N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-nitrobenzylamine | 774225-21-7

• 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-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-nitrobenzylamine
• 英文别名: N-tert-butyl N-(4-nitrophenyl(phenylsulfonyl)methyl)carbamate；tert-butyl ((4-nitrophenyl)(phenylsulfonyl)methyl)carbamate；tert-butyl N-[benzenesulfonyl-(4-nitrophenyl)methyl]carbamate
• CAS: 774225-21-7
• 化学式: C₁₈H₂₀N₂O₆S
• 分子量: 392.433
• InChiKey: SSVPKGYYBAVMPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  172-174 °C
• 沸点：
  611.9±55.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-nitrobenzylamine 在 水 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 tert-butyl (S)-(2-nitro-1-(4-nitrophenyl)ethyl)carbamate
  参考文献：
  名称：

  Chiral ureas and thioureas supported on polystyrene for enantioselective aza-Henry reactions under solvent-free conditions

  摘要：

  手性可回收支持的双功能脲或硫脲在无溶剂条件下促进高对映选择性的无溶剂条件下的氮杂-Henry反应。

  DOI：

  10.1039/c4gc02474e
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 ammonium hydroxide 作用下， 以 甲醇 、 甲酸 、 乙醇 、 水 为溶剂， 反应 90.58h， 生成 N-(tert-butoxycarbonyl)-α-(phenylsulfonyl)-4-nitrobenzylamine
  参考文献：
  名称：

  Diastereo- and Enantioselective Pd(II)-Catalyzed Additions of 2-Alkylazaarenes to N-Boc Imines and Nitroalkenes

  摘要：

  A chiral Pd(II)-bis(oxazoline) complex was found to be highly effective in promoting the first direct diastereo- and enantioselective addition of alkylazaarenes to N-Boc aldimines and nitroalkenes under mild conditions. Deprotection of Boc-protected products proceeded readily to provide amines in high yields.

  DOI：

  10.1021/ja3083494

文献信息

• Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals
  作者：Patricia Gizecki、Ramzi Ait Youcef、Céline Poulard、Robert Dhal、Gilles Dujardin

  DOI：10.1016/j.tetlet.2004.10.154

  日期：2004.12

  Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective and asymmetrical way to these new heterocyclic compounds is described, together with the first evidence of their ability to undergo N-acylation.

  在路易斯酸条件下，由于损失，N -Boc，O -Me乙缩醛与（R）-（+）- O-乙烯基-泛内酯的反应不会产生预期的二氢恶嗪，但会导致相应的四氢恶嗪酮所述的吨-Bu基。描述了对这些新的杂环化合物的非对映选择性和不对称方式，以及它们经历N酰化能力的第一个证据。
• Enantioselective Addition of Thiols to Imines Catalyzed by Thiourea–Quaternary Ammonium Salts
  作者：Hong-Yu Wang、Jia-Xing Zhang、Dong-Dong Cao、Gang Zhao

  DOI：10.1021/cs400594e

  日期：2013.10.4

  Asymmetric phase-transfer catalysis was first applied to the synthesis of chiral N,S-acetals by using amino acid-based bifunctional thiourea-ammonium salt catalysts. The reaction could be performed on the gram scale to give up to 93% ee and 99% yield with a catalyst loading as low as 0.1 mol % within 5 min.

  首先使用基于氨基酸的双功能硫脲-铵盐催化剂，将不对称相转移催化应用于手性N，S-缩醛的合成。该反应可以以克为单位进行，以产生高达93％的ee和99％的产率，并且在5分钟内催化剂负载量低至0.1mol％。
• Catalytic Asymmetric Synthesis of Trisubstituted Aziridines
  作者：Li Huang、William D. Wulff

  DOI：10.1021/ja203754p

  日期：2011.6.15

  is described which provides for the direct asymmetric catalytic synthesis of trisubstituted aziridines from imines and diazo compounds. While unactivated imines were not reactive to α-diazo carbonyl compounds in which the diazo carbon was disubstituted, N-Boc imines react with both α-diazo esters and α-diazo-N-acyloxazolidinones to give trisubstituted aziridines with excellent diastereo- and enantioselectivities

  描述了一种由亚胺和重氮化合物直接不对称催化合成三取代氮丙啶的方法。虽然未活化的亚胺对重氮碳被二取代的 α-重氮羰基化合物没有反应性，但 N-Boc 亚胺与 α-重氮酯和 α-重氮-N-酰基恶唑烷酮反应生成具有优异非对映选择性和对映选择性的三取代氮丙啶。
• Asymmetric Aza-Morita-Baylis-Hillman-Type Reactions: The Highly Enantioselective Reaction between Unmodified α,β- Unsaturated Aldehydes and N-Acylimines by Organo-co-catalysis
  作者：Sylva Číhalová、Pawel Dziedzic、Armando Córdova、Jan Veselý

  DOI：10.1002/adsc.201000951

  日期：2011.5.9

  (MBH)‐type reaction between N‐carbamate‐protected imines and α,β‐unsaturated aldehydes has been developed. The organic co‐catalytic system of proline and 1,4‐diazabicyclo[2.2.2]octane (DABCO) enables the asymmetric synthesis of the corresponding N‐Boc‐ and N‐Cbz‐protected β‐amino‐α‐alkylidene‐aldehydes in good to high yields and up to 99% ee. In the case of aza‐MBH‐type addition of enals to phenylprop‐2‐ene‐1‐imines

  高对映选择性的有机助催化氮杂森田-的Baylis-希尔曼（MBH）型之间的反应ñ -氨基甲酸酯保护的亚胺和α，β不饱和醛已经研制成功。脯氨酸和1,4-二氮杂双环[2.2.2]辛烷（DABCO）的有机共催化体系可实现不对称合成相应的N - Boc-和N -Cbz保护的β-氨基-α-亚烷基-醛良品率高，ee高达99％。在苯丙-2-烯-1-亚胺的氮杂-MBH型加成反应中，助催化反应具有出色的1,2-选择性。有机-共催化的氮杂-MBH型反应也可以通过将α，β-不饱和醛直接高度对映选择性地添加到稳定的氮中来进行用氨基甲酸酯保护的α-酰胺基砜可得到相应的β-氨基-α-亚烷基醛，ee最高可达99％。有机-共催化的氮杂-MBH型反应也是近对映体纯的β-氨基-α-亚烷基-氨基酸和β-氨基-α-亚烷基-内酰胺（99％ee）的快速入口。还讨论了手性胺和DABCO共催化的aza-MBH型反应的机理和立体化学。
• Highly Enantio- and Diastereoselective Mannich Reactions of Glycine Schiff Bases with <i>in situ</i> Generated <i>N</i>-Boc-imines Catalyzed by a Cinchona Alkaloid Thiourea
  作者：Haile Zhang、Salahuddin Syed、Carlos F. Barbas

  DOI：10.1021/ol902722y

  日期：2010.2.19

  Highly enantio- and diastereoselective organocatalytic Mannich reactions of glycine Schiff bases with N-Boc-protected imines are described. Imines were generated in situ from bench-stable α-amido sulfones. Catalysis mediated by a cinchona alkaloid thiourea provided optically active α,β-diamino acid derivatives with up to 99% ee and near-perfect diastereoselection.

  描述了甘氨酸席夫碱与N - Boc保护的亚胺的高度对映和非对映选择性的有机曼尼希反应。亚胺是由稳定的α-酰胺基砜原位生成的。金鸡纳生物碱硫脲介导的催化作用可提供具有高达99％ee和近乎完美的非对映选择性的旋光性α，β-二氨基酸衍生物。