5-(tert-butoxycarbonylamino)pent-2-ynoic acid | 1175621-48-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5-(tert-butoxycarbonylamino)pent-2-ynoic acid
• 英文别名: 5-{[(Tert-butoxy)carbonyl]amino}pent-2-ynoicacid；5-[(2-methylpropan-2-yl)oxycarbonylamino]pent-2-ynoic acid
• CAS: 1175621-48-3
• 化学式: C₁₀H₁₅NO₄
• 分子量: 213.233
• InChiKey: IIUCWHQBKUDVFC-UHFFFAOYSA-N

物化性质

• 沸点：
  388.2±25.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(tert-butoxycarbonylamino)pent-2-ynoic acid 在 4-二甲氨基吡啶 、 silver hexafluoroantimonate 、 三苯基膦氯金 、 碳酸氢钠 、 N,N'-二异丙基碳二亚胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 2.25h， 生成 9-(2-aminoethyl)-2,3,6,7-tetrahydro-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizin-11-one
  参考文献：
  名称：

  Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

  摘要：

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.

  DOI：

  10.1021/jo3006842
• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-N-but-3-ynyl-4-methylbenzenesulfonamide 在 甲醇 、 甲基锂 、 magnesium 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 4.5h， 生成 5-(tert-butoxycarbonylamino)pent-2-ynoic acid
  参考文献：
  名称：

  Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents

  摘要：

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.

  DOI：

  10.1021/jo3006842

文献信息

• Molecular Design of SERTlight: A Fluorescent Serotonin Probe for Neuronal Labeling in the Brain
  作者：Wei-Li Lee、Xavier Westergaard、Christopher Hwu、Jennifer Hwu、Tomas Fiala、Clay Lacefield、Umed Boltaev、Adriana M. Mendieta、Lisa Lin、Mark S. Sonders、Keaon R. Brown、Keer He、Wesley B. Asher、Jonathan A. Javitch、David Sulzer、Dalibor Sames

  DOI：10.1021/jacs.3c11617

  日期：2024.4.10

  molecule fluorescent agent, termed SERTlight, that specifically labels serotonergic neuronal cell bodies, dendrites, and axonal projections as a serotonin transporter (SERT) fluorescent substrate. SERTlight was developed by an iterative molecular design process, based on an aminoethyl-quinolone system, to integrate structural elements that impart SERT substrate activity, sufficient fluorescent brightness

  血清素能递质系统在神经系统的神经传递、突触可塑性、病理过程以及抗抑郁药和迷幻药的治疗效果以及胃肠道和循环系统中发挥着重要作用。我们引入了一种新型小分子荧光剂，称为SERTlight ，它专门标记血清素能神经元细胞体、树突和轴突投射作为血清素转运蛋白 (SERT) 荧光底物。 SERTlight 是通过基于氨基乙基喹诺酮系统的迭代分子设计过程开发的，整合了赋予 SERT 底物活性、足够的荧光亮度和广泛缺乏药理活性的结构元素，包括血清素（5-羟色胺，5HT）受体、其他 G 蛋白偶联受体 (GPCR)、离子通道和单胺转运蛋白。高标记选择性不是通过与 SERT 本身的高亲和力结合来实现的，而是通过 SERT 介导的 SERTlight 的足够速率的运输来实现，导致这些分子在 5HT 神经元中积累，并在哺乳动物大脑中产生强大的选择性光学信号。 SERTlight 提供稳定的信号，因为它不是通过胞吐作用释放的，也不是通过
• [EN] COMPOUNDS SELECTIVE FOR JAK1 AND METHODS OF USE<br/>[FR] COMPOSÉS SÉLECTIFS POUR JAK1 ET PROCÉDÉS D'UTILISATION
  申请人：[en]VIVIDION THERAPEUTICS, INC.

  公开号：WO2022251280A1

  公开（公告）日：2022-12-01

  Disclosed herein are compounds selective for JAK1, pharmaceutical compositions comprising said compounds, and methods of using said compounds.
• Catalytic Coupling of Arene C–H Bonds and Alkynes for the Synthesis of Coumarins: Substrate Scope and Application to the Development of Neuroimaging Agents
  作者：Paul A. Vadola、Dalibor Sames

  DOI：10.1021/jo3006842

  日期：2012.9.21

  C-H bond functionalization offers strategically novel approaches to complex organic compounds. However, many C-H functionalization reactions suffer from poor compatibility with Lewis basic functional groups, especially amines, which are often essential for biological activity. This study describes a systematic examination of the substrate scope of catalytic hydroarylation in the context of complex amino coumarin synthesis. The choice of substrates was guided by the design and development of the next generation of fluorescent false neurotransmitters (FFNs), neuroimaging probes we recently introduced for optical imaging of neurotransmission in the brain. Comparison of two mild protocols using catalytic PtCl4 or Au(PPh3)Cl/AgSbF6 revealed that each method has a broad and mutually complementary substrate scope. The relatively less active platinum system out-performed the gold catalyst with indole substrates lacking substitution at the C-3 position and provided higher regioselectivity in the case of carbazole-based substrates. On the other hand, the more active gold catalyst demonstrated excellent functional group tolerance, and the ability to catalyze the formation of strained, helical products. The development of these two protocols offers enhanced substrate scope and provides versatile synthetic tools required for the structure-activity examination of FFN neuroimaging probes as well as for the synthesis of complex coumarins in general.