[(S)-2-(2-bromophenyl)-1-methylethyl]carbamic acid tert-butyl ester

• 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)-2-(2-bromophenyl)-1-methylethyl]carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-(2-bromophenyl)propan-2-yl]carbamate
• 化学式: C₁₄H₂₀BrNO₂
• 分子量: 314.222
• InChiKey: ZWNWQPKGRCKBDC-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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)-2-(2-bromophenyl)-1-methylethyl]carbamic acid tert-butyl ester 在 tris(dibenzylideneacetone)dipalladium (0) 、 三(邻甲基苯基)磷 caesium carbonate 作用下， 以 甲苯 为溶剂， 反应 15.0h， 以63%的产率得到N-Boc-(S)-2-methylindoline
  参考文献：
  名称：

  Synthesis of 2-substituted indolines using sequential Pd-catalyzed processesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all products without elemental analysis data (3c–g and 4d–g). See http://www.rsc.org/suppdata/p1/b2/b200163b/

  摘要：

  通过钯催化氨基官能化有机锌试剂与 2-溴碘苯偶联，然后进行布赫瓦尔德钯催化分子内胺化反应，开发出了一条制备对映体纯度为 2-取代吲哚类化合物 4a-g 和 2-取代四氢喹啉 4h 的简便路线。初始偶联的收率不高（36-52%），但环化收率令人满意（63-87%）。通过手性相高效液相色谱法确定了一个代表性实例的立体化学完整性。

  DOI：

  10.1039/b200163b
• 作为产物：
  描述：

  N-Boc-L-丙氨醇 在 咪唑 、 sodium periodate 、 lithium chloro-isopropyl-magnesium chloride 、 氯化亚砜 、 ruthenium(IV) oxide hydrate 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 9.0h， 生成 [(S)-2-(2-bromophenyl)-1-methylethyl]carbamic acid tert-butyl ester
  参考文献：
  名称：

  Ring opening of cyclic sulfamidates with bromophenyl metal reagents: complementarity of sulfamidates and aziridines

  摘要：

  Bromophenyl magnesium reagents generated via a Knochel type magnesium halogen exchange of aryl iodides undergo regioselective ring opening of cyclic primary and secondary N-Boc sulfamidates in good to excellent yields. With secondary sulfamidates the reaction proceeds with clean inversion of the stereochemistry. This protocol complements the ring opening of aziridines with bromophenyl metal reagents and extends its scope to secondary substrates. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.07.123

文献信息

• Synthesis of 2-substituted indolines using sequential Pd-catalyzed processesElectronic supplementary information (ESI) available: 1H and 13C NMR spectra for all products without elemental analysis data (3c–g and 4d–g). See http://www.rsc.org/suppdata/p1/b2/b200163b/
  作者：Hervé J. C. Deboves、Christopher Hunter、Richard F. W. Jackson

  DOI：10.1039/b200163b

  日期：2002.3.8

  A concise route to enantiomerically pure 2-substituted indolines 4a–g and a 2-substituted tetrahydroquinoline 4h has been developed by application of the Pd-catalyzed coupling of amino functionalised organozinc reagents with 2-bromoiodobenzene, followed by Buchwald's palladium-catalyzed intramolecular amination reaction. The yields in the initial coupling are modest (36–52%), but the cyclisation yields are satisfactory (63–87%). The stereochemical integrity of a representative example was established by chiral phase HPLC.

  通过钯催化氨基官能化有机锌试剂与 2-溴碘苯偶联，然后进行布赫瓦尔德钯催化分子内胺化反应，开发出了一条制备对映体纯度为 2-取代吲哚类化合物 4a-g 和 2-取代四氢喹啉 4h 的简便路线。初始偶联的收率不高（36-52%），但环化收率令人满意（63-87%）。通过手性相高效液相色谱法确定了一个代表性实例的立体化学完整性。
• Ring opening of cyclic sulfamidates with bromophenyl metal reagents: complementarity of sulfamidates and aziridines
  作者：Paul Hebeisen、Urs Weiss、André Alker、Andreas Staempfli

  DOI：10.1016/j.tetlet.2011.07.123

  日期：2011.10

  Bromophenyl magnesium reagents generated via a Knochel type magnesium halogen exchange of aryl iodides undergo regioselective ring opening of cyclic primary and secondary N-Boc sulfamidates in good to excellent yields. With secondary sulfamidates the reaction proceeds with clean inversion of the stereochemistry. This protocol complements the ring opening of aziridines with bromophenyl metal reagents and extends its scope to secondary substrates. (C) 2011 Elsevier Ltd. All rights reserved.