(S)-N-(tert-butyloxycarbonyl)-α-ethylbenzylamine | 176211-91-9

• 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: (S)-N-(tert-butyloxycarbonyl)-α-ethylbenzylamine
• 英文别名: (1-phenyl-propyl)-carbamic acid tert-butyl ester；(S)-tert-butyl 1-phenylpropylcarbamate；tert-butyl (S)-1-phenylpropylcarbamate；tert-butyl N-[(1S)-1-phenylpropyl]carbamate
• CAS: 176211-91-9
• 化学式: C₁₄H₂₁NO₂
• 分子量: 235.326
• InChiKey: ZOMRHAXWDHLHLB-LBPRGKRZSA-N

物化性质

• 熔点：
  68 °C(Solv: ethyl ether (60-29-7))
• 沸点：
  340.4±21.0 °C(Predicted)
• 密度：
  1.003±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：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  硼酸三甲酯 、 (S)-N-(tert-butyloxycarbonyl)-α-ethylbenzylamine 在 叔丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 4.5h， 生成
  参考文献：
  名称：

  New C5-Alkylated Indolobenzazepinones Acting as Inhibitors of Tubulin Polymerization: Cytotoxic and Antitumor Activities

  摘要：

  A series of 5-alkylindolobenzazepin-7-ones was synthesized by Suzuki coupling between 3-iodoindole-2-carboxylates and the appropriate alpha-alkylbenzylamino o-boronic acids followed by cyclization to the lactam. Derivatives having a linear alkyl chain at C5 were found to be highly cytotoxic to KB cells with IC50 values in the 30-80 nM range. These compounds also inhibited the polymerization of tubulin with IC50's of 1-2 mu M. Compound 4f ((S)-5-ethyl) showed comparable antiproliferative activities (IC50's of 30-70 nM) in a variety of cancer cell lines, cell growth being arrested at the G2/M phase. Compound 4f induced apoptosis in a dose-dependent manner in three different cancer cell lines and was shown to affect cell morphology in a manner consistent with its inhibitory action on tubulin polymerization. Using the experimental model of glioma grafted on the chick chorio-allantoic membrane, local treatment with compound 4f markedly reduced tumor progression.

  DOI：

  10.1021/jm701466p
• 作为产物：
  描述：

  N-Boc-(p-methoxyphenyl)benzylamine 在 正丁基锂 、 ammonium cerium(IV) nitrate 、 鹰爪豆碱 作用下， 反应 10.0h， 生成 (S)-N-(tert-butyloxycarbonyl)-α-ethylbenzylamine
  参考文献：
  名称：

  (−)-Sparteine-Mediated α-Lithiation of N-Boc-N-(p-methoxyphenyl)benzylamine:  Enantioselective Syntheses of (S) and (R) Mono- and Disubstituted N-Boc-benzylamines

  摘要：

  DOI：

  10.1021/ja9538804

文献信息

• Novel bifunctional thiourea–ammonium salt catalysts derived from amino acids: application to highly enantio- and diastereoselective aza-Henry reaction
  作者：Hong-Yu Wang、Zhuo Chai、Gang Zhao

  DOI：10.1016/j.tet.2013.04.079

  日期：2013.6

  development of new efficient and easily accessible catalysts has been one of the focuses in asymmetric phase-transfer catalysis. In this paper, a novel class of chiral bifunctional thiourea–ammonium phase-transfer catalysts were synthesized from commercially available α-amino acids. The structural modularity of these catalysts permits facile tunings to achieve optimum results, which was demonstrated

  新型高效且易于获得的催化剂的开发一直是不对称相转移催化的重点之一。在本文中，从市场上可买到的α-氨基酸合成了一类新型的手性双官能硫脲-铵相转移催化剂。这些催化剂的结构模块性使其易于调节以获得最佳结果，这在催化氮杂-亨利反应中表现出优异的对映选择性（高达99.5％ee）和非对映选择性（高达> 25：1 dr）得到了证明。
• Catalytic Enantioselective Addition of Organometallic Reagents to <i>N</i>-Formylimines Using Monodentate Phosphoramidite Ligands
  作者：Maria Gabriella Pizzuti、Adriaan J. Minnaard、Ben L. Feringa

  DOI：10.1021/jo702140f

  日期：2008.2.1

  The asymmetric synthesis of protected amines via the copper/phosphoramidite-catalyzed addition of organozinc and organoaluminum reagents to N-acylimines, generated in situ from aromatic and aliphatic α-amidosulfones, is reported. High yields of optically active N-formyl-protected amines and enantioselectivities up to 99% were obtained. Under the reaction conditions, partial oxidation of the phosphoramidite

  据报道，通过芳族和脂肪族α-酰胺基砜原位生成的铜/次膦酸酯催化的有机锌和有机铝试剂向N-酰基嘧啶的加成反应，不对称合成了受保护的胺。获得了高产率的旋光性N-甲酰基保护的胺，对映选择性高达99％。在反应条件下，检测到亚磷酰胺配体被部分氧化为相应的磷酸酰胺。初步研究了其起源及其对催化加成反应的影响。
• Heterocyclic antiviral compounds
  申请人：Gabriel Stephen Deems

  公开号：US20090028818A1

  公开（公告）日：2009-01-29

  This invention relates to piperidine derivatives of formula I wherein R 1 , R 2 , R 3 and R 4 are as defined herein useful in the treatment of a variety of disorders, including those in which the modulation of CCR5 receptors is implicated. Disorders that may be treated or prevented by the present derivatives include HIV and genetically related retroviral infections (and the resulting acquired immune deficiency syndrome, AIDS), rheumatoid arthritis, solid organ transplant reject (graft vs. host disease), asthma and COPR.

  这项发明涉及式I的哌啶衍生物，其中R1、R2、R3和R4如本文所定义，在治疗各种疾病中有用，包括那些涉及CCR5受体调节的疾病。目前的衍生物可以治疗或预防的疾病包括HIV和遗传相关的逆转录病毒感染（以及由此导致的获得性免疫缺陷综合症，艾滋病），类风湿关节炎，固体器官移植排斥（移植物对宿主病），哮喘和慢性阻塞性肺疾病。
• Novel pyrrolidine compound and a process for preparing the same
  申请人：Moritani Yasunori

  公开号：US20070167440A1

  公开（公告）日：2007-07-19

  The present invention relates to a novel pyrrolidine compound, which has a potent antagonistic activity against central cannabinoid (CB1) receptor, having the formula [I]: wherein each of R 1 and R 2 is (A) optionally substituted aryl (or heteroaryl) group, or (B) both of the groups combine to form a group of the formula: one of R 3 and R 4 is hydrogen and another is hydrogen, hydroxyl, hydroxyalkyl, etc., or both of R 3 and R 4 combine to form oxo group, R 5 is hydrogen or alkyl, Y is single bond, oxygen atom or a group of the formula: —N(R 7 )—, R 6 is optionally substituted hydrocarbon group or optionally substituted cyclic group, R 7 is alkyl or alkyloxycarbonylalkyl, provided that R 6 is not 4-amino-5-chloro-2-methoxyphenyl group when Y is single bond and one of the R 3 and R 4 is hydrogen and another is hydroxymethyl, or a pharmaceutically acceptable salt thereof.

  本发明涉及一种新型吡咯烷化合物，其具有对中枢大麻素（CB1）受体的强烈拮抗活性，其化学式为[I]：其中，R1和R2中的每一个是（A）可选取的取代芳基（或杂环芳基）基团，或者（B）两个基团结合形成式的基团：R3和R4中的一个是氢，另一个是氢、羟基、羟基烷基等，或者R3和R4结合形成氧代基团，R5是氢或烷基，Y是单键、氧原子或式的基团：—N(R7)—，R6是可选取的取代的碳氢基团或可选取的取代的环状基团，R7是烷基或烷氧羰基烷基，但当Y为单键且R3和R4中的一个为氢，另一个为羟甲基时，R6不是4-氨基-5-氯-2-甲氧基苯基团，或其药学上可接受的盐。
• Benzothiophene derivatives
  申请人：Hubbs Jed Lee

  公开号：US20090082308A1

  公开（公告）日：2009-03-26

  The present invention relates to a novel class of benzothiophene amide derivatives. The hydroxamic acid compounds can be used to treat cancer. The benzothiophene amide compounds can also inhibit histone deacetylase and are suitable for use in selectively inducing terminal differentiation, and arresting cell growth and/or apoptosis of neoplastic cells, thereby inhibiting proliferation of such cells. Thus, the compounds of the present invention are useful in treating a patient having a tumor characterized by proliferation of neoplastic cells. The compounds of the invention may also be useful in the prevention and treatment of TRX-mediated diseases, such as autoimmune, allergic and inflammatory diseases, and in the prevention and/or treatment of diseases of the central nervous system (CNS), such as neurodegenerative diseases. The present invention further provides pharmaceutical compositions comprising the hydroxamic acid derivatives and safe dosing regimens of these pharmaceutical compositions, which are easy to follow, and which result in a therapeutically effective amount of the hydroxamic acid derivatives in vivo.

  本发明涉及一类新型的苯并噻吩酰胺衍生物。这些羟肟酸化合物可用于治疗癌症。苯并噻吩酰胺化合物还可以抑制组蛋白去乙酰化酶，并适用于选择性诱导终末分化，阻止肿瘤细胞的生长和/或凋亡，从而抑制这些细胞的增殖。因此，本发明的化合物可用于治疗具有肿瘤细胞增殖特征的患者。该发明的化合物也可用于预防和治疗TRX介导的疾病，如自身免疫性、过敏性和炎症性疾病，以及中枢神经系统（CNS）疾病的预防和/或治疗，如神经退行性疾病。本发明还提供了包含羟肟酸衍生物的药物组合物和这些药物组合物的安全剂量方案，易于遵循，并在体内产生治疗有效量的羟肟酸衍生物。