(1β,6β,7β)-1,7-Dimethylbicyclo<4.4.0>decane-2,8-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1β,6β,7β)-1,7-Dimethylbicyclo<4.4.0>decane-2,8-dione
• 英文别名: 5,9-Dimethyl-decalindion-1,6；(4aR,5R,8aS)-5,8a-dimethyl-3,4,4a,5,7,8-hexahydro-2H-naphthalene-1,6-dione
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: BAPYGQXRXLEUKO-LNLATYFQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5,8a-二甲基-3,4,8,8a-四氢-1,6-(2H,7H)-萘二酮 在 Pd/SrCO₃ 氢气 作用下， 生成 (1β,6β,7β)-1,7-Dimethylbicyclo<4.4.0>decane-2,8-dione
  参考文献：
  名称：

  Kucherov,V.F.; Gurvich,I.A., Journal of general chemistry of the USSR, 1961, vol. 31, p. 731 - 737

  摘要：

  DOI：

文献信息

• Metagenomic ene-reductases for the bioreduction of sterically challenging enones
  作者：Dragana Dobrijevic、Laure Benhamou、Abil E. Aliev、Daniel Méndez-Sánchez、Natalie Dawson、Damien Baud、Nadine Tappertzhofen、Thomas S. Moody、Christine A. Orengo、Helen C. Hailes、John M. Ward

  DOI：10.1039/c9ra06088j

  日期：——

  metagenomic approach was used to identify novel ERs from a drain metagenome. From the ten putative ER enzymes initially identified, eight exhibited activities towards widely accepted mono-cyclic substrates with several of the ERs giving high reaction yields and stereoselectivities. Two highly performing enzymes that displayed excellent co-solvent tolerance were used for the stereoselective reduction

  Old Yellow Enzyme 家族的烯还原酶 (ER) 催化活化烯烃的不对称还原，提供手性产物。它们已成为合成化学家工具箱中的一种重要方法，为金属催化的不对称还原提供了可持续的替代方案。然而，开发新的生物催化烯烃还原路线需要容易获得新的生物催化剂。使用基于序列的功能宏基因组方法从引流宏基因组中鉴定新的 ER。从最初鉴定的十种推定的 ER 酶中，八种表现出对广泛接受的单环底物的活性，其中几种 ER 具有高反应产率和立体选择性。两种表现出优异的共溶剂耐受性的高性能酶被用于立体选择性还原具有空间挑战性的双环烯酮，其中反应以高产率进行，这是迄今为止野生型 ER 前所未有的。在制备酶规模上，Hajos-Parish、Wieland-Miescher 衍生物和三环酮的还原以良好至优异的产率进行。
• Effect of C-9 Substituents on the Regioselectivity of A-Ring Reactions in Derivatives of the Wieland-Miescher Ketone
  作者：Kwangyong Park、William J. Scott、David F. Wiemer

  DOI：10.1021/jo00100a037

  日期：1994.10

  The nature of C-9 substituents Was found to have a significant influence on the regio- and stereochemistry of A-ring reactions in a variety of Wieland-Miescher ketone derivatives. For example, Pd-catalyzed hydrogenation of the C-9 dioxolanes resulted in much better selectivity for the cis-funded products vis-a-vis the corresponding C-9 ketone, with the parent Wieland-Miescher ketone itself and both C-4 methyl and C-4 carboalkoxy substituted analogues. In addition, methylation and acylation of A-ring enolates favored the C-2 isomer when a C-9 dioxolane group was present, but the C-4 substituted isomer was predominant with the corresponding C-9 ketone. These differences in regiochemistry may allow selective elaboration of cis-fused decalins during preparation of complex natural products.
• Park Kwangyong, Scott William J., Wiemer David F., J. Org. Chem, 59 (1994) N 21, S 6313-6317
  作者：Park Kwangyong, Scott William J., Wiemer David F.

  DOI：——

  日期：——
• Kucherov,V.F.; Gurvich,I.A., Journal of general chemistry of the USSR, 1961, vol. 31, p. 731 - 737
  作者：Kucherov,V.F.、Gurvich,I.A.

  DOI：——

  日期：——