2-Allyloxymethyl-cyclohexanone | 201423-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Allyloxymethyl-cyclohexanone
• 英文别名: 2-[(Prop-2-en-1-yloxy)methyl]cyclohexanone；2-(prop-2-enoxymethyl)cyclohexan-1-one
• CAS: 201423-75-8
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: YVIHJCXQZKRWMD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Allyloxymethyl-cyclohexanone 在 三氢化钐 、 二碘甲烷 、 ClRh(PPh₃) 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醇 、 水 为溶剂， 生成 (1R,2R)-2-Hydroxymethyl-1-((E)-propenyl)-cyclohexanol
  参考文献：
  名称：

  碘化Sa（II）介导的连续的烷基-烯烃偶联/β-消除反应。

  摘要：

  碘化mar（II）（SmI（2））已用于分子内顺序的酮基-烯烃偶联/β消除反应。整个过程导致烯基物质净添加至酮羰基。该用于烯基部分的分子内递送的新颖方案避免了由烯基卤化镁和烯基锂试剂介导的亲核加成反应的典型基本反应条件。SmI（2）介导的过程中，由于最初的酮基-烯烃偶联反应具有出色的面部选择性，因此具有高度的立体控制能力。这些加成反应中引起的相对不对称诱导与更传统的亲核加成反应互补，因为烯基通过连接的系链被引导至羰基中心。

  DOI：

  10.1021/jo971889d
• 作为产物：
  描述：

  methyl 1,4-dioxaspiro[4.5]decane-6-carboxylate 在 盐酸 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 生成 2-Allyloxymethyl-cyclohexanone
  参考文献：
  名称：

  碘化Sa（II）介导的连续的烷基-烯烃偶联/β-消除反应。

  摘要：

  碘化mar（II）（SmI（2））已用于分子内顺序的酮基-烯烃偶联/β消除反应。整个过程导致烯基物质净添加至酮羰基。该用于烯基部分的分子内递送的新颖方案避免了由烯基卤化镁和烯基锂试剂介导的亲核加成反应的典型基本反应条件。SmI（2）介导的过程中，由于最初的酮基-烯烃偶联反应具有出色的面部选择性，因此具有高度的立体控制能力。这些加成反应中引起的相对不对称诱导与更传统的亲核加成反应互补，因为烯基通过连接的系链被引导至羰基中心。

  DOI：

  10.1021/jo971889d

文献信息

• NOVEL TRPA1 ANTAGONISTS
  申请人：Bilodeau Mark T.

  公开号：US20120196894A1

  公开（公告）日：2012-08-02

  The present invention relates to compositions and methods that modulate at least one TRP family member. Specifically, the present invention relates to novel TRPA1 antagonists and their use in the treatment of pain such as chronic inflammatory and neuropathic pain. Compounds that can modulate one or more TRPA1 functions are useful in many aspects including, but not limited to, maintaining calcium homeostasis; maintaining sodium homeostasis; modulating intracellular calcium levels; modulating membrane polarization (membrane potential); modulating cation levels; and/or treating or preventing diseases, disorders, or conditions associated with calcium homeostasis, sodium homeostasis, calcium or sodium dyshomeostasis, or membrane polarization/hyperpolarization (including hypo and hyperexcitability), and/or treating or preventing diseases, disorders, or conditions associated with regulation or misregulation of TRPA1 expression or function. The present invention further relates to methods and compositions that antagonize both a function of TRPA1 and a function of one or more additional TRP channels.

  本发明涉及调节至少一个TRP家族成员的组合物和方法。具体而言，本发明涉及新型TRPA1拮抗剂及其在治疗疼痛（如慢性炎症性和神经病性疼痛）中的应用。能够调节一个或多个TRPA1功能的化合物在许多方面都很有用，包括但不限于维持钙离子平衡；维持钠离子平衡；调节细胞内钙离子水平；调节膜极化（膜电位）；调节阳离子水平；和/或治疗或预防与钙离子平衡、钠离子平衡、钙或钠离子失调或膜极化/去极化（包括低和高兴奋性）有关的疾病、障碍或病况，和/或治疗或预防与TRPA1表达或功能调节或失调有关的疾病、障碍或病况。本发明还涉及同时拮抗TRPA1的一个功能和一个或多个额外TRP通道的功能的方法和组合物。
• TRPA1 antagonists
  申请人：Bilodeau Mark T.

  公开号：US08829196B2

  公开（公告）日：2014-09-09

  The present invention relates to compositions and methods that modulate at least one TRP family member. Specifically, the present invention relates to novel TRPA1 antagonists and their use in the treatment of pain such as chronic inflammatory and neuropathic pain. Compounds that can modulate one or more TRPA1 functions are useful in many aspects including, but not limited to, maintaining calcium homeostasis; maintaining sodium homeostasis; modulating intracellular calcium levels; modulating membrane polarization (membrane potential); modulating cation levels; and/or treating or preventing diseases, disorders, or conditions associated with calcium homeostasis, sodium homeostasis, calcium or sodium dyshomeostasis, or membrane polarization/hyperpolarization (including hypo and hyperexcitability), and/or treating or preventing diseases, disorders, or conditions associated with regulation or misregulation of TRPA1 expression or function. The present invention further relates to methods and compositions that antagonize both a function of TRPA1 and a function of one or more additional TRP channels.

  本发明涉及调节至少一种TRP家族成员的组合物和方法。具体地，本发明涉及新型TRPA1拮抗剂及其在治疗疼痛（如慢性炎症性和神经病性疼痛）方面的应用。能够调节一个或多个TRPA1功能的化合物在许多方面都有用，包括但不限于维持钙离子稳态；维持钠离子稳态；调节细胞内钙离子水平；调节膜极化（膜电位）；调节阳离子水平；和/或治疗或预防与钙离子稳态、钠离子稳态、钙离子或钠离子失稳、膜极化/去极化（包括低和高兴奋性）或调节或调节失调TRPA1表达或功能相关的疾病、疾病或病情。本发明还涉及拮抗TRPA1功能和一个或多个额外TRP通道功能的方法和组合物。
• US8829196B2
  申请人：——

  公开号：US8829196B2

  公开（公告）日：2014-09-09
• [EN] NOVEL TRPA1 ANTAGONISTS<br/>[FR] NOUVEAUX ANTAGONISTES DE TRPA1
  申请人：MERCK SHARP & DOHME

  公开号：WO2011043954A1

  公开（公告）日：2011-04-14

  The present invention relates to compositions and methods that modulate at least one TRP family member. Specifically, the present invention relates to novel TRPA1 antagonists and their use in the treatment of pain such as chronic inflammatory and neuropathic pain. Compounds that can modulate one or more TRPA1 functions are useful in many aspects including, but not limited to, maintaining calcium homeostasis; maintaining sodium homeostasis; modulating intracellular calcium levels; modulating membrane polarization (membrane potential); modulating cation levels; and/or treating or preventing diseases, disorders, or conditions associated with calcium homeostasis, sodium homeostasis, calcium or sodium dyshomeostasis, or membrane polarization/hyperpolarization (including hypo and hyperexcitability), and/or treating or preventing diseases, disorders, or conditions associated with regulation or misregulation of TRPA1 expression or function. The present invention further relates to methods and compositions that antagonize both a function of TRPA1 and a function of one or more additional TRP channels.
• Sequential Ketyl−Olefin Coupling/β-Elimination Reactions Mediated by Samarium(II) Iodide
  作者：Gary A. Molander、Christina R. Harris

  DOI：10.1021/jo971889d

  日期：1998.2.1

  Samarium(II) iodide (SmI(2)) has been employed in an intramolecular sequential ketyl-olefin coupling/beta-elimination reaction. The overall process results in the net addition of an alkenyl species to a ketone carbonyl. This novel protocol for the intramolecular delivery of an alkenyl moiety avoids the basic reaction conditions typical of nucleophilic additions that are mediated by alkenylmagnesium

  碘化mar（II）（SmI（2））已用于分子内顺序的酮基-烯烃偶联/β消除反应。整个过程导致烯基物质净添加至酮羰基。该用于烯基部分的分子内递送的新颖方案避免了由烯基卤化镁和烯基锂试剂介导的亲核加成反应的典型基本反应条件。SmI（2）介导的过程中，由于最初的酮基-烯烃偶联反应具有出色的面部选择性，因此具有高度的立体控制能力。这些加成反应中引起的相对不对称诱导与更传统的亲核加成反应互补，因为烯基通过连接的系链被引导至羰基中心。