2,5-己二酮-D10 | 97135-07-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2,5-己二酮-D10
• 英文名称: <2H10>hexane-2,5-dione
• 英文别名: 2,5--Hexandion；1,1,1,3,3,4,4,6,6,6-decadeuterio-hexane-2,5-dione；2,5-Hexanedione-D10；1,1,1,3,3,4,4,6,6,6-decadeuteriohexane-2,5-dione
• CAS: 97135-07-4
• 化学式: C₆H₁₀O₂
• 分子量: 124.065
• InChiKey: OJVAMHKKJGICOG-MWUKXHIBSA-N

物化性质

• 溶解度：
  可溶于氯仿、乙酸乙酯（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2,5-己二酮-D10 在 sodium tetrahydroborate 作用下， 以 氯仿 为溶剂， 反应 72.0h， 生成 2,5-hexanediol-1,1,1,3,3,4,4,6,6,6-d10
  参考文献：
  名称：

  分子识别。15. 分子识别和立体选择性：二醇与多齿多羟基大环的多重氢键相互作用的几何要求

  摘要：

  间苯二酚-十二醛环四聚体 1 在 CDCl 3 中与环己二醇以及 2,4-戊烷和 2,5-己二醇作为其开链类似物以及环己醇和顺式和反式 4 形成氢键的 1/1 复合物-叔丁基环己醇。环状二醇对 1 的亲和力明显大于开链二醇和一元醇的亲和力。环己二醇的区域异构体和立体异构体取决于所涉及的两个 OH 基团的构型（轴向赤道 > 双赤道）和相对位置（1,4>>1,2>1,3），并以顺-1 的顺序递减,4>cis-1,2>trans-1,3>trans-1,4>cis-1,3>trans-1,2；因此立体选择性是cis-1,4/trans-1,4=8.0，cis-1,2/trans-1,2=2.5，和trans-1,3/cis-1,3=1.5。二醇结合的选择性根据二醇和 1 的多重氢键进行讨论

  DOI：

  10.1021/ja00004a042
• 作为产物：
  描述：

  2,5-己二酮 在 diclazuril 、 重水 作用下， 反应 48.0h， 生成 2,5-己二酮-D10
  参考文献：
  名称：

  分子识别。15. 分子识别和立体选择性：二醇与多齿多羟基大环的多重氢键相互作用的几何要求

  摘要：

  间苯二酚-十二醛环四聚体 1 在 CDCl 3 中与环己二醇以及 2,4-戊烷和 2,5-己二醇作为其开链类似物以及环己醇和顺式和反式 4 形成氢键的 1/1 复合物-叔丁基环己醇。环状二醇对 1 的亲和力明显大于开链二醇和一元醇的亲和力。环己二醇的区域异构体和立体异构体取决于所涉及的两个 OH 基团的构型（轴向赤道 > 双赤道）和相对位置（1,4>>1,2>1,3），并以顺-1 的顺序递减,4>cis-1,2>trans-1,3>trans-1,4>cis-1,3>trans-1,2；因此立体选择性是cis-1,4/trans-1,4=8.0，cis-1,2/trans-1,2=2.5，和trans-1,3/cis-1,3=1.5。二醇结合的选择性根据二醇和 1 的多重氢键进行讨论

  DOI：

  10.1021/ja00004a042

文献信息

• Di-tert-butyl hyponitrite as a source of alkoxyl radicals for dimerization
  作者：J. Protasiewicz、G. D. Mendenhall

  DOI：10.1021/jo00217a044

  日期：1985.8
• COMPOSITIONS AND RELATED METHODS FOR AGRICULTURE
  申请人：Flagship Pioneering Innovations V, Inc.

  公开号：US20210289794A1

  公开（公告）日：2021-09-23

  The invention comprises methods for decreasing colonization by a bacterium of a gut of a stink bug, the method comprising providing a composition comprising vanillin or an analog thereof; and delivering said composition to an egg from which the stink bug will hatch, whereby colonization by the bacterium within the gut of the stink bug hatched from the egg treated with the composition is decreased relative to a stink bug hatched from an untreated egg. In some embodiments, the decrease in colonization by the bacterium decreases the fitness of the stink bug, e.g., decreases reproductive ability, survival, rate of development, number of eggs, number of hatched eggs, adult emergence rate, body length, body width, body mass, or cuticle thickness. In some embodiments of the methods herein, the bacterial colonization-disrupting agent is an inhibitor of bacterial metabolism. In some embodiments, the bacterial colonization-disrupting agent is a polyhydroxyalkanoate (PHA) synthesis inhibitor.
• Molecular recognition. 15. Molecular recognition and stereoselectivity: geometrical requirements for the multiple hydrogen-bonding interaction of diols with a multidentate polyhydroxy macrocycle
  作者：Yasuaki Kikuchi、Yasushi Kato、Yasutaka Tanaka、Hiroo Toi、Yasuhiro Aoyama

  DOI：10.1021/ja00004a042

  日期：1991.2

  Resorsinol-dodecanal cyclotetramer 1 in CDCl 3 forms hydrogen-bonded, 1/1 complexes with cyclohexanediols as well as with 2,4-pentane- and 2,5-hexanediol as their open-chain analogues and cyclohexanol and cis- and trans-4-tert-butylcyclohexanol. The affinities to 1 of cyclic diols are significantly larger than those of open-chain diols and monools. Those of regio- and stereoisomers of cyclohexanediol

  间苯二酚-十二醛环四聚体 1 在 CDCl 3 中与环己二醇以及 2,4-戊烷和 2,5-己二醇作为其开链类似物以及环己醇和顺式和反式 4 形成氢键的 1/1 复合物-叔丁基环己醇。环状二醇对 1 的亲和力明显大于开链二醇和一元醇的亲和力。环己二醇的区域异构体和立体异构体取决于所涉及的两个 OH 基团的构型（轴向赤道 > 双赤道）和相对位置（1,4>>1,2>1,3），并以顺-1 的顺序递减,4>cis-1,2>trans-1,3>trans-1,4>cis-1,3>trans-1,2；因此立体选择性是cis-1,4/trans-1,4=8.0，cis-1,2/trans-1,2=2.5，和trans-1,3/cis-1,3=1.5。二醇结合的选择性根据二醇和 1 的多重氢键进行讨论
• Intermediates in the Paal-Knorr synthesis of pyrroles
  作者：Venkataraman Amarnath、Douglas C. Anthony、Kalyani Amarnath、William M. Valentine、Lawrence A. Wetterau、Doyle G. Graham

  DOI：10.1021/jo00024a040

  日期：1991.11

  The mechanism of Paal-Knorr reaction between a 1,4-dicarbonyl compound and ammonia or a primary amine to form a pyrrole is explored. In aprotic solvents and in aqueous solutions near neutrality, d,l diastereomers of 3,4-dimethyl- and 3,4-diethyl-2,5-hexanediones (1r and 2r) formed pyrroles 1.3-57.0 times faster than the corresponding meso diastereomers (1m and 2m). This contradicts any intermediate, such as the enamine 15, which does not remain saturated at both the 3- and 4-positions through the rate-determining step. The demonstrated stereoisomeric difference in reactivity coupled with the following results support the hemiaminal (9) as the intermediate undergoing cyclization in the rate-limiting step of the Paal-Knorr reaction: (1) The reaction rate was adversely affected by increase in the size of the alkyl substituents on the dione. (2) Racemic 2,3-dimethyl-1,4-diphenyl-1,4-butanedione (3r) was more reactive toward ammonium acetate (2.2:1) and 2-aminoethanol (11.2:1) than the meso isomer (3m), ruling out the involvement of the less substituted enamine 14. (3) The relative rate of pyrrole formation of 1,4-diphenyl-1,4-butanedione (5) and its dimethoxy (6) and dinitro (7) derivatives (1:03:6) does not support cyclization of the imine (11) to the pyrrolinium ion (12). (4) The rates of reaction of 2,2,3,3-tetradeuterio-1,4-diphenyl-1,4-butanedione (5D) and perdeuterio-2,5-hexanedione (4D) were very close to those of unlabeled diketones, indicating the absence of a primary isotope effect in the reaction. (5) Neither the isomerization of the unreacted diastereomers of 1, 2, and 3 nor hydrogen exchange of 4D and 5D was detected during the reaction.