(S)-(-)-1-phenyl-1-benzyloxycarbonylaminoprop-2-ene | 177171-67-4

• 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: (S)-(-)-1-phenyl-1-benzyloxycarbonylaminoprop-2-ene
• 英文别名: benzyl N-[(1S)-1-phenylprop-2-enyl]carbamate
• CAS: 177171-67-4
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: WSVSTSSSGDKYCW-INIZCTEOSA-N

物化性质

• 熔点：
  67-68 °C
• 沸点：
  426.6±44.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-phenyl-1-benzyloxycarbonylaminoprop-2-ene 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) potassium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 (S)-(-)-N-benzyloxycarbonyl-2-phenyl-2,5-dihydropyrrole
  参考文献：
  名称：

  Iridium(I)-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Amidation of Substituted Allyl Benzyl Imidodicarbonates

  摘要：

  The first Ir(I)-catalyzed decarboxylative allylic amidation of allyl benzyl imidodicarbonates is described. The reaction requires Ir(I), chiral phosphoramidite ligand, and DBU as well as proton sponge, and proceeds with excellent regio- and enantioselectivities to afford the branched 1-(aryl/alkyl)-1-benzyloxycarbonylaminoprop-2-ene in good to excellent yields. The scope, mechanism, and synthetic applications of the developed catalytic reaction are discussed.

  DOI：

  10.1021/ja067966g
• 作为产物：
  描述：

  benzyloxycarbonyl isocyanate 在 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 chiral phosphoramidite ligand 1,8-双二甲氨基萘 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-(-)-1-phenyl-1-benzyloxycarbonylaminoprop-2-ene
  参考文献：
  名称：

  Iridium(I)-Catalyzed Regio- and Enantioselective Decarboxylative Allylic Amidation of Substituted Allyl Benzyl Imidodicarbonates

  摘要：

  The first Ir(I)-catalyzed decarboxylative allylic amidation of allyl benzyl imidodicarbonates is described. The reaction requires Ir(I), chiral phosphoramidite ligand, and DBU as well as proton sponge, and proceeds with excellent regio- and enantioselectivities to afford the branched 1-(aryl/alkyl)-1-benzyloxycarbonylaminoprop-2-ene in good to excellent yields. The scope, mechanism, and synthetic applications of the developed catalytic reaction are discussed.

  DOI：

  10.1021/ja067966g

文献信息

• Iridium(I)-Catalyzed Stereospecific Decarboxylative Allylic Amidation of Chiral Branched Benzyl Allyl Imidodicarboxylates
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1021/ol702115h

  日期：2007.11.1

  Ir(I)-catalyzed decarboxylative allylic amidation of chiral branched benzyl allyl imidodicarboxylates has been shown to proceed with complete retention of enantiomeric purity and configuration. The transformation is stereospecific and appears to be quite general, accommodating a wide range of R groups.

  已显示手性支化的苄基烯丙基亚氨基二羧酸二甲酯的Ir（I）催化的脱羧烯丙基酰胺化反应可完全保留对映体的纯度和构型。该转化是立体特异性的，并且看起来是相当普遍的，可容纳各种各样的R基团。
• Iridium(I)-catalyzed regio- and enantioselective allylic amidation
  作者：Om V. Singh、Hyunsoo Han

  DOI：10.1016/j.tetlet.2007.08.009

  日期：2007.10

  Ir(I)-catalyzed intermolecular allylic amidation of ethyl allylic carbonates with soft nitrogen nucleophiles under completely "salt-free" conditions is described. A combination of [Ir(COD)Cl](2), a chiral phosphoramidite ligand L*, and DBU as a base in THF effects the reaction. The reaction appears to be quite general, accommodating a wide variety of R-groups and soft nitrogen nucleophiles, and proceeds

  描述了在完全“无盐”条件下 Ir(I)-催化的烯丙基碳酸酯与软氮亲核试剂的分子间烯丙基酰胺化。[Ir(COD)Cl](2)、手性亚磷酰胺配体 L* 和 DBU 作为 THF 中的碱的组合会影响反应。该反应似乎非常普遍，可容纳多种 R-基团和软氮亲核试剂，并以优异的区域和对映选择性进行，以提供支链 N-保护的烯丙胺。所开发的反应可方便地用于 Boc 保护的 α-和β-氨基酸以及 (-)-胞嘧啶的不对称合成。