(1R,6S)-bicyclo[4.3.1]decan-8-one | 373639-54-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,6S)-bicyclo[4.3.1]decan-8-one
• 英文别名: (1S,6R)-bicyclo[4.3.1]decan-8-one
• CAS: 373639-54-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: QEFLRRDCPNUYBA-DTORHVGOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (1R,6S)-bicyclo[4.3.1]decan-8-one 在 Amberlyst 15 、 4 A molecular sieve 、 lithium diisopropyl amide 、 儿萘酚硼烷 作用下， 以 四氢呋喃 、 甲醇 、 四氯化碳 、 正己烷 、 氯仿 、 甲苯 为溶剂， 反应 53.83h， 生成 (1S,6R,10R)-(+)-6-Methyl-4-oxabicyclo[8.4.1]pentadecan-3-one
  参考文献：
  名称：

  Constructing Conformationally Constrained Macrobicyclic Musks

  摘要：

  To investigate the structure odor correlation of musks,(12R)-12-methyl-13-tridecanotide (1), a macrocyclic musk, and 13-tridecanolide. its non-musky demethyl analogue. were conformationally constrained by introduction of methylene bridges between C-3 and C-8 or C-9. These [7.5.1]- and [8.4.1]macrobicycles were synthesized starting from bicyclo[5.3.1]undec-8-en-9-one (3) and bicyclo[4.3.1]dec-7-en-8-one (8), respectively, by a sequence consisting of catalytic hydrogenation. a-alkylation with a TBS-protected (tert-butyldimethylsilyl) hydroxy halide., acid-catalyzed cyclization, oxidative cleavage of the formed enol ether double bond, and subsequent reduction of the carbonyl group via its tosylhydrazone. The compound (1R,6R,9R)-(+)-6-methyl-4-oxa-bicyclo[7.5.1]pentadecan-3-one (22) was found to possess the most pronounced musk odor, and this was rationalized by a superposition analysis with the polycyclic aromatic musk odorant (4S,7R)-Galaxolide (2). In its (1S,6R,9S)-(+)stereoisomer-23 as well as in (1S,6R, 10R)-(+)-6-methyl-4-oxabicyclo-[8.4.1]pentadecan-3-one (18) the (6R)-methyl group seems to hinder the interaction with the musk receptor, while the demethyl compounds 7 and 12 showed only very faint odors.

  DOI：

  10.1002/1521-3765(20010803)7:15<3254::aid-chem3254>3.0.co;2-#
• 作为产物：
  描述：

  2-环庚烯-1-酮 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 、 苯甲醇 为溶剂， 25.0~90.0 ℃ 、405.3 kPa 条件下， 反应 12.0h， 生成 (1R,6S)-bicyclo[4.3.1]decan-8-one
  参考文献：
  名称：

  Momose, T.; Masuda, K.; Muraoka, O., Synthetic Communications, 1984, vol. 14, # 6, p. 493 - 500

  摘要：

  DOI：

文献信息

• SUBSTITUTED BENZIMIDAZOLE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF
  申请人：Shionogi & Co., Ltd.

  公开号：US20140187535A1

  公开（公告）日：2014-07-03

  The disclosure relates to Substituted Benzimidazole-Type Piperidine Compounds of Formula (I): and pharmaceutically acceptable salts or solvates thereof, e.g., a pharmaceutically acceptable salt or solvate, wherein R 1 , R 2 , R 3 , Q a , W, U, A, B, Z, a, and the dashed lines are as defined herein, compositions comprising an effective amount of a Substituted Benzimidazole-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Substituted Benzimidazole-Type Piperidine Compound.

  该披露涉及式(I)的取代苯并咪唑基哌啶化合物及其药学上可接受的盐或溶剂，例如药学上可接受的盐或溶剂，其中R1、R2、R3、Qa、W、U、A、B、Z、a和虚线如本文所定义，包括有效量的取代苯并咪唑基哌啶化合物的组合物，以及治疗或预防疾病的方法，例如疼痛，包括向需要的动物施用有效量的取代苯并咪唑基哌啶化合物。
• Total Synthesis of (±)-Lycojaponicumin D and Lycodoline-Type <i>Lycopodium</i> Alkaloids
  作者：Xian-He Zhao、Qing Zhang、Ji-Yuan Du、Xin-Yun Lu、Ye-Xing Cao、Yu-Hua Deng、Chun-An Fan

  DOI：10.1021/jacs.7b03280

  日期：2017.5.24

  Lycopodium alkaloids with structural diversity and biological significance have been stimulating an increasing interest in the synthetic and medicinal communities, in which inspiration and exploration of their related biogenetic relationship generally constitute one of the major concerns. Driven by the plausible biogenetic entry to lycojaponicumin D as the first member of Lycopodium alkaloids having

  具有结构多样性和生物学意义的石蒜生物碱一直引起人们对合成和药用群落的兴趣，在这些领域中，与它们相关的生物遗传关系的启发和探索通常是主要关注的问题之一。通过合理的生物基因条目lycojaponicumin d随着第一构件驱动石松具有结构上不常见的C3–C13连接支架的生物碱，与lycodoline的新连接已被提出，并且是在前所未有的生物启发的串联断裂/曼尼希反应设计的基础上发现的。通过在[3.3.1]双环lycodoline双环系统中快速组装桥头异官能团而启动了一种新的串联钯介导的氧化脱氢/杂-迈克尔反应，用于应变驱动的C-杂原子键的形成，从而导致构象刚性桥头杂四元碳的新方法。本统一战略为九种天然石蒜的不同总合成提供了一个方案 生物碱和4种非天然C12差向异构体，其中（±）-石蒜素D和6种石蒜碱类生物碱是首次人工合成。
• OXIME-SUBSTITUTED-QUINOXALINE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF
  申请人：Shionogi & Co., Ltd.

  公开号：US20140187544A1

  公开（公告）日：2014-07-03

  The present disclosure relates to Oxime-Substituted Quinoxaline-Type Piperidine Compounds, such as those of Formula (I): and the pharmaceutically acceptable salts and solvates thereof, wherein R 1 , R 2 , R 3 , R 4 , R 20 , R 21 , Q, Y 1 , Z, A, B, and a are as defined herein; compositions comprising an effective amount of an Oxime-Substituted Quinoxaline-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of an Oxime-Substituted Quinoxaline-Type Piperidine Compound.

  本公开涉及氧肟取代的喹喔啉型哌啶化合物，例如公式（I）中的化合物及其药用可接受的盐和溶剂化合物，其中R1、R2、R3、R4、R20、R21、Q、Y1、Z、A、B和a如本文所定义；包含有效量氧肟取代的喹喔啉型哌啶化合物的组合物，以及治疗或预防疾病的方法，例如疼痛，包括向需要治疗的动物施用有效量的氧肟取代的喹喔啉型哌啶化合物。
• [EN] QUINAZOLIN-4(3H)-ONE-TYPE PIPERIDINE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE PIPÉRIDINE DU TYPE QUINAZOLIN-4(3H)-ONE ET UTILISATIONS DE CEUX-CI
  申请人：PURDUE PHARMA LP

  公开号：WO2014102589A1

  公开（公告）日：2014-07-03

  The present disclosure relates to Quinazolin-4(3H)-one-Type Piperidine Compounds, such as those of Formule (I) and the pharmaceutically acceptable salts and solvates thereof, wherein R1, R2, R3, Q, Y1, Z, A, B, E, and a are as defined herein; compositions comprising an effective amount of a Quinazolin-4(3H)-one-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of a Quinazolin-4(3 H)-one-Type Piperidine Compound.

  本公开涉及喹唑啉-4(3H)-酮型哌啶化合物，例如公式(I)中的化合物及其药学上可接受的盐和溶剂，其中R1、R2、R3、Q、Y1、Z、A、B、E和a如本文所定义；包含有效量喹唑啉-4(3H)-酮型哌啶化合物的组合物；以及治疗或预防疼痛等疾病的方法，包括向需要的动物施用有效量喹唑啉-4(3H)-酮型哌啶化合物。
• OXIME-SUBSTITUTED QUINOXALINE-TYPE PIPERIDINE COMPOUNDS AS ORL-1 MODULATORS
  申请人：Purdue Pharma L.P.

  公开号：US20150238485A1

  公开（公告）日：2015-08-27

  The present disclosure relates to Oxime-Substituted Quinoxaline-Type Piperidine Compounds, such as those of Formula (I): and the pharmaceutically acceptable salts and solvates thereof, wherein R 1 , R 2 , R 3 , R 4 , R 20 , R 21 , Q, Y 1 , Z, A, B, and a are as defined herein; compositions comprising an effective amount of an Oxime-Substituted Quinoxaline-Type Piperidine Compound, and methods to treat or prevent a condition, such as pain, comprising administering to an animal in need thereof an effective amount of an Oxime-Substituted Quinoxaline-Type Piperidine Compound.

  本公开涉及肟取代的喹噁啉型哌啶化合物，例如式（I）中的化合物及其药学上可接受的盐和溶剂化合物，其中R1、R2、R3、R4、R20、R21、Q、Y1、Z、A、B和a如本文所定义；包含有效量肟取代的喹噁啉型哌啶化合物的组合物，以及治疗或预防疾病（如疼痛）的方法，包括向需要治疗的动物中有效量的肟取代的喹噁啉型哌啶化合物。