methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate | 19901-50-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate
• 英文别名: N-tert-butoxycarbonyl-phenylalanine methyl ester；methyl 2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoate
• CAS: 19901-50-9
• 化学式: C₁₅H₂₁NO₄
• 分子量: 279.336
• InChiKey: SDSWSVBXRBXPRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate 在 lithium aluminium tetrahydride 作用下， 生成 N-Boc-DL-苯丙氨醇
  参考文献：
  名称：

  Structure–activity relationships of diamine inhibitors of cytochrome P450 (CYP) 3A as novel pharmacoenhancers, part I: Core region

  摘要：

  Ritonavir (RTV), an HIV-1 protease inhibitor (PI), is also a potent mechanism-based inhibitor of human cytochrome P450 3A (CYP3A) and has been widely prescribed as a pharmacoenhancer. As a boosting agent for marketed PIs, it reduces pill burden, and improves compliance. Removal of the hydroxyl group from RTV reduces, but does not eliminate HIV PI activity and does not affect CYP3A inhibition. Herein we report the discovery of a novel series of CYP3A inhibitors that are devoid of antiviral activity. The synthesis and evaluation of analogs with extensive modifications of the 1,4-diamine core along with the structure activity relationships with respect to anti-HIV activity, CYP3A inhibitory activity, selectivity against other CYP enzymes and the human pregnane X receptor (PXR) will be discussed. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.058
• 作为产物：
  描述：

  N-[(tert-butoxy)carbonyl]-L-cysteine methyl ester 在 1,4-二碘代丁烷 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 氯化铵 、 锌 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 methyl 2-tert-butoxycarbonylamino-3-phenylpropanoate
  参考文献：
  名称：

  Cu（OTf）2促进烷基溴化物向脱氢丙氨酸的添加1,4-

  摘要：

  开发了Zn / Cu（OTf）2介导的烷基溴在水性介质下以高至高收率向包括二肽和三肽的脱氢丙氨酸（Dha）衍生物中添加烷基溴的方法。该协议允许从Dha衍生物选择性和生物相容地访问各种氨基酸单元。

  DOI：

  10.1021/acs.joc.9b00369

文献信息

• [EN] COMPOUNDS AS MODULATORS OF TIGIT SIGNALLING PATHWAY<br/>[FR] COMPOSÉS MODULATEURS DE LA VOIE DE SIGNALISATION DE TIGIT
  申请人：AURIGENE DISCOVERY TECH LTD

  公开号：WO2018047139A1

  公开（公告）日：2018-03-15

  The present invention relates to compound of formula (I) as therapeutic agents to modulate the TIGIT signalling pathway. The invention also encompasses the use of the compound of formula (I) or a stereoisomer thereof or a pharmaceutically acceptable salt thereof for the treatment of diseases or disorders mediated by TIGIT.

  本发明涉及一种化合物，其化学式为（I），作为调节TIGIT信号通路的治疗剂。该发明还涵盖了利用化合物（I）或其立体异构体或其药学上可接受的盐来治疗由TIGIT介导的疾病或紊乱。
• Heterocyclic amide compounds and pharmaceutical use of the same
  申请人：The Green Cross Corporation

  公开号：US05948785A1

  公开（公告）日：1999-09-07

  Heterocyclic amide compounds of the formula (I) ##STR1## wherein each symbol is as defined in the specification, pharmacologically acceptable salts thereof, pharmaceutical compositions thereof and pharmaceutical use thereof. The heterocyclic amide compounds and pharmacologically acceptable salts thereof of the present invention have superior inhibitory activity against chymase groups in mammals inclusive of human, and can be administered orally or parenterally. Therefore, they are useful as chymase inhibitors and can be effective for the prophylaxis and treatment of various diseases caused by chymase, such as those caused by angiotensin II.

  式(I)的杂环酰胺化合物##STR1##，其中每个符号如规范中定义的那样，其药理学上可接受的盐，其药物组合物和其药用。本发明的杂环酰胺化合物及其药理学上可接受的盐对哺乳动物包括人类的胰蛋白酶组具有优越的抑制活性，并可经口或经肠外途径给药。因此，它们可用作胰蛋白酶抑制剂，并可有效预防和治疗由胰蛋白酶引起的各种疾病，如由II型血管紧张素引起的疾病。
• Processes for producing .alpha.-halo ketones, .alpha.-halohydrins and
  申请人：Kaneka Corporation

  公开号：US05929284A1

  公开（公告）日：1999-07-27

  Processes for efficiently producing .alpha.-halo ketones, .alpha.-halohydrins and epoxides on an industrial scale. The prosesses include one for producing an .alpha.-halo ketone of general formula (3) by decarboxylating a product of reaction between a carboxilic acid derivative of general formula (1) and a metal enolate prepared from an .alpha.-haloacetic acid of general formula (2) or an acceptable salt thereof, one for producing an by reducing the .alpha.-halo ketone (3), and one for producing an epoxide (13) by treating the .alpha.-halohydrin (11) with a base to effect ring closure. The above prosesses are particularly suitable for producing optically active .alpha.-halo ketones, .alpha.-halohydrins and epoxides from the corresponding .alpha.-amino acid derivatives. ##STR1##

  工业规模上高效生产α-卤代酮、α-卤代醇和环氧化合物的方法。这些方法包括通过脱羧一种由一般公式(1)的羧酸衍生物与由一般公式(2)的α-卤代乙酸或其可接受的盐制得的金属烯醇盐的反应产物来生产一般公式(3)的α-卤代酮的一种方法，通过还原α-卤代酮(3)来生产α-卤代醇的一种方法，以及通过用碱处理α-卤代醇(11)以实现环闭合来生产环氧化合物(13)的一种方法。上述过程特别适用于从相应的α-氨基酸衍生物生产光学活性的α-卤代酮、α-卤代醇和环氧化合物。
• Catalytic Methyl Transfer from Dimethylcarbonate to Carboxylic Acids
  作者：Yuan Ji、Jessica Sweeney、Jillian Zoglio、David J. Gorin

  DOI：10.1021/jo401941v

  日期：2013.11.15

  Although methylation reactions are commonplace, currently used reagents are hazardous, toxic, and/or unstable. Dimethylcarbonate has been put forth as an inexpensive, nontoxic, and “green” potential methylating reagent. Herein we report a general, base-catalyzed methyl transfer from dimethylcarbonate to carboxylic acids. High selectivity for esterification is observed even in the presence of unprotected

  尽管甲基化反应很普遍，但是当前使用的试剂是危险的，有毒的和/或不稳定的。碳酸二甲酯已被提出为廉价，无毒且“绿色”的潜在甲基化试剂。本文中，我们报道了一般的碱催化的甲基碳酸酯从碳酸二甲酯向羧酸的转移。即使在未保护的苯酚存在下，也观察到了对酯化的高选择性，温和的反应条件使在可差向立体中心处的立体化学得以保留。同位素标记研究表明，机制是通过将甲基直接从碳酸二甲酯转移到底物上来进行的。
• Useful Reagents for Introduction of Boc and Fmoc Protective Groups to Amines­: Boc-DMT and Fmoc-DMT
  作者：Munetaka Kunishima、Kazuhito Hioki、Mizuho Kinugasa、Michiko Kishimoto、Miho Fujiwara、Shohei Tani

  DOI：10.1055/s-2006-942389

  日期：2006.6

  New amino-protecting reagents, Boc-DMT and Fmoc-DMT, were prepared, and found to be useful for the introduction of Boc and Fmoc groups into amines. Both the reagents can protect various amines including amino acids in good yield in aqueous media. Since the reagents are neither unstable nor irritating, they are practically useful.

  制备了新的氨基保护试剂 Boc-DMT 和 Fmoc-DMT，发现它们可用于将 Boc 和 Fmoc 基团引入胺中。这两种试剂都可以在水性介质中以良好的收率保护各种胺，包括氨基酸。由于这些试剂既不稳定也没有刺激性，因此非常实用。

表征谱图