(3-吡咯烷-1-基苯基)甲醇 | 859850-72-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 中文名称: (3-吡咯烷-1-基苯基)甲醇
• 中文别名: (3-吡啶基苯基)甲醇
• 英文名称: (3-(pyrrolidin-1-yl)phenyl)methanol
• 英文别名: (3-Pyrrolidin-1-ylphenyl)methanol
• CAS: 859850-72-9
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: MYIYSGIMXUQECR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3-吡咯烷-1-基苯基)甲醇 在 氯化亚砜 、 potassium carbonate 、 potassium iodide 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 8.0h， 生成 2-(6-(3-(pyrrolidine-1-yl)benzyloxy)-2,3-dihydro-1-benzofuran-3-yl)acetic acid
  参考文献：
  名称：

  Discovery of novel pyrrole-based scaffold as potent and orally bioavailable free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

  摘要：

  The free fatty acid receptor 1 (FFA1) has gained significant interest as a novel antidiabetic target. Most of FFA1 agonists reported in the literature bearing a common biphenyl scaffold, which was crucial for toxicity verified by the researchers of Daiichi Sankyo. Herein, we describe the systematic exploration of non-biphenyl scaffold and further chemical modification of the optimal pyrrole scaffold. All of these efforts led to the identification of compound 11 as a potent and orally bioavailable FFA1 agonist without the risk of hypoglycemia. Further molecular modeling studies promoted the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.014
• 作为产物：
  描述：

  3-碘苯甲酸甲酯 在 sodium tetrahydroborate 、 copper(l) iodide 、 potassium carbonate 、 L-脯氨酸 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 (3-吡咯烷-1-基苯基)甲醇
  参考文献：
  名称：

  Discovery of novel pyrrole-based scaffold as potent and orally bioavailable free fatty acid receptor 1 agonists for the treatment of type 2 diabetes

  摘要：

  The free fatty acid receptor 1 (FFA1) has gained significant interest as a novel antidiabetic target. Most of FFA1 agonists reported in the literature bearing a common biphenyl scaffold, which was crucial for toxicity verified by the researchers of Daiichi Sankyo. Herein, we describe the systematic exploration of non-biphenyl scaffold and further chemical modification of the optimal pyrrole scaffold. All of these efforts led to the identification of compound 11 as a potent and orally bioavailable FFA1 agonist without the risk of hypoglycemia. Further molecular modeling studies promoted the understanding of ligand-binding pocket and might help to design more promising FFA1 agonists. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2016.03.014

文献信息

• Stereodivergent Synthesis of Enantioenriched 2,3-Disubstituted Dihydrobenzofurans via a One-Pot C–H Functionalization/Oxa-Michael Addition Cascade
  作者：Dong-Xing Zhu、Jian-Guo Liu、Ming-Hua Xu

  DOI：10.1021/jacs.1c03498

  日期：2021.6.16

  A one-pot rhodium-catalyzed C–H functionalization/organocatalyzed oxa-Michael addition cascade reaction has been developed. This methodology enables the stereodivergent synthesis of diverse 2,3-disubstituted dihydrobenzofurans with broad functional group compatibility in good yields with high levels of stereoselectivity under exceptionally mild conditions. The full complement of stereoisomers of chiral

  已经开发了一种一锅铑催化的 C-H 官能化/有机催化的氧杂-迈克尔加成级联反应。该方法能够在极其温和的条件下以良好的收率和高立体选择性合成具有广泛官能团兼容性的多种 2,3-二取代二氢苯并呋喃。通过两种手性催化剂的适当排列，可以随意获得手性 2,3-二取代二氢苯并呋喃和 3,4-二取代异色满的完整立体异构体。目前的工作提供了一个罕见的例子，即两种手性催化剂在一次操作中通过两步反应独立控制两个连续的立体中心。
• [EN] NITROGEN-CONTAINING FUSED HETEROCYCLIC COMPOUNDS AND THEIR USE AS BETA AMYLOID PRODUCTION INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES CONDENSÉS CONTENANT DE L'AZOTE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PRODUCTION DE LA BÊTA-AMYLOÏDE
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2010098487A1

  公开（公告）日：2010-09-02

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的分子式为[I]：或其药理学可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似于非芳香环基团的融合物，可以被取代，环B代表一个苯基或类似的基团，可以被取代，X1代表一个单键或类似物，R1和R2分别代表一个C1-6烷基基团或类似物，m表示0到3的整数，n表示0到2的整数，对由Aβ引起的疾病具有治疗作用。
• Regiospecific and Enantioselective Arylvinylcarbene Insertion of a C–H Bond of Aniline Derivatives Enabled by a Rh(I)-Diene Catalyst
  作者：Dong-Xing Zhu、Hui Xia、Jian-Guo Liu、Lung Wa Chung、Ming-Hua Xu

  DOI：10.1021/jacs.0c13191

  日期：2021.2.17

  C–H bond for direct enantioselective C(sp2)-H functionalization of aniline derivatives catalyzed by a rhodium(I)-diene complex was developed for the first time. The reaction occurred exclusively at the uncommon vinyl terminus site with excellent E selectivity and enantioselectivities, providing various chiral γ,γ-gem-diarylsubstituted α,β-unsaturated esters with broad functional group compatibility

  首次开发了将芳基乙烯基类胡萝卜素不对称地插入C–H键中，以使铑（I）-二烯络合物催化苯胺衍生物的直接对映选择性C（sp 2）-H功能化。该反应仅在不常见的乙烯基末端发生，具有出色的E选择性和对映选择性，提供各种手性γ，γ-宝石-二芳基取代的α，β-不饱和酯，在简单温和的条件下具有广泛的官能团相容性。它提供了具有选择性乙烯基反应性的芳烃不对称C–H插入的罕见例子。该协议的综合应用具有多种通用的产品转换功能。还进行了系统的DFT计算，以阐明Rh（I）催化的C（sp 2）-H功能化反应的不常见对映选择性和区域选择性的反应机理和起源。测量和计算出的氘氘动力学同位素反演效应支持速率决定步骤的C–C键形成步骤。还提出了手性配体与底物之间的有吸引力的相互作用，以控制对映选择性。
• Substituted alkylamine derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05234946A1

  公开（公告）日：1993-08-10

  The substituted alkylamine derivatives represented by formula (I) ##STR1## wherein R.sup.1 represents (a) substituted or unsubstituted C.sub.2-6 alkenyl group, (b) substituted or unsubstituted C.sub.3-6 cycloalkenyl group, (c) substituted or unsubstituted C.sub.2-6 alkynyl group, (d) substituted or unsubstituted aryl group, (e) substituted or unsubstituted heterocyclic group, (f) fused heterocyclic group which may be substituted, or (g) group represented by the formula Ru.sup.11 -Ar wherein R.sup.11 is a heterocyclic group and Ar is a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and which may be substituted; ##STR2## represents a 5- or 6-membered aromatic ring which may contain a hetero N, O or S atom, and may be substituted by R.sup.7, X and Y are linking groups, R.sup.2 is H or lower alkyl, R.sup.3 is hydrogen, lower alkyl, lower alkenyl, lower alkynyl or lower cycloalkyl, R.sup.4 and R.sup.5 are independently hydrogen or halogen atoms, R.sup.6 represents (a) substituted or unsubstituted acyclic hydrocarbon group which may be unsaturated, (b) substituted or unsubstituted cycloalkyl group, or (c) substituted or unsubstituted phenyl group, or non-toxic salts thereof. (E)-N-(6-6-dimethyl-2-hepten-4-ynyl)-N-ethyl-3-[4-(3-thienyl)-2-thienyl-me thyloxy]benzylamine hydrochloride is a representative example. The substituted alkylamine derivatives are useful as pharmaceuticals, particularly for the treatment and prevention of hypercholesterolemia, hyperlipemia and arteriosclerosis.

  公式（I）所代表的取代基烷基胺衍生物，其中R1代表（a）取代或未取代的C2-6烯丙基基团，（b）取代或未取代的C3-6环烯基基团，（c）取代或未取代的C2-6炔基基团，（d）取代或未取代的芳基基团，（e）取代或未取代的杂环基团，（f）可能被取代的融合杂环基团，或（g）由Ru11-Ar表示的基团，其中R11是杂环基团，Ar是5-或6-成员芳香环，可以含有杂原子N、O或S，且可以被取代；表示5-或6-成员芳香环，可以含有杂原子N、O或S，可以被R7取代，X和Y是连接基团，R2是H或较低的烷基，R3是氢、较低的烷基、较低的烯丙基、较低的炔基或较低的环烷基，R4和R5独立地表示氢或卤素原子，R6表示（a）取代或未取代的非环烷基，可以不饱和，（b）取代或未取代的环烷基，或（c）取代或未取代的苯基，或其非毒性盐。 （E）-N-（6-6-二甲基-2-庚烯-4-炔基）-N-乙基-3- [4-（3-噻吩基）-2-噻吩基]甲氧基]苯基胺盐酸盐是一个代表性的例子。这些取代基烷基胺衍生物可用作药物，特别是用于治疗和预防高胆固醇血症、高脂血症和动脉硬化。
• Nitrogen-Containing Fused Heterocyclic Compounds and Their use as Beta Amyloid Production Inhibitors
  申请人：Kitazawa Noritaka

  公开号：US20120053171A1

  公开（公告）日：2012-03-01

  A compound represented by the formula [I]: or a pharmacologically acceptable salt or ester thereof, wherein Ring A represents a five-membered aromatic heterocyclic group or the like fused with a non-aromatic ring group, which may be substituted, Ring B represents a phenyl group or the like which may be substituted, X1 represents a single bond or the like, R1 and R2 each represent a C1-6 alkyl group or the like, m represents an integer of 0 to 3, and n represents an integer of 0 to 2, is effective as a therapeutic agent for a disease caused by Aβ.

  化合物的化学式为[I]，或其药理学上可接受的盐或酯，其中环A代表一个五元芳香杂环基团或类似物，与非芳香环基团融合，可以被取代，环B代表苯基或类似物，可以被取代，X1代表单键或类似物，R1和R2各代表C1-6烷基或类似物，m代表0至3的整数，n代表0至2的整数，该化合物对由Aβ引起的疾病具有治疗作用。