5-Methoxy-2-indanol | 16513-64-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5-Methoxy-2-indanol
• 英文别名: 5-methoxyindan-2-ol；5-Methoxy-indan-2-ol；5-methoxy-2,3-dihydro-1H-inden-2-ol
• CAS: 16513-64-7
• 化学式: C₁₀H₁₂O₂
• 分子量: 164.204
• InChiKey: QSZOBKZTEZYQOJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-Methoxy-2-indanol 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.75h， 生成 5-Methoxyindan-2-yl-methansulfonate
  参考文献：
  名称：

  Synthesis and asymmetric resolution of a dopaminergic compound: 2-amino-5-methoxyindane

  摘要：

  The racemic synthesis and subsequent resolution of 2-amino-5-methoxyindane enantiomers were achieved starting from 5-bromoindan-2-ol in six steps with 38% total yield. The first step involved the substitution of the Br atom by using NaOMe in the presence of CuI to afford 5-methoxyindan-2-ol. The OH group of 5-methoxyindan-2-ol was converted into its mesylate ester, which was converted into the corresponding azide by reaction with sodium azide. The Pd C-catalyzed hydrogenation of the azide functional group in the presence of CHCI3, followed by neutralization of the amine hydrochloride salt with NaOH, furnished the rac-2-amino-5-methoxyindane. Next, rac-2-amino-5-methoxyindane was converted into its diastereomeric amide derivatives by reaction with (R)-mandeloyl chloride. The diastereomeric amide mixture was separated by recrystallization to give the (R,S)- and (R,R)-diastereomers. The absolute configuration of the (R,S)-isomer was determined by X-ray crystallography. The hydrolysis of these diastereomers gave (R)- and (S)-2-amino-5-methoxyindane with high enantiopurity. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.04.005
• 作为产物：
  描述：

  acetic acid 5-acetyl-indan-2-yl ester 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 生成 5-Methoxy-2-indanol
  参考文献：
  名称：

  Substituent effects on the chemical shifts of the bridge protons of benzonorbornenes

  摘要：

  在一系列6-取代苯基诺邻二环烯和苯基诺邻二烯中，对C₉桥上质子的化学位移进行了取代效应的研究，以及对5-取代2-茚醇中C₂质子的影响。这些效应与修正的Hammett关系τ_R - τ_H = ρ (σ_m + σ_p)/2呈线性相关。在苯基诺邻二烯中，从反式C₉质子获得的ρ值略微但显着大于从相应的顺式质子获得的值，而从顺-9-苯基诺邻醇和茚醇中获得的ρ值之间没有显著差异。较大的ρ_anti值可以解释为苯环的π-电子体系与桥碳的轨道体系之间的立体特异性电子相互作用。此外，结果表明上述修正的Hammett关系通常与苯环环烯和类似化合物的脂肪成分的取代效应具有良好的一致性。

  DOI：

  10.1139/v67-197

文献信息

• Isolation of a Major Metabolite (i-OHAP) of Aprindine and Its Identification as N-(3-(N,N-Diethylamino)propyl)-N-phenyl-2-aminoindan-5-ol.
  作者：Mikiko SHIMIZU、Kazuhiko TAKATORI、Masahiko KAJIWARA、Hiroyasu OGATA

  DOI：10.1248/bpb.21.530

  日期：——

  i-OHAP, a major metabolite of aprindine (AP), was isolated by TLC from rat feces and identified as N-[3-(N, N-diethylamino)propyl]-N-phenyl-2-aminoindan-5-ol, based on 1H-NMR, the H-H correlation spectroscopy (COSY) spectrum, MS and LC-MS. Its structure was also confirmed by comparison with the synthesized compound. The hydroxy group of i-OHAP was located at the 5-position of the indan ring. AP is a prochiral compound, and the metabolism of AP to i-OHAP was stereoselective. The ratio of (+)/(-)-i-OHAP in rat feces and in human urine was about 5 and 15, respectively.

  i-OHAP 是阿普林定 (AP) 的主要代谢物，通过 TLC 从大鼠粪便中分离出来，并鉴定为 N-[3-(N,N-二乙基氨基)丙基]-N-苯基-2-氨基茚满-5-醇，基于 1H-NMR、H-H 相关光谱 (COSY) 光谱、MS 和 LC-MS。通过与合成化合物的比较也证实了其结构。 i-OHAP的羟基位于茚满环的5位。 AP是一种前手性化合物，AP向i-OHAP的代谢是立体选择性的。大鼠粪便和人尿液中(+)/(-)-i-OHAP的比率分别约为5和15。
• Substituted bicyclic derivatives and use thereof
  申请人：Matsumoto Akiko

  公开号：US20090054401A1

  公开（公告）日：2009-02-26

  [Object] To provide a compound having prostaglandin production-suppressing action and leukotriene production-suppressing action. [Means for Solution] A compound represented by the formula (I): [In the formula, represents a single bond, or a double bond, Link represents a single bond, or a saturated or unsaturated straight hydrocarbon having 1 or 2 carbon atoms, W represents a single bond, oxygen atom, sulfur atom, N(Rw) etc., Rw represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms etc, Rs represents -D-Rx etc., D represents a single bond, oxygen atom, sulfur atom etc., Rx represents a linear or branched saturated alkyl group having 3 to 8 carbon atoms etc., one of V 1 and V 2 represents Zx, and the other represents AR, Zx represents hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms etc., AR represents a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or heterocyclic ring, and Y represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms etc.], or a salt thereof.

  [目标] 提供一种具有前列腺素产生抑制作用和白三烯产生抑制作用的化合物。[解决方案] 一种由式(I)表示的化合物：[在式中，表示单键或双键，Link表示单键或具有1或2个碳原子的饱和或不饱和直链碳氢化合物，W表示单键、氧原子、硫原子、N(Rw)等，Rw表示氢原子、具有1至8个碳原子的烷基等，Rs表示-D-Rx等，D表示单键、氧原子、硫原子等，Rx表示具有3至8个碳原子的线性或支链饱和烷基等，V1和V2中的一个表示Zx，另一个表示AR，Zx表示氢原子、具有1至4个碳原子的线性或支链饱和烷基等，AR表示部分不饱和或完全不饱和的螺合环碳环或杂环，Y表示氢原子、具有1至4个碳原子的低烷基等。]，或其盐。
• SUBSTITUTED BICYCLIC CYCLIC DERIVATIVE AND USE THEREOF
  申请人：Asahi Kasei Pharma Corporation

  公开号：EP2006271A2

  公开（公告）日：2008-12-24

  [Object] To provide a compound having prostaglandin production-suppressing action and leukotriene production-suppressing action. [Means for solution] A compound represented by the formula (I): [In the formula, ---- represents a single bond, or a double bond, Link represents a single bond, or a saturated or unsaturated straight hydrocarbon having 1 or 2 carbon atoms, W represents a single bond, oxygen atom, sulfur atom, N(Rw) etc., Rw represents hydrogen atom, an alkyl group having 1 to 8 carbon atoms etc, Rs represents -D-Rx etc., D represents a single bond, oxygen atom, sulfur atom etc., Rx represents a linear or branched saturated alkyl group having 3 to 8 carbon atoms etc., one of V1 and V2 represents Zx, and the other represents AR, Zx represents hydrogen atom, a linear or branched saturated alkyl group having 1 to 4 carbon atoms etc., AR represents a partially unsaturated or completely unsaturated condensed bicyclic carbon ring or heterocyclic ring, and Y represents hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms etc.], or a salt thereof.

  [目的]提供一种具有抑制前列腺素生成作用和抑制白三烯生成作用的化合物。 [解决方法] 一种由式（I）表示的化合物： [式中，---- 代表单键或双键，Link 代表单键或具有 1 或 2 个碳原子的饱和或不饱和直链烃，W 代表单键、氧原子、硫原子、N(Rw)等，Rw 代表氢原子、具有 1 至 8 个碳原子的烷基等，Rs 代表-D-Rx 等，D 代表单键、氧原子、硫原子等、Rx 代表具有 3 至 8 个碳原子的直链或支链饱和烷基等，V1 和 V2 中的一个代表 Zx，另一个代表 AR，Zx 代表氢原子、具有 1 至 4 个碳原子的直链或支链饱和烷基等，AR 代表部分不饱和或完全不饱和的缩合双环碳环或杂环，Y 代表氢原子、具有 1 至 4 个碳原子的低级烷基等]，或其盐。
• US4975461A
  申请人：——

  公开号：US4975461A

  公开（公告）日：1990-12-04
• [EN] AMINOINDANE DERIVATIVES, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM, AND THEIR USE IN THERAPY<br/>[FR] DÉRIVÉS D'AMINOINDANE, COMPOSITIONS PHARMACEUTIQUES RENFERMANT CES DERNIERS ET UTILISATION DESDITS DÉRIVÉS EN THÉRAPIE
  申请人：ABBOTT GMBH & CO KG

  公开号：WO2012020131A2

  公开（公告）日：2012-02-16

  The present invention relates to aminoindane derivatives of the Formula (I) or a physiologically tolerated salt thereof. The invention relates to pharmaceutical compositions comprising such aminoindane deriva- tives, and the use of such aminoindane derivatives for therapeutic purposes. The aminoindane derivatives are GlyT1 inhibitors.