟甲磺酸酯的配合物。（-）-薄荷基重氮乙酸酯与1,1-二苯基乙烯之间的反应以高达80％的收率和高达78％的de产率提供环丙烷羧酸酯。
• Chiral carbenoids: their formation and reactions
  作者：M. Topolski、M. Duraisamy、J. Rachon、J. Gawronski、K. Gawronska、V. Goedken、H. M. Walborsky

  DOI：10.1021/jo00055a004

  日期：1993.1

  Carbenoids, generated by metalation or halogen-metal exchange reactions, have been prepared from chiral vinyl and cyclopropyl halides. The reactivity and stereochemistry observed in the reaction of these carbenoids has been interpreted as being due to metal-assisted ionization (MAI).