methyl (4R)-4-(2,3-dihydro-1H-indol-1-yl)-2-nitro-4-phenylbutanoate | 1036637-41-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (4R)-4-(2,3-dihydro-1H-indol-1-yl)-2-nitro-4-phenylbutanoate
• 英文别名: methyl (4R)-4-(2,3-dihydroindol-1-yl)-2-nitro-4-phenylbutanoate
• CAS: 1036637-41-8
• 化学式: C₁₉H₂₀N₂O₄
• 分子量: 340.379
• InChiKey: KQAMHZWHRMQGRK-QNSVNVJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (4R)-4-(2,3-dihydro-1H-indol-1-yl)-2-nitro-4-phenylbutanoate 在 lithium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 48.0h， 以88%的产率得到1-[(1R)-3-nitro-1-phenylpropyl]indoline
  参考文献：
  名称：

  Boronate Urea Activation of Nitrocyclopropane Carboxylates

  摘要：

  Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks In good yields. Standard manipulations allow access to a wide range of valuable compounds from the ring-opened products with direct applications in bioactive target synthesis.

  DOI：

  10.1021/ol202873d
• 作为产物：
  描述：

  methyl (1R,2S)-1-nitro-2-phenylcyclopropanecarboxylate 、 吲哚啉 在 nickel(II) perchlorate hexahydrate 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以94%的产率得到methyl (4R)-4-(2,3-dihydro-1H-indol-1-yl)-2-nitro-4-phenylbutanoate
  参考文献：
  名称：

  A Mild Procedure for the Lewis Acid-Catalyzed Ring-Opening of Activated Cyclopropanes with Amine Nucleophiles

  摘要：

  The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine.

  DOI：

  10.1021/ol8009286

文献信息

• Asymmetric Rh(II)-Catalyzed Cyclopropanation of Alkenes with Diacceptor Diazo Compounds: <i>p</i>-Methoxyphenyl Ketone as a General Stereoselectivity Controlling Group
  作者：Vincent N. G. Lindsay、Cyril Nicolas、André B. Charette

  DOI：10.1021/ja201237j

  日期：2011.6.15

  α-PMP-ketone group were found to be effective carbene precursors for the highly stereoselective Rh(2)(S-TCPTTL)(4)-catalyzed cyclopropanation of alkenes (EWG = NO(2), CN, CO(2)Me). The resulting products were readily transformed into a variety of biologically relevant enantiopure molecules, such as cyclopropane α- and β-amino acid derivatives. Different mechanistic studies carried out led to a rationale for the

  发现带有 α-PMP-酮基的不同二受体重氮化合物是高立体选择性 Rh(2)(S-TCPTTL)(4)-催化烯烃环丙烷化的有效卡宾前体 (EWG = NO(2), CN, CO(2)Me)。所得产物很容易转化为各种生物相关的对映体纯分子，例如环丙烷α-和β-氨基酸衍生物。进行的不同机理研究为获得的高非对映选择性和对映选择性提供了依据，其中发现 PMP-酮部分在立体诱导过程中起着关键作用。此外，还记录了使用催化量的非手性路易斯碱来影响所开发反应的对映诱导。
• Boronate Urea Activation of Nitrocyclopropane Carboxylates
  作者：Sonia S. So、Tyler J. Auvil、Victoria J. Garza、Anita E. Mattson

  DOI：10.1021/ol202873d

  日期：2012.1.20

  Boronate ureas operate as catalysts for the activation of nitrocyclopropane carboxylates in nucleophilic ring-opening reactions. A variety of amines were found to open the urea-activated nitrocyclopropane carboxylates, generating highly useful nitro ester building blocks In good yields. Standard manipulations allow access to a wide range of valuable compounds from the ring-opened products with direct applications in bioactive target synthesis.
• A Mild Procedure for the Lewis Acid-Catalyzed Ring-Opening of Activated Cyclopropanes with Amine Nucleophiles
  作者：Olga Lifchits、André B. Charette

  DOI：10.1021/ol8009286

  日期：2008.7.3

  The Lewis acid-catalyzed ring-opening of methyl 1-nitrocyclopropanecarboxylates with amine nucleophiles is described. The reaction proceeds at room temperature and with complete preservation of the enantiomeric purity from the electrophilic center of the cyclopropane to the acyclic product. The methodology was applied in an enantioselective synthesis of the dual serotonin/norepinephrine reuptake inhibitor (3R)-3-(1H-indol-1-yl)-N-methyl-3-phenylpropan-1-amine.