N-[(3-methyl-2-butenyl)oxycarbonyl]-2-phenylethylamine | 648910-19-4

• 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: N-[(3-methyl-2-butenyl)oxycarbonyl]-2-phenylethylamine
• 英文别名: prenyl N-(2-phenylethyl)carbamate；3-Methylbut-2-en-1-yl (2-phenylethyl)carbamate；3-methylbut-2-enyl N-(2-phenylethyl)carbamate
• CAS: 648910-19-4
• 化学式: C₁₄H₁₉NO₂
• 分子量: 233.31
• InChiKey: SZPYZESVHVXONR-UHFFFAOYSA-N

物化性质

• 沸点：
  364.4±31.0 °C(Predicted)
• 密度：
  1.027±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  N-[(3-methyl-2-butenyl)oxycarbonyl]-2-phenylethylamine 在 (μ₃,η²,η³,η⁵-acenaphthylene)Ru₃(CO)₇ 、 二甲基苯基硅烷 作用下， 以 乙二醇二甲醚 为溶剂， 反应 7.0h， 以65%的产率得到2-苯乙胺
  参考文献：
  名称：

  氢硅烷并不总是羰基化合物的还原剂，II：氨基甲酸酯、碳酸酯、酯和醚中叔丁基的钌催化脱保护

  摘要：

  氢硅烷作为一种试剂，通过三钌簇的催化裂解氨基甲酸酯、碳酸酯、酯和醚中 OtBu 基团的 C-O 键。该反应提供了一种在中性条件下对 OtBu 基团进行脱保护的新方法，显示出使用传统布朗斯台德或路易斯酸性促进剂从未实现过的独特选择性。在 NMR 光谱分析的基础上讨论了 C-O 裂解的可能机制。

  DOI：

  10.1002/ejoc.200901279
• 作为产物：
  描述：

  (2-iodo-3-methoxy-3-methylbutyl) N-(2-phenylethyl)carbamate 在 4-二甲氨基吡啶 、 碘 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 N-[(3-methyl-2-butenyl)oxycarbonyl]-2-phenylethylamine
  参考文献：
  名称：

  Prenyl carbamates: preparation and deprotection

  摘要：

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.03.028

文献信息

• One-pot selective cleavage of prenyl carbamates using iodine in methanol followed by zinc
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tetlet.2003.10.058

  日期：2003.12

  The prenyloxycarbonyl (Preoc) moiety was efficiently removed from carbamates to provide the corresponding amines in good to excellent yields (63-88%) by using iodine in methanol followed by treatment of the resulting beta-methoxyiodides by zinc powder. The reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic methyl ethers. (C) 2003 Elsevier Ltd. All rights reserved.
• Prenyl carbamates: preparation and deprotection
  作者：Jean-Michel Vatèle

  DOI：10.1016/j.tet.2004.03.028

  日期：2004.5

  Prenyloxycarbonylimidazole (PreocIm) and prenyl p-nitrophenyl carbonate (PreocOC(6)H(4)p-NO2), two substitutes for the unstable prenyl chloroformate, allowed an efficient introduction of the prenyloxycarbonyl group to a variety of primary and secondary amines. Deprotection of prenyl carbamates was readily achieved by, first their conversion to 2-iodo-3-methoxy-3-methylbutyl carbamates with iodine in methanol followed by reductive beta-elimination with zinc powder. These reaction conditions are compatible with the presence of a number of functional groups such as Boc and Cbz carbamates, sulfides, double bonds, indoles and aromatic ethers. (C) 2004 Elsevier Ltd. All rights reserved.
• Hydrosilanes Are Not Always Reducing Agents for Carbonyl Compounds, II: Ruthenium-Catalyzed Deprotection of tert-Butyl Groups in Carbamates, Carbonates, Esters, and Ethers
  作者：Shiori Hanada、Akihiro Yuasa、Hirotaka Kuroiwa、Yukihiro Motoyama、Hideo Nagashima

  DOI：10.1002/ejoc.200901279

  日期：2010.2

  Hydrosilanes act as a reagent to cleave the C–O bond of OtBu groups in carbamates, carbonates, esters, and ethers by catalysis of a triruthenium cluster. The reaction offers a novel deprotection method for OtBu groups under neutral conditions, showing unique selectivities that have never been accomplished with conventional Bronsted or Lewis acidic promoters. Possible mechanisms for C–O cleavage are

  氢硅烷作为一种试剂，通过三钌簇的催化裂解氨基甲酸酯、碳酸酯、酯和醚中 OtBu 基团的 C-O 键。该反应提供了一种在中性条件下对 OtBu 基团进行脱保护的新方法，显示出使用传统布朗斯台德或路易斯酸性促进剂从未实现过的独特选择性。在 NMR 光谱分析的基础上讨论了 C-O 裂解的可能机制。