tert-butyl (3-(o-tolyl)propyl)carbamate | 147410-35-3

• 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: tert-butyl (3-(o-tolyl)propyl)carbamate
• 英文别名: tert-butyl N-[3-(2-methylphenyl)propyl]carbamate
• CAS: 147410-35-3
• 化学式: C₁₅H₂₃NO₂
• mdl: MFCD24393274
• 分子量: 249.353
• InChiKey: CANBJWLXOLNHCM-UHFFFAOYSA-N

物化性质

• 沸点：
  370.9±21.0 °C(Predicted)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.533
• 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：

  tert-butyl (3-(o-tolyl)propyl)carbamate 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 3-o-tolylpropylamine trifluoroacetate
  参考文献：
  名称：

  A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure–activity relationships

  摘要：

  A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the G 11, 12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.041
• 作为产物：
  描述：

  2-碘代甲苯 、 叔丁氧基 N-氨基甲酸丙烯 在 bis-triphenylphosphine-palladium(II) chloride 9-硼双环[3.3.1]壬烷 、 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 tert-butyl (3-(o-tolyl)propyl)carbamate
  参考文献：
  名称：

  A new type of ketolides bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether synthesis and structure–activity relationships

  摘要：

  A new type of ketolides, bearing an N-aryl-alkyl acetamide moiety at the C-9 iminoether and a cyclic carbonate at the G 11, 12 position was prepared and the antibacterial activities of the compounds were evaluated. Some of the derivatives showed potent antibacterial activity against both Haemophilus influenzae and Streptococcus pneumoniae, which are clinically important respiratory tract pathogens. Among the derivatives prepared, compound 5s with a quinolin-4-yl moiety was found to have potent and well-balanced activity against S. pneumoniae and H. influenzae including erythromycin-resistant strains. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.07.041

文献信息

• Regioselective Rhodium(I)-Catalyzed Hydroarylation of Protected Allylic Amines with Arylboronic Acids
  作者：Gavin Chit Tsui、Frederic Menard、Mark Lautens

  DOI：10.1021/ol100974f

  日期：2010.6.4

  A novel regioselective rhodium(I)-catalyzed hydroarylation of unactivated alkenes with arylboronic acids is described. The catalytic system employs [Rh(COD)OH]2 and BINAP to effect the addition of various arylboronic acids to protected allylic amines. The regioselectivity was found to be highly dependent on the protecting group, favoring the linear addition product with up to 92% yield and >20:1 regioselectivity

  描述了一种新型的区域选择性铑（I）催化的未活化烯烃与芳基硼酸的氢芳基化反应。该催化体系使用[Rh（COD）OH] 2和BINAP来实现将各种芳基硼酸添加到受保护的烯丙基胺中。发现区域选择性高度依赖于保护基，有利于线性加成产物，具有高达92％的产率和> 20：1的区域选择性。
• Direct Alkylation of 1-Azabicyclo[1.1.0]butanes
  作者：Ryan Gianatassio、Dora Kadish

  DOI：10.1021/acs.orglett.9b00321

  日期：2019.4.5

  functionalized azetidines has been an ongoing challenge. Here, we report a general method to directly alkylate 1-azabicyclo[1.1.0]butane (ABB) with organometal reagents in the presence of Cu(OTf)2 to rapidly prepare bis-functionalized azetidines. This method allows for the preparation of azetidines bearing alkyl, allyl, vinyl, and benzyl groups. This catalyst system was extended to aziridines and spirocycles

  容易的功能化氮杂环丁烷的合成一直是一个持续的挑战。在这里，我们报告了一种在Cu（OTf）2存在下用有机金属试剂直接烷基化1-氮杂双环[1.1.0]丁烷（ABB）的一般方法，以快速制备双官能化氮杂环丁烷。该方法允许制备带有烷基，烯丙基，乙烯基和苄基的氮杂环丁烷。该催化剂体系扩展到氮丙啶和螺环。快速且高收率地制备了几种结构单元和类药物化合物。
• Effects of remote N-(tert-butoxycarbonyl) groups on heteroatom directed lithiation at benzylic positions
  作者：Robin D. Clark、Jahangir

  DOI：10.1016/s0040-4020(01)90188-7

  日期：1993.2

  Lithiation of N-BOC-2-methylphenethylamine (6) occurs exclusively at the methyl group whereas lithiation of the phenylpropyl congener (11) is less regioselective. N-BOC-phenylpropylamine (17) is efficiently lithiated at the benzylic position while N-BOC-2-methylphenylbutylamine (23) undergoes lithiation of the methyl group but with low conversion. The results are discussed from the general perspective

  N -BOC -2-甲基苯乙胺（6）的锂化仅发生在甲基上，而苯丙基同类物（11）的锂化具有较低的区域选择性。N -BOC-苯基丙胺（17）在苄基位置上被有效地锂化，而N -BOC-2-甲基苯基丁胺（23）经历甲基的锂化但转化率低。从杂原子定向金属化的一般角度讨论了结果。几种硫代衍生物可以转化为杂环，例如四氢-3-苯并ze庚因-2-酮（10），六氢-3-苯并偶氮星-2-酮（16）和3-苯基吡咯烷酮（19-22）。