(1R)-myrtenal | 923014-44-2

• 分子结构分类: 有机化合物 - 有机氧化合物 - 有机氧化物
• 英文名称: (1R)-myrtenal
• 英文别名: (1S,5R)-isomyrtenal；(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-ene-3-carbaldehyde；Isomyrtenal
• CAS: 923014-44-2
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: LXYRFKMCSIWPAZ-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 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)-myrtenal 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 110.5h， 生成 1-(3'-chlorobiphenyl-4-yl)-N-(((1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl)methyl)-N,N-dimethylmethanaminium iodide
  参考文献：
  名称：

  Chemical Subtleties in Small-Molecule Modulation of Peptide Receptor Function: The Case of CXCR3 Biaryl-Type Ligands

  摘要：

  The G protein-coupled chemokine receptor CXCR3 plays a role in numerous inflammatory events. The endogenous ligands for the chemokine receptors are peptides, but in this study we disclose small-molecule ligands that are able to activate CXCR3. A class of biaryl-type compounds that is assembled by convenient synthetic routes is described as a new class of CXCR3 agonists. Intriguingly, structure-activity relationship and structure-function relationship studies reveal that subtle chemical modifications on the outer aryl ring (e.g., either the size or position of a halogen atom) result in a full spectrum of agonist efficacies on CXCR3. Quantum mechanics calculations and nuclear Overhauser effect spectroscopy NMR studies suggest that the biaryl dihedral angle and the electronic nature of ortho-substituents play an important role in determining agonist efficacies. Compounds 38 (VUF11222) and 39 (VUF11418) are the first reported nonpeptidomimetic agonists on CXCR3, rendering them highly useful chemical tools for detailed assessment of CXCR3 activation as well as for studying downstream CXCR3 signaling.

  DOI：

  10.1021/jm301240t
• 作为产物：
  描述：

  [(1S,5R)-6,6-dimethylbicyclo[3.1.1]hept-2-en-3-yl]methanol 在 palladium diacetate potassium phosphate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以82%的产率得到(1R)-myrtenal
  参考文献：
  名称：

  α-溴亚砜作为助氧化剂的厌氧钯催化烯丙醇和苯甲醇的化学选择性氧化

  摘要：

  首次描述了使用α-溴亚砜作为助氧化剂的化学选择性钯催化的烯丙醇和苄醇的厌氧氧化。由于在非需氧条件下膦配体的存在，该催化剂体系简单且寿命长。所描述的方法的优点包括：由于所施加的温和条件而不会使伯醇过度氧化为羧酸；对氧敏感的官能团如碳-碳双键，有机硫基或二有机氨基的耐受性以及有效的制备方法由伯和仲烯丙基醇的氧化产生的α，β-不饱和醛和酮的分解，因为不会发生与助氧化剂的竞争性Heck反应。

  DOI：

  10.1002/adsc.200600394

文献信息

• Controlling the Helicity of 2,2‘-Bipyridyl Ruthenium(II) and Zinc(II) Hemicage Complexes
  作者：Karl D. Oyler、Frederick J. Coughlin、Stefan Bernhard

  DOI：10.1021/ja067016v

  日期：2007.1.1

  Complexation of these ligands to Ru(II) afforded diastereomerically pure Delta and Lambda isomers, as verified through circular dichroism and circularly polarized luminescence spectroscopy. Ligands (+)-L2 and (-)-L2 were further coordinated to Zn(II) to form a complex with intriguing photophysical properties. Whereas Zn(bpy)32+ was shown to be a fluorescent emitter outside the visible spectrum, the

  合成了新的 4,5-pineno-2,2'-bipyridine 配体的两种对映异构体，随后通过苯基接头将配体掺入 hemicage 配体中以产生配体 (+)-L1 和 (-)-L1 或通过 mesityl 接头产生配体 (+)-L2 和 (-)-L2。这些配体与 Ru(II) 的络合提供了非对映异构纯的 Delta 和 Lambda 异构体，通过圆二色性和圆偏振发光光谱证实。配体 (+)-L2 和 (-)-L2 进一步与 Zn(II) 配位以形成具有有趣光物理特性的复合物。虽然 Zn(bpy)32+ 被证明是可见光谱之外的荧光发射体，但笼罩过程提供了前所未有的系统间交叉增强，随后切换到蓝光的磷光发射。此外，
• In situ Catalytic Generation of Allylcopper Species for Asymmetric Allylation: Toward 1<i>H</i>-Isochromene Skeletons
  作者：Junya Kawai、Prasanna Kumara Chikkade、Yohei Shimizu、Motomu Kanai

  DOI：10.1002/anie.201302027

  日期：2013.7.8

  Stay active: Allylcopper species can be generated in situ through catalytic intramolecular oxycupration of allenic alcohol. The allylcopper can react with various aldehydes and a ketone to give 1H‐isochromene derivatives in an enantioselective manner (see scheme; HMPA=hexamethylphosphoramide, THF=tetrahydrofuran). The protocol is atom‐economical, highly regioselective, stereoconvergent, and tolerant

  保持活性：烯丙醇的催化分子内氧合可以原位生成烯丙基铜。烯丙基铜可以与多种醛和酮反应，以对映选择性的方式生成1 H-异戊二烯衍生物（参见方案； HMPA =六甲基磷酰胺，THF =四氢呋喃）。该方案是原子经济的，高度区域选择性的，立体会聚的，并且对游离羟基具有耐受性。
• Triple-Consecutive Isocyanide Insertions with Aldehydes: Synthesis of 4-Cyanooxazoles
  作者：Shaohang Lu、Chang-Hua Ding、Bin Xu

  DOI：10.1021/acs.orglett.3c00008

  日期：2023.2.10

  An efficient TMSOTf-promoted selective triple consecutive insertions of tert-butyl isocyanide into aldehydes has been developed, affording pharmacological interesting 4-cyanooxazoles in high yields in a one pot manner. The given method encompasses a wide range of substrates with tert-butyl isocyanide serving as sources of critical “CN” and “C–N═C” moieties. The versatile transformations of the resulting

  已经开发出一种有效的 TMSOTf 促进的选择性三次连续插入异氰化叔丁基到醛中，以一锅法以高产率提供药理学上有趣的 4-氰基恶唑。给定的方法涵盖了广泛的底物，其中叔丁基异氰化物作为关键“CN”和“C-N=C”部分的来源。证明了所得 4-氰基恶唑的多种转化。确定了可能机制的关键反应中间体。
• PmHNL catalyzed synthesis of (R)-cyanohydrins derived from aliphatic aldehydes
  作者：Samik Nanda、Yasuo Kato、Yasuhisa Asano

  DOI：10.1016/j.tetasy.2006.02.003

  日期：2006.3

  Hydroxynitrile lyase from the Japanese apricot (Prunus mume) catalyzes the formation of several aliphatic cyanohydrins in an asymmetric fashion. By employing a biphasic reaction system, aliphatic aldehydes with various structural features can be converted to the corresponding (R)-cyanohydrins with good overall yield and enantiomeric excess. (c) 2006 Elsevier Ltd. All rights reserved.
• The biocatalyzed stereoselective preparation of polycyclic cyanohydrins
  作者：M.Manuel Cruz Silva、M.Luisa Sá e Melo、Marco Parolin、Davide Tessaro、Sergio Riva、Bruno Danieli

  DOI：10.1016/j.tetasy.2003.11.003

  日期：2004.1

  The enzyme-mediated preparation of enantiomerically or diastereomerically enriched polycyclic cyanohydrins has been investigated. Oxynitrilase-catalyzed cyanurations gave excellent results with the bicyclic aldehydes tested. On the other hand, enantio- or diastereoselective acylation, catalyzed by lipase PS or subtilisin, proved to be a more versatile methodology, giving good results even with sterically hindered polycyclic cyanohydrins. Specifically, the steroidal cyanohydrin derivative 4b was isolated with a 89% de. (C) 2003 Elsevier Ltd. All rights reserved.