5-戊基环己烷-1,3-二酮 | 18456-88-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-戊基环己烷-1,3-二酮
• 英文名称: 5-Pentyl-1,3-cyclohexanedione
• 英文别名: 5-Pentylcyclohexane-1,3-dione
• CAS: 18456-88-7
• 化学式: C₁₁H₁₈O₂
• mdl: MFCD03844395
• 分子量: 182.263
• InChiKey: DBEXKDYDVZVANM-UHFFFAOYSA-N

物化性质

• 熔点：
  70-71 °C
• 沸点：
  298.9±23.0 °C(Predicted)
• 密度：
  0.977±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.818
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914299000

反应信息

• 作为反应物：
  描述：

  5-戊基环己烷-1,3-二酮 在 吡啶 、 三氯化铝 作用下， 以 氯仿 、 1,2-二氯乙烷 为溶剂， 反应 3.0h， 生成 2-acetyl-5-pentyl-1,3-cyclohexanedione
  参考文献：
  名称：

  Synthesis and anticonvulsant and sedative-hypnotic activity of 4-(alkylimino)-2,3-dihydro-4H-1-benzopyrans and benzothiopyrans

  摘要：

  A series of 4-(alkylimino)-5-hydroxy-7-alkyl-2,3-dihydro-4H-1-benzopyrans and -thiopyrans were synthesized and evaluated for anticonvulsant activity. Preliminary screening of these compounds revealed that 2,2-dimethyl-4-[(2-hydroxyalkyl)imino]-5-hydroxy-7-pentyl-2,3- dihydro-4H-1-benzopyrans 19 and 29, the 7-butyl analogue 34, and the corresponding 7-pentyl-4H-1-benzothiopyrans 38 and 39 had the most promising anticonvulsant activity. Synthesis of both enantiomers of 29 and 39 indicated that the R isomers 30 and 40 were the most active and showed very good protection against MES, pentylenetetrazole, and mercaptopropionic acid induced seizures after oral administration in mice. In the Irwin test these compounds showed a generalized depressant activity but at dosages higher than those showing anticonvulsant activity, whereas acute toxicity after oral administration was low (LD50 higher than 400 mg/kg).

  DOI：

  10.1021/jm00172a030
• 作为产物：
  描述：

  3,5-二羟基戊苯 在 sodium hydroxide 、 镍 作用下， 125.0 ℃ 、18.63 MPa 条件下， 生成 5-戊基环己烷-1,3-二酮
  参考文献：
  名称：

  Structure of Cannabinol. I. Preparation of an Isomer, 3-Hydroxy-1-n-amyl-6,6,9-trimethyl-6-dibenzopyran

  摘要：

  DOI：

  10.1021/ja01865a081

文献信息

• Thermal Isomerization of Cannabinoid Analogues
  作者：Angie Garcia、Dan Borchardt、Chia-En A. Chang、Michael J. Marsella

  DOI：10.1021/ja907062v

  日期：2009.11.25

  Thermal isomerization of CBC(an) to THC(an) [nonaromatic analogues of plant cannabinoids cannabichromene (CBC) and Delta(1)-tetrahydrocannabinol (THC), respectively] is predicted in silico and demonstrated experimentally. Density functional theory calculations support a similar isomerization mechanism for the corresponding plant cannabinoids. Docking studies suggest that THC(an), although nonaromatic

  CBC(an) 热异构化为 THC(an) [植物大麻素大麻素 (CBC) 和 Delta(1)-四氢大麻酚 (THC) 的非芳香类似物，分别] 是在计算机中预测的，并通过实验进行了证明。密度泛函理论计算支持相应植物大麻素的类似异构化机制。对接研究表明 THC(an) 虽然非芳香族，但具有与天然 THC 相似的 CB(1) 受体结合亲和力。
• Synthesis of chiloglottones – semiochemicals from sexually deceptive orchids and their pollinators
  作者：Jacqueline Poldy、Rod Peakall、Russell Allan Barrow

  DOI：10.1039/b912233h

  日期：——

  a 3-alkyl resorcinol derivative (3) precedes alkylation was applied in the synthesis of chiloglottone 1 (1dc), in 58% overall yield. Chiloglottone 1 is a member of a new class of natural products, representing a known sex pheromone of the thynnine wasp Neozeleboria cryptoides and pollinator attractant in the Australian sexually deceptive orchid genus Chiloglottis. The synthetic homologues were assessed

  通过一个顺序描述了单烷基和2,5-二烷基-1,3-环己二酮（1）的五步合成过程，该过程涉及从容易获得且廉价的起始原料进行连续的桦木还原和烷基化，3,5-二甲氧基苯甲酸。考虑了两种方法，其中在C-2处的烷基化发生在所提出的还原之前或之后。一种成功的方法，其中3-烷基间苯二酚衍生物（3）的桦木还原在烷基化之前进行，已成功用于合成Chiloglottone 1（1dc），总收率为58％。Chiloglottone 1是一类新的天然产物的成员，代表了澳大利亚性欺骗性兰花属Chiloglottis中的一种已知的胸腺黄蜂新性紫斑狼疮性信息素和传粉媒介引诱剂。通过电造影检查评估合成的同系物的生物活性。
• Unifying Metal- and Organocatalysis for Asymmetric Oxidative Iminium Activation: A Relay Catalytic System Enabling the Combined Allylic Oxidation of Alcohols and Prolinol Ether Catalyzed Iminium Reactions
  作者：Magnus Rueping、Henrik Sundén、Erli Sugiono

  DOI：10.1002/chem.201102551

  日期：2012.3.19

  A multicatalytic system consisting of tetrapropylammonium perruthenate/N‐methylmorpholine N‐oxide (TPAP/NMO) as oxidant, and diarylprolinol TMS‐ether as chiral amine catalyst, has been developed and applied in the efficient construction of valuable chiral molecules. The one‐pot domino reactions elaborated in the present study are based on the in situ generation of α,β‐unsaturated aldehydes from allylic

  由四丙基过钌酸铵/ N-甲基吗啉N组成的多催化体系-氧化物（TPAP / NMO）作为氧化剂，二芳基脯氨醇TMS-醚作为手性胺催化剂，已被开发并应用于有效构建有价值的手性分子。本研究中阐述的单锅多米诺骨牌反应是基于从烯丙醇原位生成 α,β-不饱和醛及其随后用于各种不对称转化（例如，环丙烷化、迈克尔加成、迈克尔加成/缩醛化）。TPAP 作为底物选择性氧化还原催化剂，对胺催化剂具有良好的耐受性，并且多米诺反应以良好的收率和高对映选择性进行。本文提出的金属和有机催化的相容性拓宽了不对称亚胺催化的范围。
• High-Yielding Total Synthesis of Sexually Deceptive Chiloglottones and Antimicrobial Dialkylresorcinols through an Organocatalytic Reductive Coupling Reaction
  作者：Rudrakshula Madhavachary、Dhevalapally B. Ramachary

  DOI：10.1002/ejoc.201403128

  日期：2014.11

  Biologically important, less-explored natural products of sexually deceptive chiloglottones, antimicrobial dialkylresorcinols, and their many analogues were synthesized in very good yields in a sequential two-pot manner by using an “organocatalytic reductive coupling reaction” as the key step.

  通过使用“有机催化还原偶联反应”作为关键步骤，以连续两锅的方式以非常好的收率合成了具有生物学意义的、较少探索的具有性欺骗性的 chiloglottones、抗菌二烷基间苯二酚及其许多类似物的天然产物。
• Enantio- and Diastereoselective Access to Distant Stereocenters Embedded within Tetrahydroxanthenes: Utilizing<i>ortho</i>-Quinone Methides as Reactive Intermediates in Asymmetric Brønsted Acid Catalysis
  作者：Chien-Chi Hsiao、Hsuan-Hung Liao、Magnus Rueping

  DOI：10.1002/anie.201406587

  日期：2014.11.24

  tetrahydroxanthenones by means of asymmetric Brønsted acid catalysis has been developed. A chiral binol‐based N‐triflyphosphoramide was found to promote the in situ generation of ortho‐quinone methides and their subsequent reaction with 1,3‐cyclohexanedione to provide the desired products with excellent enantioselectivities. In addition, a highly enantio‐ and diastereoselective Brønsted acid catalyzed desymmetrization

  已经开发了通过不对称布朗斯台德酸催化方法高度对映选择性合成9-取代的四氢黄酮酮的方案。发现基于手性二元醇的N-三氟磷酰胺可促进原醌甲基化物的原位生成及其随后与1,3-环己二酮的反应，从而提供具有优异对映选择性的所需产物。此外，高对映体和非对映体选择性布朗斯台德酸催化5单取代的1,3-二羰基底物与邻醌甲基化的不对称反应产生了有价值的含有两个遥远立构中心的四氢氧杂蒽。