(1R)-(-)-myrtenal | 185453-93-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1R)-(-)-myrtenal
• 英文别名: myrtanal；6,6-dimethylbicyclo[3.1.1]heptane-2-carbaldehyde；(1S,5S)-6,6-Dimethylbicyclo[3.1.1]heptane-2-carbaldehyde
• CAS: 185453-93-4
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: OOCLVMCVOWKECB-NPPUSCPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  [1R-(1alpha,2alpha,5alpha)]-6,6-二甲基螺[双环[3.1.1]庚烷-2,2'-环氧乙烷] 以72%的产率得到
  参考文献：
  名称：

  NOMURA, MASATO;FUJIHARA, YOSHIHITO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1988) N 3, 321-325

  摘要：

  DOI：

文献信息

• Anisole: a further step to sustainable hydroformylation
  作者：Fábio G. Delolo、Eduardo N. dos Santos、Elena V. Gusevskaya

  DOI：10.1039/c8gc03750g

  日期：——

  Hydroformylation, also known as the “oxo” process, is a major industrial process that employs rhodium or cobalt catalysts in solution; therefore the solvent of this process is a critical issue for its sustainability. Although several innovative solutions have been proposed recently, traditional fossil-derived solvents dominate the scenario for this reaction. In this paper, we studied a series of solvents

  加氢甲酰化，也称为“羰基合成”工艺，是一种在溶液中使用铑或钴催化剂的主要工业工艺。因此，该过程的溶剂性对其可持续性至关重要。尽管最近已经提出了几种创新的解决方案，但是传统的化石衍生溶剂主导了该反应的方案。在本文中，我们研究了在一系列烯烃的加氢甲酰化反应中，在最近的等级中被认为更具可持续性的一系列溶剂。苯甲醚是具有令人印象深刻的可持续性等级且很少在加氢甲酰化中使用的溶剂，被证明是该反应的绝佳替代品。
• Asymmetric Ene-Reduction of α,β-Unsaturated Compounds by F₄₂₀-Dependent Oxidoreductases A Enzymes from <i>Mycobacterium smegmatis</i>
  作者：Suk Woo Kang、James Antoney、Rebecca L. Frkic、David W. Lupton、Robert Speight、Colin Scott、Colin J. Jackson

  DOI：10.1021/acs.biochem.2c00557

  日期：2023.2.7

  The stereoselective reduction of alkenes conjugated to electron-withdrawing groups by ene-reductases has been extensively applied to the commercial preparation of fine chemicals. Although several different enzyme families are known to possess ene–reductase activity, the old yellow enzyme (OYE) family has been the most thoroughly investigated. Recently, it was shown that a subset of ene-reductases belonging to the flavin/deazaflavin oxidoreductase (FDOR) superfamily exhibit enantioselectivity that is generally complementary to that seen in the OYE family. These enzymes belong to one of several FDOR subgroups that use the unusual deazaflavin cofactor F420. Here, we explore several enzymes of the FDOR-A subgroup, characterizing their substrate range and enantioselectivity with 20 different compounds, identifying enzymes (MSMEG_2027 and MSMEG_2850) that could reduce a wide range of compounds stereoselectively. For example, MSMEG_2027 catalyzed the complete conversion of both isomers of citral to (R)-citronellal with 99% ee, while MSMEG_2850 catalyzed complete conversion of ketoisophorone to (S)-levodione with 99% ee. Protein crystallography combined with computational docking has allowed the observed stereoselectivity to be mechanistically rationalized for two enzymes. These findings add further support for the FDOR and OYE families of ene-reductases displaying general stereocomplementarity to each other and highlight their potential value in asymmetric ene-reduction.

  烯还原酶可立体选择性地还原烯与电子萃取基团的共轭，这种方法已被广泛应用于精细化学品的商业制备。尽管已知有多个不同的酶家族具有烯还原酶活性，但对老黄酶（OYE）家族的研究最为深入。最近的研究表明，属于黄素/去氮黄素氧化还原酶（FDOR）超家族的烯还原酶子集表现出的对映选择性通常与 OYE 家族的对映选择性互补。这些酶属于使用不常见的脱氮黄素辅助因子 F420 的几个 FDOR 亚群之一。在这里，我们研究了 FDOR-A 亚群的几种酶，用 20 种不同的化合物鉴定了它们的底物范围和对映体选择性，确定了可以立体选择性还原多种化合物的酶（MSMEG_2027 和 MSMEG_2850）。例如，MSMEG_2027 能催化柠檬醛的两种异构体完全转化为(R)-香茅醛，ee 为 99%；MSMEG_2850 能催化酮异佛尔酮完全转化为(S)-来伏二酮，ee 为 99%。蛋白质晶体学与计算对接相结合，使观察到的两种酶的立体选择性得到了机理上的合理解释。这些发现进一步支持了 FDOR 和 OYE 系列烯还原酶显示出一般的立体互补性，并突出了它们在不对称烯还原中的潜在价值。
• Biomass to value added chemicals: Isomerisation of β-pinene oxide over supported ionic liquid catalysts (SILCAs) containing Lewis acids
  作者：Eero Salminen、Luis Rujana、Päivi Mäki-Arvela、Pasi Virtanen、Tapio Salmi、Jyri-Pekka Mikkola

  DOI：10.1016/j.cattod.2014.05.024

  日期：2015.11

  The isomerisation of p-pinene oxide was studied over supported ionic liquid catalysts (SILCAs) consisting of Lewis acids in immobilized ionic liquid. SILCAs were demonstrated as efficient catalysts for the transformation of p-pinene oxide to myrtanal with the product distribution and activity being dependent on the nature of the ionic liquid and Lewis acid strength of catalytic species. With the catalyst ZnCl2/[N(3-OH-Pr)Py][NTf2]/ACC, the highest myrtanal molar yield obtained was 68%. (C) 2014 Elsevier B.V. All rights reserved.
• Masui, Masaichiro; Hosomi, Katsuko; Tsuchida, Keiichi, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 11, p. 4798 - 4802
  作者：Masui, Masaichiro、Hosomi, Katsuko、Tsuchida, Keiichi、Ozaki, Shigeko

  DOI：——

  日期：——
• NOMURA, MASATO;FUJIHARA, YOSHIHITO, J. CHEM. SOC. JAP., CHEM. AND IND. CHEM.,(1988) N 3, 321-325
  作者：NOMURA, MASATO、FUJIHARA, YOSHIHITO

  DOI：——

  日期：——