2-(1,4-dioxaspiro[4.5]dec-6-yl)ethanol | 57133-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(1,4-dioxaspiro[4.5]dec-6-yl)ethanol
• 英文别名: 2-(1,4-dioxaspiro[4.5]decan-6-yl)ethan-1-ol；2-(1,4-Dioxa-spiro[4.5]dec-6-yl)-aethanol；(+/-)-6-(2'-hydroxyethyl)-1,4-dioxaspiro[4.5]decane；2-{1,4-Dioxaspiro[4.5]decan-6-yl}ethan-1-ol；2-(1,4-dioxaspiro[4.5]decan-6-yl)ethanol
• CAS: 57133-56-9
• 化学式: C₁₀H₁₈O₃
• mdl: MFCD25964778
• 分子量: 186.251
• InChiKey: RQUYFWFESBKKAW-UHFFFAOYSA-N

物化性质

• 沸点：
  148-150 °C(Press: 13 Torr)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1,4-dioxaspiro[4.5]dec-6-yl)ethanol 在 盐酸 、 sodium tetrahydroborate 、 草酰氯 、 异丙基氯化镁 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 7.0h， 生成 15,16-dimethoxy-cis-erythrinane
  参考文献：
  名称：

  An Improved Stereocontrolled Route to cis-Erythrinanes by Combined Intramolecular Strecker and Bruylants Reaction

  摘要：

  Condensation of (2-iodophenyl)ethylamines with cyclohexanoylacetaldehyde provided the corresponding aldimines which were reduced yielding secondary phenethylcyclohexanoylethylamines. These in turn were appropriate intermediates to prepare several erythrinanes by a sequential intramolecular Strecker and intramolecular Bruylants reaction. In contrast, the C-ring homologue schelhammeranes were not available on this route.

  DOI：

  10.1007/s00706-004-0184-8
• 作为产物：
  描述：

  2-环己酮乙酸乙酯 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 7.0h， 生成 2-(1,4-dioxaspiro[4.5]dec-6-yl)ethanol
  参考文献：
  名称：

  The synthesis of (R)-(+)-lipoic acid using a monooxygenase-catalysed biotransformation as the key step

  摘要：

  2-(2-Acetoxyethyl)cyclohexanone (4) was converted into the lactone (-)-(5) regio- and enantioselectively using 2-oxo-Delta(3)-4,5,5-trimethylcyclopentenyl acetyl-CoA monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from camphor grown Pseudomonas putida NCIMB 10007. The lactone (-)-(5) was converted into (R)-(+)-lipoic acid in six steps. In contrast cyclopentanone monooxygenase, an NADPH-dependent Baeyer-Villiger monooxygenase from cyclopentanol-grown Pseudomonas sp. NCIMB 9872 selectively oxidized the (S)-enantiomer of the ketone (4) giving better access to optically enriched, naturally occurring lipoic acid. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(96)00234-9

文献信息

• N-dihydroxyalkyl-substituted 2-oxo-imidazole derivatives
  申请人：Hashimoto Masaya

  公开号：US20070015792A1

  公开（公告）日：2007-01-18

  The invention provides the compounds represented by the formula (I) in which, R stands for a dihydroxy-substituted C 1 -C 6 alkyl group, and Cy stands for an optionally substituted C 6 -C 10 bi- or tri-cyclic aliphatic carbocyclic group. These compounds act as nociceptin receptor antagonist, and are useful, for example, as relievers against tolerance to narcotic analgesic, dependence on narcotic analgesic or addiction; analgesic enhancers; antiobestic or appetite suppressors; treating or prophylactic agents for cognitive impairment and dementia/amnesia; agents for treating developmental cognitive abnormality; remedy for schizophrenia; agents for treating neurodegenerative diseases; anti-depressant or treating agents for affective disorder; treating or prophylactic agents for diabetes insipidus; treating or prophylactic agents for polyuria; and remedy for hypotension and the like.

  该发明提供了由式(I)表示的化合物，其中R代表二羟基取代的C1-C6烷基基团，Cy代表一个可选择取代的C6-C10双环或三环脂肪环碳环基团。这些化合物作为痛觉受体拮抗剂，例如，可用作缓解对麻醉镇痛药的耐受性、对麻醉镇痛药的依赖或成瘾的药物；镇痛增强剂；抗肥胖或食欲抑制剂；治疗或预防认知障碍和失忆症/健忘症的药物；治疗发育性认知异常的药物；治疗精神分裂症的药物；治疗神经退行性疾病的药物；抗抑郁或治疗情感障碍的药物；治疗或预防尿崩症的药物；治疗或预防多尿症的药物；以及治疗低血压等的药物。
• Process for the production of lipoic acid
  申请人：ASTA Medica Aktiengesellschaft

  公开号：US06140512A1

  公开（公告）日：2000-10-31

  A process for the preparation of lipolic acid (thioctic acid), or a derivative thereof, is one in which a 2-substituted cyclohexanone is transformed in an oxidation reaction to a lactone having formula (I), wherein X is a heteroatom substituent.

  一种制备脂肪酸（硫辛酸）或其衍生物的方法是将2-取代环己酮在氧化反应中转化为具有化学式（I）的内酯，其中X是一个杂原子取代基。
• Photolysis of α-diazocyclopentanones. Ring contraction to functionalised cyclobutanes and synthesis of junionone, grandisol and planococcyl acetate
  作者：Arun Ghosh、Ujjal K. Banerjee、R.V. Venkateswaran

  DOI：10.1016/s0040-4020(01)88398-8

  日期：1990.1

  a known precursor of grandisol (1). The diazoketone 28, on photolysis yielded a mixture of cyclobutane carboxylates 29 and 30. Conversion of the trans acid 31 to a methyl ketone followed by oxidative functionalisation of the phenyl group gave the keto ester 36 which was isomerised under acid catalysis to 37, which in optically active form had been a precursor to (-) grandisol. Photolysis of diazoketone

  重氮酮19在甲醇中的光解提供了环丁烷羧酸酯20。在碳酸氢钠水溶液-THF中的光解以更好的产率提供了酸21。酯的还原，随后的氧化和随后的Wittig反应提供了±junionone （3）。重氮酮24的光解导致环丁烷羧酸酯25的1：1混合物。用氢碘酸处理相应的羧酸提供了双环内酯27，其是大新醇（1）的已知前体。重氮酮28在光解后产生环丁烷羧酸盐29的混合物和30。将反酸31转化为甲基酮，然后对苯基进行氧化官能化，得到酮酯36，其在酸催化下被异构化为37，其以光学活性形式是（-）大丁香酚的前体。重氮酮38的光解提供了2∶1比例的环丁烷羧酸盐39和40。用甲基锂处理并随后乙酰化的相应的酸混合物提供了乙酸酮基酯43和44，从而导致乙酸链烷酰基酯的正式合成（4）。
• Efforts Toward a Synthesis of Crotogoudin and Crotobarin
  作者：Duy Mai、Dmitriy Uchenik、Christopher Vanderwal

  DOI：10.1055/s-0036-1588560

  日期：2017.9

  crotogoudin are discussed, and efforts to achieve each are described. First, a Cope rearrangement/intramolecular Diels–Alder cascade reaction was investigated. Second, a bioinspired sequence of cationic bicyclization and A-ring oxidative fragmentation set-up for a lactonization induced by a phenolic oxidation, ultimately providing a tricyclic intermediate that required only installation of the bridging ring

  讨论了二萜类 crotogoudin 的两种合成设计，并描述了实现每一种的努力。首先，研究了Cope重排/分子内Diels-Alder级联反应。其次，由酚氧化诱导的内酯化的阳离子双环化和 A 环氧化断裂设置的生物启发序列，最终提供了一个三环中间体，只需要安装突出的双环 [2.2.2] 辛烷系统的桥环. 这最后的努力充满了困难，但确实导致了相关酮烯烃通过基于锰（III）的自由基化学环化的条件的发展。
• [EN] PROCESS FOR THE PRODUCTION OF LIPOIC ACID<br/>[FR] PROCEDE DE PRODUCTION D'ACIDE LIPOIQUE
  申请人：ASTA MEDICA AKTIENGESELLSCHAFT

  公开号：WO1996038437A1

  公开（公告）日：1996-12-05

  (EN) A process for the preparation of lipoic acid (thioctic acid), or a derivative thereof, is one in which a 2-substituted cyclohexanone is transformed in an oxidation reaction to a lactone having formula (I), wherein X is a heteroatom substituent.(FR) Cette invention concere un procédé de préparation d'acide lipoïque (acide thioctique) ou d'un de ses dérivés, durant lequel un cyclohexanone 2-substitué est transformé, lors d'une réaction d'oxydation, en un lactone corespondant à la formule (I) où X est un substituant d'hétéroatome.

  一种制备硫辛酸（又名硫辛酸）或其衍生物的方法，其中2-取代环己酮在氧化反应中转化为具有公式（I）的内酯，其中X是杂原子取代基。