3,5-二甲氧基-1-甲基环己-2,5-二烯-1-羧酸 | 64286-79-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 3,5-二甲氧基-1-甲基环己-2,5-二烯-1-羧酸
• 英文名称: 3,5-dimethoxy-1-methylcyclohexa-2,5-diene-1-carboxylic acid
• 英文别名: 3,5-dimethoxy-1-methylcyclohexa-2,5-dien-1-carboxylic acid；3-carboxy-3-methyl-1,5-dimethoxy-1,4-cyclohexadiene；1-methyl-3,5-dimethoxy-1,4-dihydrobenzoic acid；3,5-dimethoxy-1-methyl-2,5-cyclohexadiene-1-carboxylic acid；3,5-Dimethoxy-1-methylcyclohexa-2,5-dienecarboxylic acid
• CAS: 64286-79-9
• 化学式: C₁₀H₁₄O₄
• mdl: MFCD09910115
• 分子量: 198.219
• InChiKey: BNZOIACRCVTFKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  97-102 °C
• 沸点：
  367.9±42.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-二甲氧基-1-甲基环己-2,5-二烯-1-羧酸 在 盐酸 、 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 81.0h， 生成 5-甲基-5-(甲氧基甲基)-1,3-环己二酮
  参考文献：
  名称：

  Studies on terpenes. 8. Total synthesis of (.+-.)-linderalactone, (.+-.)-isolinderalactone, and (.+-.)-neolinderalactone, germacrane furanosesquiterpenes

  摘要：

  DOI：

  10.1021/jo00187a004
• 作为产物：
  描述：

  3,5-二甲氧基苯甲酸 、 碘甲烷 生成 3,5-二甲氧基-1-甲基环己-2,5-二烯-1-羧酸
  参考文献：
  名称：

  Synthesis of (.+-.)-linderalactone, (.+-.)-isolinderalactone, and (.+-.)-neolinderalactone

  摘要：

  DOI：

  10.1021/ja00525a064

文献信息

• 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。
• Organometallic compounds in organic synthesis. Part 13. Stereoselectivity of complexation of cyclohexadiene esters
  作者：B. M. Ratnayake Bandara、Arthur J. Birch、Warwick D. Raverty

  DOI：10.1039/p19820001755

  日期：——

  Complexation of cyclohexadienes with Fe(CO)3 as the entering group are subject to classical steric hindrance by alkyl groups, but CO2R and related groups introduce a competing factor because they favour sterically the entering group, probably through an intermediate complex. Increase of π-electron availability in the initial 1,4-diene by the attachment of OMe reduces this influence, probably because

  环己二烯与Fe（CO）3作为进入基团的络合会受到烷基的经典空间位阻，但是CO 2 R和相关基团引入了竞争因素，因为它们在空间上更倾向于进入基团，可能是通过中间配合物。通过OMe的连接增加初始1,4-二烯中π电子的利用率可减少这种影响，这可能是因为它有利于直接烯烃络合。非极性条件增加了CO 2的导向作用R，但是除非通过额外的烷基取代，否则无法实现完全的立体特异性。然而，许多立体异构体对可以分开，并且该路线导致许多空间确定的产物的前体，否则它们不易获得。
• Synthesis and activity of 5-(aminomethyl)-1,3-cyclohexanediones: enolic analogs of .gamma.-aminobutyric acid
  作者：Andre Mann、Christine Humblet、Jean Pierre Chambon、Remy Schlichter、Michel Desarmenien、Paul Feltz、Camille Georges Wermuth

  DOI：10.1021/jm00148a012

  日期：1985.10

  Eight 1,3-cyclohexanediones with an aminoalkyl side chain in the 5-position were synthesized as rigid enolic analogues of GABA (gamma-aminobutyric acid). Biochemical investigations about their abilities to displace [3H]GABA and [3H]baclofen [beta-(p-chlorophenyl)-gamma-aminobutyric acid] in binding studies or to inhibit the high-affinity sodium-dependent GABA uptake showed that these compounds were generally devoid of affinity for the two GABA receptors and for the GABA carrier. Only compound 1 exhibited a weak affinity in the GABA-A binding experiments (IC50 = 6.5 X 10(-5) M). Graphic computer modeling was applied in an attempt to explain this activity in comparison to some reference GABA agonists. Electrophysiological studies on dorsal root ganglia (DRG) also excluded agonistic or antagonistic properties on GABA-A or GABA-B receptor models but pointed out an atypical prolongation of Ca2+-dependent action potential for compound 1.
• Synthesis of (.+-.)-linderalactone, (.+-.)-isolinderalactone, and (.+-.)-neolinderalactone
  作者：Aravamudan Gopalan、Philip Magnus

  DOI：10.1021/ja00525a064

  日期：1980.2
• BANDARA, B. M. R.;BIRCH, A. J.;REVERTY, W. D., J. CHEM. SOC. PERKIN TRANS., 1982, N 8, 1755-1762
  作者：BANDARA, B. M. R.、BIRCH, A. J.、REVERTY, W. D.

  DOI：——

  日期：——