benzyl (2-allylphenyl)carbamate | 86136-89-2

• 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: benzyl (2-allylphenyl)carbamate
• 英文别名: N-Cbz-o-allylaniline；N-Cbzo o-allylaniline；N-benzyloxycarbonyl-o-allylaniline；N-benzyloxycarbonyl-2-allylaniline；benzyl N-(2-prop-2-enylphenyl)carbamate
• CAS: 86136-89-2
• 化学式: C₁₇H₁₇NO₂
• 分子量: 267.327
• InChiKey: MZRPUIPGSDIGBT-UHFFFAOYSA-N

物化性质

• 熔点：
  57-60 °C
• 沸点：
  367.9±31.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 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：

  benzyl (2-allylphenyl)carbamate 在 氯[2-(二叔丁基磷)二苯基]金 、 silver trifluoromethanesulfonate 作用下， 以 1,4-二氧六环 为溶剂， 反应 47.0h， 以59%的产率得到2-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  金（I）催化的烯基氨基甲酸酯的分子内加氢胺化反应。

  摘要：

  DOI：

  10.1002/anie.200600052
• 作为产物：
  描述：

  N-烯丙基苯胺 在 三氟化硼乙醚 、 四丁基溴化铵 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 benzyl (2-allylphenyl)carbamate
  参考文献：
  名称：

  Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts

  摘要：

  A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The catalytic process was shown to be highly versatile and applicable to a wide range of substrates due to the flexible catalytic mechanism utilizing a noncovalent interaction.

  DOI：

  10.1021/ol401538b

文献信息

• Improved Protocol for Asymmetric, Intramolecular Heteroatom Michael Addition Using Organocatalysis: Enantioselective Syntheses of Homoproline, Pelletierine, and Homopipecolic Acid
  作者：Erik C. Carlson、Lauren K. Rathbone、Hua Yang、Nathan D. Collett、Rich G. Carter

  DOI：10.1021/jo800749t

  日期：2008.7.1

  indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

  描述了使用有机催化的分子内杂原子迈克尔加成构建对映体富集的吡咯烷、二氢吲哚和哌啶环的改进方案。已完成对高脯氨酸、高哌可酸和匹莱林的对映选择性合成的应用。
• Copper Catalyzed Enantioselective Intramolecular Aminooxygenation of Alkenes
  作者：Peter H. Fuller、Jin-Woo Kim、Sherry R. Chemler

  DOI：10.1021/ja806585m

  日期：2008.12.31

  methyleneoxy-functionalized dihydroindolines and pyrrolidines. Tetramethylaminopyridyl radical (TEMPO) serves as both the source of the oxygen and the stoichiometric oxidant. These reactions are catalyzed by copper(II) triflate, complexed with (4S,5R)-Bis-Phbox. The unprotected aminoalcohols can be obtained by sequential dissolving metal reductions of the N-S and O-N bonds.

  本文报道了铜催化的烯烃的对映选择性分子内氨基氧化。这是对映选择性分子内烯烃氨基氧化过程的第一份报告。N-Arylsulfonyl-2-allylanilines 和 4-pentenylarylsulfonamides 以高产率和良好的对映选择性环化，提供新的手性亚甲氧基官能化二氢二氢吲哚和吡咯烷。四甲基氨基吡啶基（TEMPO）既是氧源又是化学计量氧化剂。这些反应由与 (4S,5R)-Bis-Phbox 络合的三氟甲磺酸铜 (II) 催化。未保护的氨基醇可以通过连续溶解 NS 和 ON 键的金属还原来获得。
• <i>m</i>-CPBA-Mediated IntramolecularAminohydroxylation of<i>N</i>-Sulfonyl Aminoalkenes to Synthesize β-Hydroxyl Cyclic Amines
  作者：Yan Yin、Hong Zhou、Guofeng Sun、Xichen Liu

  DOI：10.1002/jhet.2169

  日期：2015.9

  diverse N‐sulfonyl‐protected aminoalkenes readily reacted with m‐CPBA to produce a series of β‐hydroxyl cyclic amines in high yields through intramolecular aminohydroxylation. This metal‐free and easy‐to‐handle synthetic methodology offered an environmentally friendly alternative to vicinal difunctionalization of alkenes.

  各种结构多样的N磺酰基保护的氨基烯烃容易与m- CPBA反应，通过分子内氨基羟基化反应以高收率产生一系列β-羟基环胺。这种无金属且易于处理的合成方法为烯烃的邻位双官能化提供了一种环境友好的替代方法。
• Thioamination of Alkenes with Hypervalent Iodine Reagents
  作者：Pushpak Mizar、Rebecca Niebuhr、Matthew Hutchings、Umar Farooq、Thomas Wirth

  DOI：10.1002/chem.201504636

  日期：2016.1.26

  An efficient thioamination of alkenes mediated by iodine(III) reagents is described. The use of different sulfur nucleophiles allows the flexible synthesis of 1,2‐aminothiols from alkenes. By employing chiral iodine(III) reagents, a stereoselective version of the thioamination protocol has also been developed.

  描述了由碘（III）试剂介导的烯烃的有效硫胺化。使用不同的硫亲核试剂可以从烯烃灵活地合成1,2-氨基硫醇。通过使用手性碘（III）试剂，还开发了硫代胺化方案的立体选择形式。
• Iron-mediated one-pot formal nitrocyclization onto unactivated alkenes
  作者：Tsuyoshi Taniguchi、Tatsuya Fujii、Hiroyuki Ishibashi

  DOI：10.1039/c0ob00905a

  日期：——

  One-pot synthesis of heterocycles having a nitromethyl group was achieved by sequential steps that involved chloronitration of alkenes using iron(III) nitrate nonahydrate followed by elimination and intramolecular Michael addition. This reaction provides an efficient method for the synthesis of heterocycles due to the simple experimental procedure and the use of inexpensive reagents of low toxicity.

  通过顺序步骤实现了具有硝基甲基基团的杂环的一锅合成，该过程包括使用氮酸铁(III)非水合物进行烯烃的氯硝化，随后进行消除反应和分子内迈克尔加成。这一反应提供了一种高效的杂环合成方法，具有实验步骤简单、使用低毒性且价格便宜的试剂等优点。