tert-butyl (4-methoxybenzyl)carbamate | 120157-94-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: tert-butyl (4-methoxybenzyl)carbamate
• 英文别名: N-(tert-butoxycarbonyl)-p-methoxybenzylamine；Tert-butyl 4-methoxybenzylcarbamate；tert-butyl N-[(4-methoxyphenyl)methyl]carbamate
• CAS: 120157-94-0
• 化学式: C₁₃H₁₉NO₃
• 分子量: 237.299
• InChiKey: OVAFZCTWIMXZLF-UHFFFAOYSA-N

物化性质

• 沸点：
  361.6±25.0 °C(Predicted)
• 密度：
  1.056±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 储存条件：
  存储条件：室温、密封、干燥

反应信息

• 作为反应物：
  描述：

  tert-butyl (4-methoxybenzyl)carbamate 在 ruthenium trichloride 、 sodium periodate 、 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 68.0h， 生成 BOC-甘氨酸
  参考文献：
  名称：

  Improved synthesis of (R)-glycine-d-15N

  摘要：

  Previously, we have synthesized the title glycine to permit assignment of the prochiral alpha -protons of glycine residues in the NMR study of the protein FKBP. A key, and low yielding step in this synthesis occurs in the ruthenium tetraoxide mediated degradation of N-t-Boc-p-methoxybenzyl amine to N-t-Boc-glycine. Efforts to improve this key step by exploring different substrates and N-protecting groups were successful to render this synthesis amenable for the large scale production of (R)-glycine-d-N-15. (C) 2001 Elsevier Science Ltd. Ail rights reserved.

  DOI：

  10.1016/s0040-4020(01)00629-9
• 作为产物：
  描述：

  tert-butyl [(4-methoxyphenyl)(tosyl)methyl]carbamate 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以87%的产率得到tert-butyl (4-methoxybenzyl)carbamate
  参考文献：
  名称：

  Reductive BOC-amination of aldehydes

  摘要：

  Base-assisted elimination-reduction of alpha -amidoalkyl sulfones with sodium borohydride proceeds in tetrahydrofuran at room temperature leading to the corresponding BOC-amines in good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00895-4

文献信息

• Study of the stability of carbocations by chlorosulfonyl isocyanate reaction with ethers
  作者：Ji Duck Kim、Gyoonhee Han、Lak Shin Jeong、Hyun-Ju Park、Ok Pyo Zee、Young Hoon Jung

  DOI：10.1016/s0040-4020(02)00413-1

  日期：2002.5

  benzyl carbocations was investigated using the novel technique for comparing the stability of carbocations in solution developed by using a simple CSI reaction with various ethers. The p-methoxycinnamyl carbocation was the most stable in our reaction system and the next stable carbocation was the p-methoxybenzyl carbocation. The stability of the other carbocations decreased with methacryl, t-butyl, cinnamyl

  使用新颖的技术研究了各种烷基，烯丙基和苄基碳阳离子的稳定性顺序，用于比较通过使用简单的CSI反应与各种醚开发的溶液中碳阳离子的稳定性。该p -methoxycinnamyl碳正离子是我们的反应体系中最稳定，下一个稳定的碳正离子是p甲氧基苄基碳正离子。其他碳正离子的稳定性按甲基丙烯酸，叔丁基，肉桂基，丙烯酸，苄基，2°和烯丙基碳正离子的顺序降低。
• The direct reductive amination of electron-deficient amines with aldehydes: the unique reactivity of the Re2O7 catalyst
  作者：Braja Gopal Das、Prasanta Ghorai

  DOI：10.1039/c2cc33185c

  日期：——

  An unprecedented direct reductive amination of electron-deficient amines such as Cbz-, Boc-, EtOCO-, Fmoc-, Bz-, ArSO2-, Ar2PO-, etc. protected amines with aldehydes is achieved using the Re2O7 catalyst and silanes as the hydride source. Excellent regioselective mono-alkylation and chemoselective reductive-amination were observed.

  首次实现了采用Re2O7催化剂和硅烷作为氢源，对Cbz-、Boc-、EtOCO-、Fmoc-、Bz-、ArSO2-、Ar2PO-等电子不足的胺类保护基胺与醛的直接还原胺化反应。观察到优异的区域选择性单烃基化和化学选择性还原胺化。
• Studies on the Transformation of Azido-Group to N-(t-Butoxycarbonyl)amino Group<i>via</i>Staudinger Reaction
  作者：Carlos A. M. Afonso

  DOI：10.1080/00397919808005719

  日期：1998.1

  tri-n-butylphosphine, followed by addition of di-t-butyl dicarbonate (Boc2O) affords, N-(t-Butoxycarbonyl)amines 2 in moderate to good overall yields. For secondary azides the formation of symmetrical disubstituted ureas is a competitive process. Conditions were found which, in the presence of a primary amine, allow for moderate selectivity for the reaction with Boc2O.

  摘要 通过简单直接的顺序，用三正丁基膦处理伯叠氮化物，然后加入二碳酸二叔丁酯 (Boc2O)，以中等至良好的总产率提供 N-（叔丁氧基羰基）胺 2。对于仲叠氮化物，对称双取代脲的形成是一个竞争过程。发现在伯胺的存在下允许与Boc 2 O反应具有中等选择性的条件。
• Versatile solid-phase synthesis of secondary amines from alcohols. Development of an N-Boc-(o-nitrobenzene)sulfonamide linker
  作者：Miles S. Congreve、Corinne Kay、Jan J. Scicinski、Steven V. Ley、Geoffrey Williams、Peter J. Murray、Stephen C. McKeown、Stephen P. Watson

  DOI：10.1016/s0040-4039(03)00574-4

  日期：2003.5

  releasing linker based on the modified o-nitrobenzene sulfonamide protective group is described. This new N-Boc-o-nitrobenzenesulfonamide (Boc-ONBS) linker enables the elaboration on resin of primary and secondary amines by sequential substitution of the sulfonamide moiety using the Mitsunobu reaction. A 16-member array of secondary and Boc protected primary amines was then prepared using this linker.

  描述了基于改性的邻硝基苯磺酰胺保护基的通用的胺释放接头的开发。这种新的N -Boc- o-硝基苯磺酰胺（Boc-ONBS）接头可通过使用Mitsunobu反应依次取代磺酰胺部分，从而在伯胺和仲胺树脂上进行精制。然后使用该接头制备了由16个成员组成的仲和Boc保护的伯胺阵列。
• Preparation of Enantiopure Chiral Amino-[D₁]methyllithium Compounds and Determination of Their Micro- and Macroscopic Configurational Stabilities
  作者：Dagmar C. Kapeller、Friedrich Hammerschmidt

  DOI：10.1002/chem.200802668

  日期：2009.6.2

  Enantiopure aminomethyllithiums, such as depicted, the smallest of their kind, have been prepared and tested for their micro‐ and macroscopic configurational stabilities, which are delicately influenced by R1 and R2. The species with R1=R2=Bn is macroscopically configurationally stable below −95 °C.

  越小越好：对映纯氨基甲基锂，如图所示，是同类中最小的，已经制备并测试了它们的微观和宏观构型稳定性，这些稳定性受到 R 1和 R 2 的微妙影响。R 1 =R 2 =Bn 的物质在-95 °C 以下宏观构型稳定。