(4-苄氧基-1-溴萘-2-基)氨基甲酸叔丁酯 | 122745-37-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (4-苄氧基-1-溴萘-2-基)氨基甲酸叔丁酯
• 英文名称: 2-((tert-Butyloxycarbonyl)amino)-4-(benzyloxy)-1-bromonaphthalene
• 英文别名: N-(tert-butyloxycarbonyl)-4-(benzyloxy)-1-bromo-2-naphthylamine；tert-butyl N-(1-bromo-4-phenylmethoxynaphthalen-2-yl)carbamate
• CAS: 122745-37-3
• 化学式: C₂₂H₂₂BrNO₃
• 分子量: 428.326
• InChiKey: NSRJBVJIIANTEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  111 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  502.6±45.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (4-苄氧基-1-溴萘-2-基)氨基甲酸叔丁酯 在 4-二甲氨基吡啶 lithium hydroxide 、 sodium hydroxide 、 偶氮二异丁腈 、 dimethyl sulfide borane 、 双氧水 、 三正丁基氢锡 、 sodium hydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 10.83h， 生成 (-)-(1R)-5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(hydroxymethyl)-1,2-dihydro-3H-benzindole
  参考文献：
  名称：

  Synthesis of N-(tert-butyloxycarbonyl)-CBI, CBI, CBI-CDPI1, and CBI-CDPI2: enhanced functional analogs of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI) left-hand subunit

  摘要：

  DOI：

  10.1021/jo00310a013
• 作为产物：
  描述：

  1,3-二硝基萘 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 (4-苄氧基-1-溴萘-2-基)氨基甲酸叔丁酯
  参考文献：
  名称：

  Total synthesis and evaluation of (.+-.)-N-(tert-butoxycarbonyl)-CBI, (.+-.)-CBI-CDPI1, and (.+-.)-CBI-CDPI2: CC-1065 functional agents incorporating the equivalent 1,2,9,9a-tetrahydrocyclopropa[1,2-c]benz[1,2-e]indol-4-one (CBI) left-hand subunit

  摘要：

  DOI：

  10.1021/ja00198a089

文献信息

• Synthesis and Characterization of a Cyclobutane Duocarmycin Derivative Incorporating the 1,2,10,11-Tetrahydro-9<i>H</i>-cyclobuta[<i>c</i>]benzo[<i>e</i>]indol-4-one (CbBI) Alkylation Subunit
  作者：James P. Lajiness、Dale L. Boger

  DOI：10.1021/ja106986f

  日期：2010.10.6

  spirocyclization of a phenol onto a tethered alkyl halide to form the desired cyclobutane. The conditions required for the implementation of the Ar-4' spirocyclization indicate that the entropy of activation substantially impacts the rate of reaction relative to that for the much more facile Ar-3' spirocyclization, while the higher enthalpy of activation slows the reaction relative to an Ar-5' spirocyclization

  1,2,10,11-四氢-9H-环丁[c]苯并[e]吲哚-4-酮 (17, CbBI) 的合成，其中包含 CC-1065 和多卡霉素的深层基本结构修饰详细介绍了由扩环稠合环丁烷（相对于环丙烷）掺入组成的烷基化亚基、其化学和结构表征以及其掺入天然产物的关键类似物中。CbBI 的制备方法基于先例（Ar-3' 和 Ar-5'），但之前未知的 Ar-4' 将苯酚螺环化到束缚的烷基卤上以形成所需的环丁烷。实施 Ar-4' 螺环化所需的条件表明，相对于更容易的 Ar-3' 螺环化，活化熵显着影响反应速率，而较高的活化焓相对于 Ar-3' 螺环化减慢了反应速度。 Ar-5'螺环化。基于 CbBI 的试剂的表征揭示了它们卓越的稳定性和精致的反应区域选择性，N-Boc-CbBI (13) 的单晶 X 射线结构分析揭示了它们的结构起源。反应区域选择性可能归因于两个可用的环丁烷键与环己二烯酮π-体系的立体电子排
• Atropisomerism of Aromatic Carbamates
  作者：Lutz F. Tietze、Heiko J. Schuster、J. Marian von Hof、Sonja M. Hampel、Juan F. Colunga、Michael John

  DOI：10.1002/chem.201001047

  日期：2010.11.8

  ortho‐Haloarylcarbamates like 1–4 show a high rotational barrier about the Naryl bond of up to 91.6 kJ mol−1 as found for 1, which was determined by 2D exchange NMR spectroscopy (EXSY). It was further demonstrated that the height of the barrier not only depends on the substituents at the axis of chirality, but is also influenced by electronic effects.

  邻Haloarylcarbamates像1 - 4显示关于所述N个高旋转阻挡向上的芳基键到91.6千焦摩尔-1作为找到的1，其通过二维交换NMR光谱（EXSY）测定。进一步证明，势垒的高度不仅取决于手性轴上的取代基，而且还受电子效应的影响。
• Unsymmetrical DNA Cross-Linking Agents:  Combination of the CBI and PBD Pharmacophores
  作者：Moana Tercel、Stephen M. Stribbling、Hilary Sheppard、Bronwyn G. Siim、Kent Wu、Susan M. Pullen、K. Jane Botting、William R. Wilson、William A. Denny

  DOI：10.1021/jm020526p

  日期：2003.5.1

  A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo[2,1-c][1,4]benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.
• Boger, Dale L.; Mesini, Philippe, Journal of the American Chemical Society, 1994, vol. 116, # 25, p. 11335 - 11348
  作者：Boger, Dale L.、Mesini, Philippe

  DOI：——

  日期：——
• An improved synthesis of 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (CBI): a simplified analog of the CC-1065 alkylation subunit
  作者：Dale L. Boger、Weiya Yun、Bradley R. Teegarden

  DOI：10.1021/jo00036a023

  日期：1992.5

  A concise and improved synthesis of 11, the immediate precursor to N-BOC-CBI and related analogues of CC-1065 incorporating the 1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one alkylation subunit, is detailed based on a direct 5-exo-trig aryl radical-alkene cyclization for 3-hydroxymethylindoline generation.