methyl 2-(((benzyloxy)carbonyl)amino)butanoate | 134306-32-4

• 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-(((benzyloxy)carbonyl)amino)butanoate
• 英文别名: Methyl 2-([(benzyloxy)carbonyl]amino)butanoate；methyl 2-(phenylmethoxycarbonylamino)butanoate
• CAS: 134306-32-4
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: OOOAOOYFCAQQEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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-(((benzyloxy)carbonyl)amino)butanoate 在 palladium on activated carbon 、 氢气 、 sodium hydride 、 肼 作用下， 以 甲醇 、 乙醇 、 苯 为溶剂， 反应 58.0h， 生成 6-ethyl-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole
  参考文献：
  名称：

  2,4-Diamino-8-quinazoline carboxamides as novel, potent inhibitors of the NAD hydrolyzing enzyme CD38: Exploration of the 2-position structure-activity relationships

  摘要：

  Starting from 4-amino-8-quinoline carboxamide lead 1a and scaffold hopping to the chemically more tractable quinazoline, a systematic exploration of the 2-substituents of the quinazoline ring, utilizing structure activity relationships and conformational constraint, resulted in the identification of 39 novel CD38 inhibitors. Eight of these analogs were 10-100-fold more potent human CD38 inhibitors, including the single digit nanomolar inhibitor 1am. Several of these molecules also exhibited improved therapeutic indices relative to hERG activity. A representative analog 1r exhibited suitable pharmacokinetic parameters for in vivo animal studies, including moderate clearance and good oral bioavailability. These inhibitor compounds will aid in the exploration of the enzymatic functions of CD38, as well as furthering the study of the therapeutic implications of NAD enhancement in metabolic disease models. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2018.03.021
• 作为产物：
  描述：

  N-benzyloxycarbonyl α-chloro glycine methyl ester 生成 methyl 2-(((benzyloxy)carbonyl)amino)butanoate
  参考文献：
  名称：

  CASTELHANO, A. L.;HORNE, S.;TAYLOR, G. J.;BILLEDEAU, R.;KRANTZ, A., TETRAHEDRON, 44,(1988) N 17, C. 5451-5466

  摘要：

  DOI：

文献信息

• 一种含巯基或者二硫键的有机化合物的脱硫方法
  申请人：湖州中科颐格生物科技有限公司

  公开号：CN110128252B

  公开（公告）日：2022-04-01

  本发明涉及一种有机化合物的脱硫方法，尤其涉及一种含巯基或者二硫键的有机化合物的脱硫方法。具体如下：将含巯基或者二硫键的有机化合物溶于溶剂，加入膦试剂、引发剂后，在光照下反应，使底物转化为相应的脱硫产物。所述含巯基或者二硫键的有机化合物为R‑SH或R‑S‑S‑R；其中，R为伯碳、仲碳、叔碳基团、芳香基或酰基。本发明具有无需金属参与、反应条件温和的特点。并且该方法有产率高、底物适用范围广、溶剂适用种类多的优点，广泛适用于多种脱巯基反应，以及二硫化物的脱硫反应。
• A Mild, General, <scp>Metal‐Free</scp> Method for Desulfurization of Thiols and Disulfides Induced by <scp>Visible‐Light</scp>
  作者：Wenting Qiu、Shuai Shi、Ruining Li、Xianfeng Lin、Liangming Rao、Zhankui Sun

  DOI：10.1002/cjoc.202000607

  日期：2021.5

  A visible‐light‐induced metal‐free desulfurization method for thiols and disulfides has been explored. This radical desulfurization features mild conditions, robustness, and excellent functionality compatibility. It was successfully applied not only to the desulfurization of small molecules, but also to peptides.

  探索了一种可见光诱导的无金属硫醇和二硫化物脱硫方法。这种自由基脱硫具有温和的条件，坚固性和出色的功能兼容性。它不仅成功地用于小分子的脱硫，而且还成功地应用于肽。
• Synthesis of α-amino acids with β,γ-unsaturated side chains
  作者：Arlindo L. Castelhano、Stephen Horne、Gregg J. Taylor、Roland Billedeau、Allen Krantz

  DOI：10.1016/s0040-4020(01)86051-8

  日期：1988.1

  α-Amino acids with allenyl, vinyl, and acetylenic side chains can be synthesized using non-enolate based strategies. The ester enolate-Claisen rearrangement applied to propargylic esters of N -protected α-amino acids ie of limited utility since only poor yields of allenic product are obtained with the N-Boc glycine esters, the system which give the most reproducible results. However, α-allenyl-α-amino

  具有烯基，乙烯基和炔属侧链的α-氨基酸可以使用基于非烯醇化物的策略合成。酯烯酸酯-克莱森重排应用于N-保护的α-氨基酸的炔丙基酯，即具有有限的用途，因为使用N-Boc甘氨酸酯仅能得到较低收率的艾伦产物，该系统提供了最可重复的结果。但是，在α-碳上完全官能化的α-烯基-α-氨基酸可通过4-烯基-2-苯基恶唑酮（通过环化和克莱森重排从N-苯甲酰基保护的氨基酸的炔丙基酯中获得）来获得。只要Meerwein试剂用于促进苯甲酰胺功能的水解。可以使用两步序列制备各种α-取代的甘氨酸盐，包括具有α-乙烯基和α-炔属功能的甘氨酸盐，包括阳离子甘氨酸合成子与各种有机镁试剂的缩合反应，然后进行水解。
• Oxazolidin-2-one-Pyrimidine Derivatives
  申请人：Fairhurst Robin Alec

  公开号：US20140135330A1

  公开（公告）日：2014-05-15

  The present invention relates to oxazolidin-2-one substituted pyrimidine compounds that act as PI3K (phosphatidylinositol-3-kinase) inhibitors, as well as pharmaceutical compositions thereof, methods for their manufacture and uses for the treatment of conditions, diseases and disorders dependent on PI3K.

  本发明涉及取代嘧啶的噁唑烷-2-酮化合物，其作为PI3K（磷脂酰肌醇-3-激酶）抑制剂，以及其药用组合物、制备方法和用于治疗依赖于PI3K的疾病、症状和疾病的用途。
• Syntheses of Optically Active, Protected and Unprotected Vinylglycines.
  作者：Taisuke ITAYA、Shigeyuki SHIMIZU、Satoshi NAKAGAWA、Masatoshi MORISUE

  DOI：10.1248/cpb.42.1927

  日期：——

  Vinylglycine (2) has been shown to undergo racemization under acidic conditions. Optically pure 2 was obtained from 2·HCl by enzymatic hydrolysis through N-acetylvinylglycine (5), followed by recrystallization. (S)-N-(Methoxycarbonyl)vinylglycine (6) was configurationally so unstable under acidic conditions that 6 could not be obtained from 2 in an optically pure form. On the other hand, configurationally stable (S)-N-(9-phenylfluoren-9-yl)vinylglycine methyl ester (9) was synthesized from (S)-homoserine; 9 was hydrolyzed with sodium hydroxide to afford the carboxylic acid 10 of more than 99% ee.

  乙烯基甘氨酸（2）在酸性条件下会发生消旋化。通过酶水解 N-乙酰乙烯基甘氨酸 (5)，然后重结晶，从 2-HCl 中得到了光学纯度为 2 的乙烯基甘氨酸。(在酸性条件下，(S)-N-（甲氧羰基）乙烯基甘氨酸（6）的构型非常不稳定，因此无法从 2 中得到光学纯的 6。另一方面，从(S)-高丝氨酸合成了构型稳定的(S)-N-(9-苯基芴-9-基)乙烯基甘氨酸甲酯(9)。