3-(1,3-二氧杂烷-2-基)丙醛 | 82962-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 中文名称: 3-(1,3-二氧杂烷-2-基)丙醛
• 英文名称: 3-(1,3-dioxolan-2-yl)propanal
• 英文别名: 1,3-dioxolane-2-propanal
• CAS: 82962-18-3
• 化学式: C₆H₁₀O₃
• mdl: MFCD00971290
• 分子量: 130.144
• InChiKey: XFMMMZDHPNOERJ-UHFFFAOYSA-N

物化性质

• 沸点：
  201.5±15.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.833
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932999099

反应信息

• 作为反应物：
  描述：

  3-(1,3-二氧杂烷-2-基)丙醛 在 2,6-二甲基吡啶 、 正丁基锂 、 ammonia borane 、 C₃₀H₄₂N₄OS 、 sodium cyanoborohydride 、 二异丙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 50.16h， 生成
  参考文献：
  名称：

  使用有机催化对映体（+）-arborescidine C和相关的四环吲哚生物碱的对映选择性全合成†

  摘要：

  通过与雅各布森型硫脲有机催化剂进行Pictet-Spengler环化反应的关键步骤，可以实现包括自然存在的化合物（+）-碳硼烷C和（+）-碳硼烷B在内的四环吲哚的简明和对映选择性合成。合成工艺在锅经济策略中得到了进一步证明，并在一锅操作中得以实现。

  DOI：

  10.1039/c7ob00473g
• 作为产物：
  描述：

  1,3-二氧戊环-2-丙-1-醇 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到3-(1,3-二氧杂烷-2-基)丙醛
  参考文献：
  名称：

  Stereocontrolled Synthesis of Functionalized Bicyclic α-Methylene Butyrolactones via Tungsten-Mediated Intramolecular Allylation of Aldehydes

  摘要：

  The syntheses of a series of CpW(CO)(2)(pi-gamma-lactonyl) complexes bearing a tethered aldehyde are described. These pi-allyl complexes are prepared as either syn- or anti-stereoisomers. Treatment of these dicarbonyl complexes with NOBF4 and NaI in CH3CN effects an intramolecular allylation of the tethered aldehyde, yielding bicyclic alpha-methylene butyrolactones comprising a homoallylic alcohol. Both syn- and anti-isomers of tungsten-pi-allyl compounds produce the same alpha-methylene butyrolactones. The cyclizations proceed with high diastereoselectivities to give only the cis-fused bicyclic gamma-lactones. The preference for cis-fused stereoselection can be rationalized based on a tricyclic transition state mechanism.

  DOI：

  10.1021/jo9909002

文献信息

• Synthesis of (7<i>S</i>,15<i>S</i>)- and (7<i>R</i>,15<i>S</i>)-Dolatrienoic Acid^1a
  作者：Jonathan J. Duffield、George R. Pettit

  DOI：10.1021/np000502q

  日期：2001.4.1

  stereospecific synthesis of (7S,15S)- and (7R,15S)-dolatrienoic acids (2) was achieved using an approach consisting of 16 linear steps. The C-11--C-16 unit was prepared in seven steps from ethyl (S)-lactate and coupled using a trans-selective Wittig--Schlosser reaction to the C-7--C-10 fragment. Chirality at the C-7 position was introduced using an Evan's-type chiral auxiliary in a cobalt-mediated Reformatsky

  （7S，15S）-和（7R，15S）-十二碳三烯酸（2）的立体有择合成是使用由16个线性步骤组成的方法实现的。C-11--C-16单元是从（S）-乳酸乙酯中分七个步骤制备的，并使用反式Wittig-Schlosser反应与C-7-C-10片段偶联。在钴介导的Reformatsky反应中，使用Evan's型手性助剂在C-7位置引入手性，得到（3S，11S）-醛24。随后与Wittig反应，由三步反应得到的酸形成acid盐， （7S，15S）-十二碳三烯酸，强癌细胞生长抑制性环二肽dolastatin 14（1）的四种非对映异构体之一。第二种非对映异构体（7R，15S）-十二碳三烯酸
• Stereoselective Synthesis of Piperidines by Iridium-Catalyzed Cyclocondensation
  作者：Tobias Sandmeier、Simon Krautwald、Erick M. Carreira

  DOI：10.1002/anie.201706374

  日期：2017.9.11

  An iridium-catalyzed cyclocondensation of amino alcohols and aldehydes is reported. Intramolecular allylic substitution by an enamine intermediate and subsequent in situ reduction furnishes 3,4-disubstituted piperidines with high enantiospecificity and good diastereoselectivity. The modular approach and the broad functional group tolerance provide access to diverse piperidine derivatives, which were

  据报道，铱催化的氨基醇和醛的环缩合反应。用烯胺中间体进行分子内烯丙基取代和随后的原位还原，提供了具有高对映体特异性和良好非对映选择性的3,4-二取代哌啶。模块化方法和广泛的官能团耐受性使人们可以使用各种哌啶衍生物，并将其进一步官能化以提供多种用途的产品。
• Process for the production of tryptophane-hydantoin
  申请人：Degussa Aktiengesellschaft

  公开号：US04374995A1

  公开（公告）日：1983-02-22

  Tryptophane hydantoin is prepared by (a) reacting a compound of the general formula ##STR1## where A is an alkylene group having 2 or 3 carbon atoms or such an alkylene group substituted by 1 to 2 methyl groups in aqueous or aqueous alcoholic solution with hydrogen cyanide or a cyanide ion supplying compound, ammonia or an ammonium ion supplying compound and carbon dioxide or a carbonate ion supplying compound and (b) reacting the reaction mixture obtained with phenyl hydrazine at a pH between 0.1 and 4.

  色氨酸咪唑酮是通过以下步骤制备的：(a) 在水或水醇溶液中，将一般式##STR1##中A为含有2或3个碳原子的烷基基团或这样的烷基基团中的1至2个甲基基团进行反应，与氰化氢或供应氰离子的化合物、氨或供应铵离子的化合物以及二氧化碳或供应碳酸根离子的化合物反应；(b) 将得到的反应混合物在pH值为0.1至4的条件下与苯基肼反应。
• Electroactive and luminescent polymers: new fluorene-heterocycle-based hybrids
  作者：Barbara Tsuie、Jerry L. Reddinger、Gregory A. Sotzing、Jadwiga Soloducho、Alan R. Katritzky、John R. Reynolds

  DOI：10.1039/a903374b

  日期：——

  The synthesis, characterization, and electrochromic properties of copolymers derived from 9,9-dialkyl-2,7-dibromofluorene (18a, alkyl=C 10 H 21 ; 24, alkyl=Et) and pyrrole, thiophene, 3,4-ethylenedioxythiophene, and furan are described. Two synthetic routes to 9,9-diethyl-2,7-bis(pyrrol-2-yl)fluorene (30) afford product in 30% and 20% yields, respectively. Monomer 30 undergoes electropolymerizationto yield electroactive polymer films. The lowest monomer oxidation potential (E p,m =0.4 V vs. Ag/Ag + ) is found in tetraethylammonium tosylate (TEATOS)-CH 3 CN, but film formation is slow. Spectroelectrochemical analysis of poly(30) reveals a band gap at 2.4 eV and upon polymer oxidation, two low energy absorptions peaking at 1.2 and 2.2 eV appear. This phenomenon is attributed to formation of bipolaron bands between the valence and conduction bands. Soluble fluorene-heterocycle polymers 34a-d have been synthesized by the Stille coupling reaction of 18a and 2,5-bis(trimethylstannyl)thiophene (21a), 5,5′-bis(trimethylstannyl)-2,2′-bithiophene (21b), 2,5-bis(trimethylstannyl)-3,4-ethylenedioxythiophene (21c), and 2,5-bis(trimethylstannyl)furan (22), respectively, in high yields. The NMR spectra are consistent with the proposed structures of the polymers 34a-d, and no evidence of ring opening of the furyl unit in 34d is seen in the NMR and IR spectra. The molecular weights of 34a-d are in the range of 8000 g mol –1 with polydispersity indices (PDI) of 2. Polymers 34a-c have band gaps measured at 2.4 eV, while polymer 34d has its gap at 2.6 eV. Polymers 34a-c undergo solution doping with SbCl 5 to form new low energy bipolaron bands at the expense of the absorption in the UV-VIS. However, polymer 34d does not oxidatively dope with SbCl 5 .

  描述了从9,9-二烷基-2,7-二溴芴（18a，烷基=C10H21；24，烷基=Et）和吡咯、噻吩、3,4-亚乙基二氧噻吩以及呋喃衍生的共聚物的合成、表征和电致变色性质。两条合成9,9-二乙基-2,7-双（吡咯-2-基）芴（30）的路线分别获得了30%和20%的产率。单体30经电化学聚合生成电活性聚合物薄膜。最低单体氧化电位（Ep,m=0.4 V vs. Ag/Ag+）在四乙基铵对甲苯磺酸盐（TEATOS）-CH3CN中观察到，但薄膜形成缓慢。光谱电化学分析发现聚30的带隙为2.4 eV，聚合物氧化后出现两个低能量吸收峰，峰值为1.2 eV和2.2 eV，这一现象归因于价带和导带之间双极化子带的形成。通过Stille偶联反应，18a分别与2,5-双（三甲基锡基）噻吩（21a）、5,5′-双（三甲基锡基）-2,2′-双噻吩（21b）、2,5-双（三甲基锡基）-3,4-亚乙基二氧噻吩（21c）和2,5-双（三甲基锡基）呋喃（22）反应，合成了可溶性芴-杂环聚合物34a-d，产率较高。NMR光谱与所提出的聚合物34a-d的结构一致，NMR和IR光谱中未观察到34d中呋喃单元的开环证据。34a-d的分子量在8000 g mol–1范围内，多分散性指数（PDI）为2。聚合物34a-c的带隙测得为2.4 eV，而聚合物34d的带隙为2.6 eV。聚合物34a-c通过溶液掺杂SbCl5形成新的低能量双极化子带，以牺牲紫外-可见光吸收为代价。然而，聚合物34d不能通过SbCl5进行氧化掺杂。
• Synthetic routes to bis(pyrrolyl)arylenes. Experimental and molecular modeling studies
  作者：Jadwiga Sołoducho、Szczepan Roszak、Antoni Chyla、Krzysztof Tajchert

  DOI：10.1039/b101731o

  日期：——

  The synthesis and characterization of compounds derived from 9,9-dialkylfluorene and 1,4-dioxane[3,4-b]thiophene are described. The key step involves a modified Steglich reaction between 9,9-dialkyl-2,7-N,N′-diallyliminochlorofluorene or 2,5-N,N′-diallyliminochloroethylenedioxythiophene and tert-BuOK (Route 1). Route 2 for bis(pyrrol-2-yl)dioxanethiophene, involving the reaction between 1,4-dioxane[2,3-c]thiophene and a dioxolanepropanol, is also a useful and general strategy. Molecular modeling studies indicate relationships between the molecular parameters (structure, ionization potential, atomic charges) of the synthesized moieties and their polymerization properties.

  描述了从9,9-二烷基芴和1,4-二氧杂[3,4-b]噻吩衍生的化合物的合成与表征。关键步骤涉及9,9-二烷基-2,7-N,N′-二烯基亚氯芴或2,5-N,N′-二烯基亚氯乙烯二氧噻吩与叔丁基氢氧化钾之间的改进Steglich反应（路线1）。路线2针对双（吡咯-2-基）二氧杂噻吩，涉及1,4-二氧杂[2,3-c]噻吩与二氧杂环丙醇的反应，也是一种有效且通用的策略。分子模拟研究表明，合成部分的分子参数（结构、离子化势、原子电荷）与其聚合特性之间存在关系。