(RS)-4,7a-dimethyl-2,3,7,7a-tetrahydro-(6H)-indene-1,5-dione | 28255-09-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (RS)-4,7a-dimethyl-2,3,7,7a-tetrahydro-(6H)-indene-1,5-dione
• 英文别名: 2,6-dimethylbicyclo<4.3.0>non-1-en-3,7-dione；2,3,7,7a-tetrahydro-4,7a-dimethyl-1H-indene-1,5(6H)-dione；4,7a-dimethyl-2,3,7,7a-tetrahydro-1H-indene-1,5(6H)-dione；4,7a-dimethyl-2,3,7,7a-tetrahydro-6H-indene-1,5-dione；4,7a-Dimethyl-2,3,6,7-tetrahydroindene-1,5-dione；4,7a-dimethyl-7,7a-dihydro-1,5(6H)-indenedione
• CAS: 28255-09-6
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: NERGSGSEJNCZBN-UHFFFAOYSA-N

物化性质

• 沸点：
  310 ºC
• 密度：
  1.11
• 闪点：
  116 ºC

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2914190090

反应信息

• 作为反应物：
  描述：

  (RS)-4,7a-dimethyl-2,3,7,7a-tetrahydro-(6H)-indene-1,5-dione 在 吡啶 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 氯化亚砜 、 palladium on activated charcoal 、 氨 、 氢气 、 lithium 、 对甲苯磺酸 、 一水合肼 、 potassium hydroxide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 、 二乙二醇 为溶剂， 反应 99.5h， 生成 (±)-((3aS,7aS)-3a,7,7-trimethyloctahydro-1H-inden-2-yl)methanol
  参考文献：
  名称：

  [EN] OPSIN-BINDING LIGANDS, COMPOSITIONS AND METHODS OF USE
  [FR] LIGANDS DE LIAISON À UNE OPSINE, COMPOSITIONS ET PROCÉDÉS D'UTILISATION

  摘要：

  披露了一些化合物，可用于治疗由于或与在眼睛中积累的有毒视觉循环产物有关的眼科疾病，例如干性成人黄斑变性，以及由于或与突变视蛋白的错误折叠和/或视蛋白的错误定位有关的疾病。还描述了这些化合物单独或与其他治疗剂联合使用的组合物，以及使用这些化合物和/或组合物的治疗方法。还披露了合成这些药剂的方法。

  公开号：

  WO2013058809A1
• 作为产物：
  描述：

  2-methyl-2-(3-pentynyl)-1,3-cyclopentanedione 在 三氟化硼乙醚 、 水 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 (RS)-4,7a-dimethyl-2,3,7,7a-tetrahydro-(6H)-indene-1,5-dione
  参考文献：
  名称：

  Additive and Medium Effects on Lewis Acid-Promoted Cationic .pi.-Cyclizations of Alkenyl- and Alkynylcyclopentane-1,3-diones

  摘要：

  The effects of nucleophilic additives, Lewis and Bronsted acids, and solvents on BF3.Et(2)O-promoted cationic pi-cyclizations of alkynyl- and alkenylcyclopentane-1,3-diones are reported. The rates and selectivities of alkynyl dione cyclizations were significantly effected by the addition of external nucleophiles or water, and the regioselectivity of cyclization was effected by the choice of reaction solvent. Cyclizations of alkenyl diones, which fail under standard non-nucleophilic conditions, were found to be successful in the presence of added nucleophiles or with Lewis acids other than BF3.Et(2)O. The usefulness of these cationic pi-cyclizations for producing bicyclic ring systems of various functionality was also explored.

  DOI：

  10.1021/jo00107a012

文献信息

• Rearrangements of bicyclic-δ-hydroxy-α,β-enones—IV
  作者：S. Swaminathan、K.G. Srinivasan、P.S. Venkataramani

  DOI：10.1016/s0040-4020(01)92974-6

  日期：1970.1

  The hydroxy enones 5a, 5b, 5c, 4d, 4a and 4b rearrange when treated with aqueous alkali to the diones 6a, 6b, 8 and 13 and acids 9 and 12 respectively. The diones 2 and 6a are also formed by thermal rearrangement of enones 1a and 5a.

  当用碱水溶液处理时，羟基烯酮5a，5b，5c，4d，4a和4b重新排列成二酮6a，6b，8和13以及酸9和12。二酮2和6a也通过烯酮1a和5a的热重排而形成。
• Experiments in steroid synthesis: oestrone
  作者：D. J. Crispin、A. E. Vanstone、J. S. Whitehurst

  DOI：10.1039/j39700000010

  日期：——

  Some work leading to syntheses of oestrone is presented. It was generally found necessary to protect the 1-carbonyl function in 5,6,7,7a-tetrahydro-8β-methylindane-1,5-dione before the introduction of alkyl groups at position 4. Alkylations of 2-methylcyclopentane-1,3-dione have been made and the results compared with similar studies on 2-methylcyclohexane-1,3-dione.

  介绍了一些导致雌酮合成的工作。通常发现在引入4位烷基之前必须保护5,6,7,7a-四氢-8β-甲基茚满-1,5-二酮中的1-羰基官能团。2-甲基环戊烷-1的烷基化，制备了3-二酮，并将结果与​​2-甲基环己烷-1,3-二酮的类似研究进行了比较。
• Evaluating β-amino acids as enantioselective organocatalysts of the Hajos–Parrish–Eder–Sauer–Wiechert reaction
  作者：Stephen G. Davies、Angela J. Russell、Ruth L. Sheppard、Andrew D. Smith、James E. Thomson

  DOI：10.1039/b711171a

  日期：——

  A systematic study of the effect of substitution within the β-amino acid framework indicates that both β2- and β3-amino acids catalyse the Hajos–Parrish–Eder–Sauer–Wiechert reaction with poor to reasonable levels of enantioselectivity. These results led to the evaluation of the conformationally constrained β-amino acid (1R,2S)-cispentacin, which catalyses the Hajos–Parrish–Eder–Sauer–Wiechert reaction with comparable or higher levels of enantioselectivity to L-proline.

  对β-氨基酸框架内取代效应的系统研究表明，β2-和β3-氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性较低至合理。这些结果促使对构象受限的β-氨基酸(1R,2S)-cispentacin进行评估，该氨基酸催化Hajos–Parrish–Eder–Sauer–Wiechert反应的对映选择性与L-脯氨酸相比相当或更高。
• Chemoselective ethylene acetalization of α, β-unsaturated vis-à-vis saturated carbonyl groups
  作者：Theodore J. Nitz、Leo A. Paquette

  DOI：10.1016/0040-4039(84)80004-0

  日期：——

  The difficulties which in the past have precluded controlled acetalization of an α,β-unsaturated ketone functionality in the presence of a saturated carbonyl group can be overcome simply by making recourse to 2,4,6-collidinium p-toluenesulfonate as catalyst.

  过去难以通过在饱和羰基存在下控制α，β-不饱和酮官能团进行缩醛化的困难，可以简单地通过使用对甲苯磺酸2,4,6- collidinium对甲苯磺酸盐作为催化剂来克服。
• Efficient kinetic resolution of (±)-4-methyl-Hajos–Parrish ketone by baker’s yeast reduction
  作者：Hideaki Hioki、Takefumi Hashimoto、Mitsuaki Kodama

  DOI：10.1016/s0957-4166(00)00010-0

  日期：2000.2

  Kinetic resolution of (±)-4-methyl-Hajos–Parrish ketone (±)-2a using baker’s yeast reduction was investigated. The reaction rate and enantiomeric purity depended on the concentration of substrate and yeast. Under concentrated conditions, (−)-2a and the alcohol (+)-3 were obtained in high enantiomeric excess.

  （±）-4-甲基-豪约什-帕里什酮（±）动力学拆分-图2a使用面包酵母还原进行了研究。反应速率和对映体纯度取决于底物和酵母的浓度。在浓缩条件下，以高对映体过量获得（-）- 2a和醇（+）- 3。