3-[(呋喃-2-甲基)-氨基]-1-丙醇 | 4439-22-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-[(呋喃-2-甲基)-氨基]-1-丙醇
• 英文名称: 2-((furan-2-ylmethyl)amino)ethan-1-ol
• 英文别名: 2-((furan-2-ylmethyl)amino)ethanol；2-(2-furylmethylamino)ethanol；2-furfurylamino-ethanol；2-Furfurylamino-aethanol；2-(furfurylamino)-ethanol；2-(furfurylamino)ethanol；2-[(2-Furylmethyl)amino]ethanol；2-(furan-2-ylmethylamino)ethanol
• CAS: 4439-22-9
• 化学式: C₇H₁₁NO₂
• mdl: MFCD07410475
• 分子量: 141.17
• InChiKey: PERSIOJMHRGFFY-UHFFFAOYSA-N

物化性质

• 沸点：
  123 °C(Press: 6 Torr)
• 密度：
  1.1184 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  45.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  3-[(呋喃-2-甲基)-氨基]-1-丙醇 在 盐酸 、 1-羟基-1H-苯并三唑铵盐 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(2-hydroxyethyl)-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide
  参考文献：
  名称：

  Discovery of 2-[1-(4,4-Difluorocyclohexyl)piperidin-4-yl]-6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118): A Potent, Orally Available, and Highly Selective PARP-1 Inhibitor for Cancer Therapy

  摘要：

  The nuclear protein poly(ADP-ribose) polymerase-1 (PARP-1) has a well-established role in the signaling and repair of DNA and is a prominent target in oncology, as testified by the number of candidates in clinical testing that unselectively target both PARP-1 and its closest isoform PARP-2. The goal of our program was to find a PARP-1 selective inhibitor that would potentially mitigate toxicities arising from cross-inhibition of PARP-2. Thus, an HTS campaign on the proprietary Nerviano Medical Sciences (NMS) chemical collection, followed by SAR optimization, allowed us to discover 2-[1-4,4-difluorocyclohexyl)piperidin-4-yl] -6-fluoro-3-oxo-2,3-dihydro-1H-isoindole-4-carboxamide (NMS-P118, 20by). NMS-P118 proved to be a potent, orally available, and highly selective PARP-1 inhibitor endowed with excellent ADME and pharmacokinetic profiles and high efficacy in vivo both as a single agent and in combination with Temozolomide in MDA-MB-436 and Capan-1 xenograft models, respectively. Cocrystal structures of 20by with both PARP-1 and PARP-2 catalytic domain proteins allowed rationalization of the observed selectivity.

  DOI：

  10.1021/acs.jmedchem.5b00680
• 作为产物：
  描述：

  糠醛肟 在 环氧乙烷 、 乙醇 、 溶剂黄146 、 锌 作用下， 生成 3-[(呋喃-2-甲基)-氨基]-1-丙醇
  参考文献：
  名称：

  Jur'ew; Sefirow, Zhurnal Obshchei Khimii, 1959, vol. 29, p. 2954,2956; engl. Ausg. S. 2916, 2919

  摘要：

  DOI：

文献信息

• Organocatalytic Enantioselective Synthesis of<i>P</i>-Stereogenic Chiral Oxazaphospholidines
  作者：Lanlan Wang、Zhijun Du、Qiang Wu、Rizhe Jin、Zheng Bian、Chuanqing Kang、Haiquan Guo、Xiaoye Ma、Lianxun Gao

  DOI：10.1002/ejoc.201600100

  日期：2016.4

  The enantioselective synthesis of P-stereogenic chiral organophosphines under organocatalysis is a challenging research field, and reports that use this approach are rare. Herein, we have developed the enantioselective synthesis of P-stereogenic chiral oxazaphospholidines by using a bicyclic thiazole as the organocatalyst in the P–N and P–O bond-forming reaction. The P-chiral products were prepared

  在有机催化下对映选择性合成 P-立体手性有机膦是一个具有挑战性的研究领域，使用这种方法的报道很少。在此，我们通过使用双环噻唑作为 P-N 和 P-O 键形成反应中的有机催化剂，开发了对映选择性合成 P-立体手性 oxazaphosphollides。P-手性产物以高产率制备，对映选择性适中。该过程中使用的碱对反应的对映选择性有显着影响，在某些情况下会导致 P-手性中心的相反构型。
• Chemokine receptor binding heterocyclic compounds
  申请人：AnorMED, Inc.

  公开号：US06750348B1

  公开（公告）日：2004-06-15

  This invention relates to a novel class of heterocyclic compounds that bind chemokine receptors, inhibiting the binding of their natural ligands thereby. These compounds result in protective effects against infection by HIV through binding to chemokine receptors, including CXCR4 and CCR5, thus inhibiting the subsequent binding by these chemokines. The present invention provides a compound of Formula I wherein, W is a nitrogen atom and Y is absent or, W is a carbon atom and Y═H; R1 to R7 may be the same or different and are independently selected from hydrogen or straight, branched or cyclic C1-6 alkyl; R8 is a substituted heterocyclic group or a substituted aromatic group Ar is an aromatic or heteroaromatic ring each optionally substituted at single or multiple, non-linking positions with electron-donating or withdrawing groups; n and n′ are independently, 0-2; X is a group of the formula: Wherein, Ring A is an optionally substituted, saturated or unsaturated 5 or 6-membered ring, and P is an optionally substituted carbon atom, an optionally substituted nitrogen atom, sulfur or oxygen atom. Ring B is an optionally substituted 5 to 7-membered ring. Ring A and Ring B in the above formula can be connected to the group W from any position via the group V, wherein V is a chemical bond, a (CH2)n″ group (where n″=0-2) or a C═O group. Z is, (1) a hydrogen atom, (2) an optionally substituted C1-6 alkyl group, (3) a C0-6 alkyl group substituted with an optionally substituted aromatic or heterocyclic group, (4) an optionally substituted C0-6 alkylamino or C3-7 cycloalkylamino group, (5) an optionally substituted carbonyl group or sulfonyl. These compounds further include any pharmaceutically acceptable acid addition salts and metal complexes thereof and any stereoisomeric forms and mixtures of stereoisomeric forms thereof.

  这项发明涉及一类新型的杂环化合物，它们结合趋化因子受体，抑制其天然配体的结合。这些化合物通过结合趋化因子受体，包括CXCR4和CCR5，从而抑制这些趋化因子的后续结合，产生对HIV感染的保护效果。本发明提供了一个式I的化合物 其中，W是氮原子，Y不存在，或者W是碳原子，Y═H； R1至R7可以相同也可以不同，并且独立地选择自氢或直链、支链或环状的C1-6烷基； R8是一个取代的杂环基或取代的芳香基 Ar是一个芳香或杂芳环，每个环在单个或多个非连接位置可选择地取代有电子给体或吸引体基团； n和n′独立地为0-2； X是下式的一个基团： 其中，环A是一个可选择地取代的饱和或不饱和的5或6元环，P是一个可选择地取代的碳原子、一个可选择地取代的氮原子、硫或氧原子。环B是一个可选择地取代的5到7元环。上述式中的环A和环B可以通过基团V从任何位置连接到基团W，其中V是一个化学键，一个(CH2)n″基团（其中n″=0-2）或一个C═O基团。Z是(1)一个氢原子，(2)一个可选择地取代的C1-6烷基基团，(3)一个用可选择地取代的芳香或杂环基团取代的C0-6烷基基团，(4)一个可选择地取代的C0-6烷基氨基或C3-7环烷氨基基团，(5)一个可选择地取代的羰基或磺酰基。这些化合物还包括任何药学上可接受的酸盐和金属络合物，以及它们的任何立体异构体形式和立体异构体形式的混合物。
• Copper-Catalyzed Functionalizations of C₆₀ with Amino Alcohols
  作者：Hai-Tao Yang、Jie Ge、Xin-Wei Lu、Xiao-Qiang Sun、Chun-Bao Miao

  DOI：10.1021/acs.joc.7b00741

  日期：2017.6.2

  functionalizations of C60 with amino alcohols with aerobic oxygen as the sole oxidant have been explored. For 2-/3-amino alcohols, an aminooxygenation reaction occurs to generate fulleromorpholine and fullerooxazepane derivatives. When a tethered furan ring exists, a further intramolecular [4 + 2] reaction with the neighboring double bond occurs to furnish the cis-1 products. In the case of 4-/5-amino

  已经探索了CuI催化的C 60用氨基醇和好氧作为唯一氧化剂对C 60的各种官能化作用。对于2- / 3-氨基醇，发生氨基加氧反应以生成全氟吗啉和全氧恶唑烷衍生物。当存在束缚的呋喃环时，与相邻的双键发生进一步的分子内[4 + 2]反应以提供顺式-1产物。在4- / 5-氨基醇的情况下，通过环状烯胺中间体获得与环状酰胺连接的亚甲基富勒烯。
• Zinc-Catalyzed Esterification of <i>N</i> -β-Hydroxyethylamides: Removal of Directing Groups under Mild Conditions
  作者：Yuji Nishii、Takahiro Hirai、Sarah Fernandez、Paul Knochel、Kazushi Mashima

  DOI：10.1002/ejoc.201700748

  日期：2017.9.15

  Amide transformations involving C-N bond cleavage are recognized as difficult reactions owing to the inert nature of amides resulting from resonance. Accordingly, a strong inductive effect and geometrical distortion reasonably decrease the resonance stabilization to attenuate the C-N linkage. Although the conversion of such activated amides has been studied intensively, reaction systems for unactivated

  由于由共振引起的酰胺的惰性性质，涉及 CN 键断裂的酰胺转化被认为是困难的反应。因此，强感应效应和几何失真合理地降低了共振稳定性以衰减 CN 链接。尽管已经对此类活化酰胺的转化进行了深入研究，但未活化酰胺的反应体系尚未开发。我们在此报告了三氟甲磺酸锌 (II) [Zn(OTf)(2)] 催化剂在分子内酰基重排的帮助下实现了多种未活化的叔酰胺的酯化。该反应用于在温和的反应条件下一锅脱除各种酰胺基导向基团，以高产率得到相应的酯。
• Torii‐Type Electrosynthesis of α,β‐Unsaturated Esters from Furfurylated Ethylene Glycols and Amino Alcohols
  作者：Madara Darzina、Anna Lielpetere、Aigars Jirgensons

  DOI：10.1002/ejoc.202100605

  日期：2021.8.6

  Multifunctional building blocks were obtained by Torii-type ester electrosynthesis from biomass-derived furfural conjugates with ethylene glycols and amino alcohols. The products can be accessed by two consecutive electrochemical steps or by a one-pot procedure.

  通过鸟居式酯电合成从生物质衍生的糠醛缀合物与乙二醇和氨基醇中获得多功能结构单元。产品可以通过两个连续的电化学步骤或通过一锅程序获得。