5,5-dimethyl-2-oxocyclohexane-1-carbaldehyde | 77630-11-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,5-dimethyl-2-oxocyclohexane-1-carbaldehyde
• 英文别名: 5,5-dimethyl-2-oxocyclohexanecarbaldehyde；5,5-dimethyl-2-oxo-cyclohexanecarbaldehyde
• CAS: 77630-11-6
• 化学式: C₉H₁₄O₂
• 分子量: 154.209
• InChiKey: NLQPHBAIRKKSBI-UHFFFAOYSA-N

物化性质

• 沸点：
  232.4±33.0 °C(Predicted)
• 密度：
  1.042±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,5-dimethyl-2-oxocyclohexane-1-carbaldehyde 在 N-碘代丁二酰亚胺 、 草酰氯 、 乙醇 、 水 、 sodium 、 溶剂黄146 、 lithium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 氯仿 为溶剂， 反应 26.25h， 生成 3-iodo-5,5-dimethyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylic acid
  参考文献：
  名称：

  Novel S1P₁ Receptor Agonists - Part 2: From Bicyclo[3.1.0]hexane-Fused Thiophenes to Isobutyl Substituted Thiophenes

  摘要：

  Previously, we reported on the discovery of a novel series of bicyclo[3.1.0]hexane fused thiophene derivatives that serve as potent and selective S1P(1), receptor agonists. Here, we discuss our efforts to simplify the bicyclohexane fused thiophene head. In a first step the bicyclohexane moiety could be replaced by a simpler, less rigid cyclohexane ring without compromising the SIP receptor affinity profile of these novel compounds. In a second step, the thiophene head was simplified even further by replacing the cyclohexane ring with an isobutyl group attached either to position 4 or position S of the thiophene. These structurally much simpler headgroups again furnished potent and selective S1P(1) agonists (e.g., 87), which efficiently and dose dependently reduced the number of circulating lymphocytes upon oral administration to male Wistar rats. For several compounds discussed in this report lymphatic transport is an important route of absorption that may offer opportunities for a tissue targeted approach with minimal plasma exposure.

  DOI：

  10.1021/jm401456d
• 作为产物：
  描述：

  4,4-二甲基-2-环己基-1-酮 在 palladium on activated charcoal 氢气 、 sodium hydride 作用下， 以 环己烷 、 正戊烷 为溶剂， 反应 28.0h， 生成 5,5-dimethyl-2-oxocyclohexane-1-carbaldehyde
  参考文献：
  名称：

  新型 19-Nor-Steroids 的双 Heck 反应立体选择性合成

  摘要：

  雌二醇 4 是通过两个连续的 Heck 反应合成的，从对映纯 2 和环己烯酮 5 开始，环己烯酮 5 含有 (Z)-溴乙烯基。第一个分子间 Pd 催化的反应以高度区域和非对映选择性的方式产生 10。将烯酮 10 转化为相应的烯醇三氟甲磺酸酯 14，然后进行分子内 Heck 反应，以高产率提供具有环 B 和 C 的不寻常顺式连接的环化产物 4。

  DOI：

  10.1002/1099-0690(200105)2001:9<1619::aid-ejoc1619>3.0.co;2-t

文献信息

• Highly Selective Hydrogenation of C═C Bonds Catalyzed by a Rhodium Hydride
  作者：Yiting Gu、Jack R. Norton、Farbod Salahi、Vladislav G. Lisnyak、Zhiyao Zhou、Scott A. Snyder

  DOI：10.1021/jacs.1c04683

  日期：2021.6.30

  Under mild conditions (room temperature, 80 psi of H2) Cp*Rh(2-(2-pyridyl)phenyl)H catalyzes the selective hydrogenation of the C═C bond in α,β-unsaturated carbonyl compounds, including natural product precursors with bulky substituents in the β position and substrates possessing an array of additional functional groups. It also catalyzes the hydrogenation of many isolated double bonds. Mechanistic

  在温和条件下（室温，80 psi H 2）Cp*Rh(2-(2-吡啶基)苯基)H催化α,β-不饱和羰基化合物（包括天然产物前体）中C=C键的选择性氢化在 β 位具有庞大的取代基，并且底物具有一系列额外的官能团。它还催化许多分离的双键的氢化。机理研究表明，不涉及自由基中间体，并且催化剂似乎是均相的，从而为类似氢化过程的现有方案提供了重要的互补性。
• Hydrogenated Benzo (C) Thiophene Derivatives as Immunomodulators
  申请人：Bolli Martin

  公开号：US20080176926A1

  公开（公告）日：2008-07-24

  The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

  该发明涉及新型噻吩衍生物，其制备以及其作为药用活性化合物的用途。这些化合物特别作为免疫抑制剂。
• Novel Pyridine Derivatives
  申请人：Bolli Martin

  公开号：US20090005421A1

  公开（公告）日：2009-01-01

  The invention relates to novel pyridine derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

  这项发明涉及新型吡啶衍生物，它们的制备以及它们作为药用活性化合物的用途。这些化合物特别作为免疫抑制剂。
• Novel Thiophene Derivatives
  申请人：Bolli Martin

  公开号：US20080300294A1

  公开（公告）日：2008-12-04

  The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

  本发明涉及新型噻吩衍生物，其制备和用作药物活性化合物。所述化合物特别作为免疫抑制剂。
• HYDROGENATED BENZO (C) THIOPHENE DERIVATIVES AS IMMUNOMODULATORS
  申请人：Bolli Martin

  公开号：US20100204198A1

  公开（公告）日：2010-08-12

  The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

  该发明涉及新型噻吩衍生物，其制备及其作为药物活性化合物的用途。所述化合物特别作为免疫抑制剂。