N-{(R,S)-9-methyl-1,4-dioxaspiro[4.5]decan-8-yliden}-(R)-1-phenylethylamine | 372955-64-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-{(R,S)-9-methyl-1,4-dioxaspiro[4.5]decan-8-yliden}-(R)-1-phenylethylamine
• CAS: 372955-64-1
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: YAEKZZYVNOGDTA-IAAANQJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-{(R,S)-9-methyl-1,4-dioxaspiro[4.5]decan-8-yliden}-(R)-1-phenylethylamine 在 水 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 99.0h， 生成 [1R]-1-methyl-1(3-pentanone)-3-ethylenedioxy-2-oxocyclohexanone
  参考文献：
  名称：

  Asymmetric synthesis of 3β-angeloyloxy-4β-hydroxyeudesman-8-one, purported sesquiterpene from Pluchea quitoc †

  摘要：

  3β-桉油烯氧基-4β-羟基桉烷-8-酮，据称是从羽芒菊地上部分分离出的物质，经由一条明确的立体控制途径合成，并发现其与天然产物不同。

  DOI：

  10.1039/a909112b
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 为溶剂， 反应 16.5h， 生成 N-{(R,S)-9-methyl-1,4-dioxaspiro[4.5]decan-8-yliden}-(R)-1-phenylethylamine
  参考文献：
  名称：

  Enantioselective imine Michael reaction for the preparation of the (8′R,8a′S)-8,8a′-dimethyl-1′,3′,4′,7′,8′,8a′-hexahydrospiro[1,3-dioxolane-2,2′(6′H)naphthalen]-6′-one building block. A formal synthesis of (+)-valencenol

  摘要：

  The enantioselective Michael addition of a chiral imine of 4-protected 2-methylcyclohexane-1,4-dione to phenyl crotonate led after cyclization. to the corresponding bicyclic lactam. Reductive cleavage of the chiral moiety followed by saponification gave the corresponding keto-acid, which was cyclized to afford a lactone. Belleau-Fujimoto reaction of the lactone then led to the title building block (diastereoselectivity 96:4, e.e. > 98%) in 11% overall yield from the starting dione. (8R, 8aS)-(+)-8,8a-Dimethyl-3,4,6,7,8,8a-hexahydronaphthalen-2 (1H)-one was obtained after reduction of the carbonyl group, acetylation, and reductive cleavage-deprotection (52% overall yield), representing a formal synthesis of (+)-valencenol. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00289-0

文献信息

• [EN] TETRAHYDRONAPHTHALENE DERIVATIVES USEFUL AS NRF2 ACTIVATORS<br/>[FR] DÉRIVÉS DE TÉTRAHYDRONAPHTALÈNE UTILES EN TANT QU'ACTIVATEURS DE NRF2
  申请人：BIOGEN MA INC

  公开号：WO2019104030A1

  公开（公告）日：2019-05-31

  Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, and methods for their use as Nrf2 activators and for their production.

  提供的是I式化合物，或其药用可接受的盐，以及它们作为Nrf2激活剂的使用方法和生产方法。
• A Convenient Synthesis of Chiral, Non-Racemic [4<i>a</i>S,8<i>a</i>R]-5,5,8a-Trimethyl Octahydro-2,2-(1,3-Dioxolane)-Naphthalene
  作者：Beatriz S.M. Tenius、Evelyn K. Schroeder

  DOI：10.1080/00397910008087164

  日期：2000.4

  Abstract (-)-(4aS,8aR)-5,5-8a-trimethyl-trans-decaline 1 was prepared in a stereoespecific synthesis of 4 steps and 38% yield. The key-step involves an asymmetric Robinson annulation via Michael addition of chiral imine.

  摘要 (-)-(4aS,8aR)-5,5-8a-trimethyl-trans-decaline 1 是通过立体定向合成 4 步和 38% 的收率制备的。关键步骤涉及通过手性亚胺的迈克尔加成进行不对称罗宾逊环化。
• Tetrahydronaphthalene derivatives useful as Nrf2 activators
  申请人：BIOGEN MA INC.

  公开号：US11465963B2

  公开（公告）日：2022-10-11

  Provided are compounds of Formula I, or pharmaceutically acceptable salts thereof, and methods for their use as Nrf2 activators and for their production.

  本文提供了式 I 的化合物或其药学上可接受的盐类，以及将它们用作 Nrf2 激活剂和生产它们的方法。
• Enantioselective synthesis of (2S4aS,8aR)-1,1,4a-trimethyldecahydronaphthalen-2-ol [(−)-TMD], (4aS,8aR)-5,5,8a-trimethyloctahydronaphthalen-2(1H)-one, and (−)-polywood®, through michael-type reaction of chiral imines
  作者：Ivan Jabin、Gilbert Revial、Karine Melloul、Michel Pfau

  DOI：10.1016/s0957-4166(97)00082-7

  日期：1997.4

  The title compounds 6, 15, and 17 have been synthesized in a straightforward way in good yields and high enantiomeric excesses by the chiral imines method, leading to building-blocks 2 and 10, followed by a few conventional steps. (C) 1997 Elsevier Science Ltd.
• Pfau, Michel; Jabin, Ivan; Revial, Gilbert, Journal of the Chemical Society. Perkin transactions I, 1993, # 17, p. 1935 - 1936
  作者：Pfau, Michel、Jabin, Ivan、Revial, Gilbert

  DOI：——

  日期：——