4-formyl-2,2,5,5-tetramethyl-1,3-dioxolane | 90137-21-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-formyl-2,2,5,5-tetramethyl-1,3-dioxolane
• 英文别名: 2,2,5,5-tetramethyl-1,3-dioxolane-4-carbaldehyde
• CAS: 90137-21-6
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: XJLDRHDSLAHIFD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-formyl-2,2,5,5-tetramethyl-1,3-dioxolane 以 乙醚 为溶剂， 反应 334.0h， 生成 (3RS,4SR,5RS)-2-benzyl-4-methoxycarbonyl-5-methyl-3-<(4RS)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl>isoxazolidine
  参考文献：
  名称：

  Fray, M. Jonathan; Jones, Richard H.; Thomas, Eric J., Journal of the Chemical Society. Perkin transactions I, 1985, p. 2753 - 2762

  摘要：

  DOI：
• 作为产物：
  描述：

  3-methylbut-2-enyl 4-nitrobenzoate 在 光气 、 potassium osmate(VI) dihydrate 、 水 、 N-甲基吗啉氧化物 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 为溶剂， 反应 58.0h， 生成 4-formyl-2,2,5,5-tetramethyl-1,3-dioxolane
  参考文献：
  名称：

  Preparation and use of enantioenriched 2-aryl-propylsulfonylbenzene derivatives as valuable building blocks for the enantioselective synthesis of bisabolane sesquiterpenes

  摘要：

  We have demonstrated that different enantioenriched 2-arylpropylsufonylbenzene derivatives are very useful building blocks for the synthesis of aromatic bisabolane sesquiterpenes. Their preparation and the exploitation of their chemical reactivity have been comprehensively investigated. Accordingly, the naturally occurring bisabolane sesquiterpenes (-)-curcuphenol, (-)-xanthorrhizol, (+)-glandulone A, (+)-curcudiol, (+)-turmerone and (+)-curcudiol-10-one were synthesized in high enantiomeric purity. It is worth noting that the compounds (+)-curcudiol-10-one and (+)-glandulone A were prepared in enantioenriched form for the first time. Through the proposed synthetic approaches, we were able to confirm both chemical structures and the absolute configurations previously assigned to the two aforementioned sesquiterpenes. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.10.016

文献信息

• Synthesis of (all-E,2R,2?R)-oscillol
  作者：Bruno Traber、Hanspeter Pfander

  DOI：10.1002/hlca.19960790217

  日期：1996.3.20

  Optically active (all-E,2R,2′R)-oscillol (= (all-E,2R,2′R)-3,4,3′,4′-tetradehydro-1,2,1′,2′-tetrahydro-ψ,ψ-carotene-1,2,1′,2′-tetrol; 1) was synthesized according to the C10 + C20 + C10 = C40 strategy, applying the Wittig reaction to couple the synthons 4 and 6. The chiral centre was introduced by a Sharpless dihydroxylation of 3-methylbut-2-enyl 4-nitrobenzoate (8).

  光学活性的（清一色ë，2 - [R，2' - [R）-oscillol（=（清一色ë，2 - [R，2' - [R）-3,4,3'，4'-四脱氢1,2,1'，根据C 10 + C 20 + C 10 = C 40策略合成2'-tetrahydro-ψ，ψ-胡萝卜素-1,2,1'，2'-tetrol; 1），采用Wittig反应偶联合成子4和6。通过3-甲基丁-2-烯基4-硝基苯甲酸酯的无尖锐的二羟基化作用引入手性中心（8）。
• Aspects of nitrile oxide cycloaddition stereoselectivity: Chemistry of 4-cyano-2,2-dimethyl- and 4-cyano-2,2,5,5-tetramethyl-1,3-dioxolane oxides. X-ray structure of (4 , 5)-4,5-bismethoxy-carbonyl-3-[(4)-2,2,5,5-tetramethyl-1,3-dioxolan-4-yl]-Δ2-isox-azoline
  作者：Richard H. Jones、Gareth C. Robinson、Eric J. Thomas

  DOI：10.1016/0040-4020(84)85117-0

  日期：1984.1

  4-Cyano-2,2-dimethl- and 4-cyano-2,2,5,5-tetramethyl-1,3-dioxolane oxìdes (1) and (2) were generated from the corresponding chloro-oximes, and trapped by addition to styrene, dimethyl maleate, dimethyl fumarate, and cyclopentene. The additions to styrene and dimethyl fumarate gave 1 : 1 mixtures of diastereoisomeric adducts. However some stereoselectivity was detected in the additions to the -1,2-disubstituted

  由相应的氯代肟生成4-氰基-2,2-二甲基-和4-氰基-2,2,5,5-四甲基-1,3-二氧戊环肟（1）和（2），并被捕获除了苯乙烯，马来酸二甲酯，富马酸二甲酯和环戊烯。将苯乙烯和富马酸二甲酯加成，得到非对映异构体加合物的1：1混合物。然而，在-1，2-二取代的烯烃的加成物中检测到一些立体选择性。的结构（4 ，5 ）-4,5- bismethoxycarbonyl -3 - [（4 ）-2,2,5,5- tetramethyldioxolan -4-基]-Δ 2 -isoxazoline（17）是由一个X-建立射线结构确定。
• Pyridin-2-YL-Amino-1, 2, 4-Thiadiazole Derivatives as Glucokinase Activators for the Treatment of Diabetes Mellitus
  申请人：Aicher Thomas Daniel

  公开号：US20100204240A1

  公开（公告）日：2010-08-12

  Provided are compounds of Formula (I): wherein R 2 , R 3 , R 13 , L and D 2 are as defined in the specification, which are useful in the treatment and/or prevention of diseases or disorders mediated by deficient levels of glucokinase activity or which can be treated by activating glucokinase including, but not limited to, diabetes mellitus, impaired glucose tolerance, IFG (impaired fasting glucose) and IFG (impaired fasting glycemia), as well as other diseases and disorders such as those discussed herein.

  提供的化合物式(I)如下：其中R2、R3、R13、L和D2如规范中所定义，这些化合物可用于治疗和/或预防由于葡萄糖激酶活性不足引起或可以通过激活葡萄糖激酶治疗的疾病或紊乱，包括但不限于糖尿病、糖耐量受损、IFG（空腹血糖受损）和IFG（空腹高血糖），以及本文所讨论的其他疾病和紊乱。
• Pyridin-2YL-Amino-1, 2, 4-Thiadiazole Derivatives as Glucokinase Activators for the Treatment of Diabetes Mellitus
  申请人：AICHER Thomas Daniel

  公开号：US20120277242A1

  公开（公告）日：2012-11-01

  Provided are compounds of Formula (I): wherein R 2 , R 3 , R 13 , L and D 2 are as defined in the specification, which are useful in the treatment and/or prevention of diseases or disorders mediated by deficient levels of glucokinase activity or which can be treated by activating glucokinase including, but not limited to, diabetes mellitus, impaired glucose tolerance, IFG (impaired fasting glucose) and IFG (impaired fasting glycemia), as well as other diseases and disorders such as those discussed herein.

  本发明提供了式(I)的化合物：其中R2、R3、R13、L和D2如规范中所定义，它们在治疗和/或预防由葡萄糖激酶活性不足介导的疾病或疾病中有用，或者可以通过激活葡萄糖激酶来治疗，包括但不限于糖尿病、糖耐量受损、IFG（空腹血糖受损）和IFG（空腹高血糖），以及其他疾病和疾病，如在此处所讨论的。
• INTERMEDIATES FOR THE PREPARATION OF PYRIDIN-2-YL-AMINO-1,2,4-THIADIAZOLE DERIVATIVES
  申请人：Array BioPharma Inc.

  公开号：US20150057448A1

  公开（公告）日：2015-02-26

  Provided are intermediates having the formulas wherein R 2 , R 3 , and L are as defined in the specification, which are useful in the preparation of pyridin-2-yl-amino-1,2,4-thiadiazole derivatives.

  提供了中间体的公式，其中R2，R3和L的定义如规范中所述，这些中间体在制备吡啶-2-基氨基-1,2,4-噻二唑衍生物中很有用。