(S)-2,2-diethyl-1,3-dioxolane-4-methanol | 117677-39-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (S)-2,2-diethyl-1,3-dioxolane-4-methanol
• 英文别名: [(4S)-2,2-diethyl-1,3-dioxolan-4-yl]methanol
• CAS: 117677-39-1
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: WEIVFXLGBXCVEF-ZETCQYMHSA-N

物化性质

• 沸点：
  221.6±15.0 °C(Predicted)
• 密度：
  2 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  (S)-2,2-diethyl-1,3-dioxolane-4-methanol 、 对甲苯磺酰氯 以75%的产率得到
  参考文献：
  名称：

  FUGANTI, GLAUDIO;GRASSELLI, PIERO;SERVI, STEFANO;LAZZARINI, AMERIGA;CASAT+, TETRAHEDRON, 44,(1988) N 9, 2575-2582

  摘要：

  DOI：
• 作为产物：
  描述：

  4--2,2-diethyl-1,3-dioxolane 以 六甲基磷酰三胺 、 水 为溶剂， 反应 1.5h， 生成 (S)-2,2-diethyl-1,3-dioxolane-4-methanol
  参考文献：
  名称：

  Enzymatic resolution of 2,2-disubstituted-1,3-dioxolane-4-methanol carboxylic esters

  摘要：

  The enantioselectivity of enzymatic hydrolysis of carboxylic esters of various 1,2-ketals of glycerol has been investigated. The influence of the ketal group has been studied. A number of lipases and proteinases have been tested and the best enantioselectivity was obtained with proteinase from Aspergillus oryzae which gave an E-value of 9 with 2,2-dimethyl-1,3-dioxolane-4-methanol butanoate. Variations in the acyl part revealed that butanoyl was optimal. All hydrolysis products have been synthesised in homochiral forms from homochiral starting materials.

  DOI：

  10.1016/s0957-4166(00)82313-7

文献信息

• 2,3-<i>O</i>-(3-Pentylidene)-D-glyceraldehyde and 2,3-<i>O</i>-(3-Pentylidene)-L-glyceraldehyde: Convenient Glyceraldehyde Surrogates Obtained via a Novel Periodate-Based Oxdation System
  作者：Christopher R. Schmid、David A. Bradley

  DOI：10.1055/s-1992-26170

  日期：——

  The synthesis of two novel glyceraldehyde surrogates, 2,3-O-(3-pentylidene)-D-glyceraldehyde (2) and 2,3-O-(3-pentylidene)-L.-glyceraldehyde (3) is presented. Synthesis, handling and storage advantages of 2 and 3 over the conventionally employed 2,3-O-isopropylidene-D-glyceraldehyde (1) are discussed. The 3-pentanone-derived protecting group facilitates the extraction of product from aqueous oxidation solutions, while the 3-pentanone liberated on ketal deprotection can be efficiently removed at reduced pressures. The synthesis employs a buffered potassium periodate oxidation which offers significant advantages over sodium periodate in glycol cleavage reactions.

  报道了两种新型甘油醛替代物，2,3-O-(3-戊叉)-D-甘油醛（2）和2,3-O-(3-戊叉)-L-甘油醛（3）的合成。与传统使用的2,3-O-异亚丙基-D-甘油醛（1）相比，讨论了2和3在合成、处理和储存方面的优点。由3-戊酮衍生的保护基团有助于从水相氧化溶液中提取产物，而在缩酮去保护时释放的3-戊酮可以在减压下有效去除。该合成采用缓冲的高碘酸钾氧化，相较于高碘酸钠在二醇裂解反应中具有显著优势。
• A process for the preparation of R and S-2,2-R1,R2-1,3-dioxolane-4-methanol
  申请人：GIST-BROCADES N.V.

  公开号：EP0244912A1

  公开（公告）日：1987-11-11

  Process for the preparation of R-2,2-R1, R2-1,3-dioxo- lane-4-methanol wherein R1 and R2 are H or alkyl groups or wherein R, and R2 together with the carbon atom to which they are attached form a carbocyclic ring by subjecting a mixture of R- and S-2,2-R1, R2-1,3-dioxolane-4-methanol to the action of a micro-organism or substances derived therefrom having the ability for stereoselective consumption of S-2,2-R1, R2-1,3-dioxolane-4-methanol preferably until at least 80 wt% and more preferably all the S-2,2-R1, R2-1,3-dioxolane-4-methanol is consumed. Various micro-organisms of the genus Rhodococcus, Nocardia and Corynebacterium are disclosed as suitable for the purpose. The R-isomer is a valuable intermediate for stereospecific synthesis of various biologically active compounds including S-metoprolol.

  制备R-2,2-R1, R2-1,3-二氧戊环-4-甲醇的工艺 其中R1和R2为H或烷基或其中R和R2连同它们所连接的碳原子形成一个碳环 将R-和S-2,2-R1, R2-1、3-二氧戊环-4-甲醇的微生物或由其衍生的物质的作用下，具有立体选择性消耗 S-2,2-R1,R2-1,3-二氧戊环-4-甲醇的能力，优选直到至少消耗 80%，更优选全部 S-2,2-R1,R2-1,3-二氧戊环-4-甲醇。已公开的 Rhodococcus、Nocardia 和 Corynebacterium 属的各种微生物都适用于这一目的。R 异构体是立体特异性合成各种生物活性化合物（包括 S-美托洛尔）的重要中间体。
• 3,5-Dihydroxy-6,8-nonadienoic acids and derivatives as hypocholesterolemic agents
  申请人：PFIZER INC.

  公开号：EP0312269A2

  公开（公告）日：1989-04-19

  A compound for use in lowering blood cholesterol having the relative stereochemical formula:- wherein R is hydrogen, (C₁-C₃)alkyl, phenyl, benzyl or a conventional radical forming an ester group which is hydrolyzable under physiological conditions; R¹ and R², when taken separately, and R₃ are each independently hydrogen, (C₁-C₃)alkyl, benzyl, naphthyl, phenyl or phenyl mono or disubstituted with the same or different substituents selected from the group consisting of F, Cl, Br, I, (C₁-C₃)alkyl, CF₃, (C₁-C₃)alkoxy, benzyl and phenyl; with the proviso that at least one of R¹ and R² is other than hydrogen or (C₁-C₃)alkyl; and R¹ and R², when taken together, are combined with the double bonded carbon atom which they are attached to form a diradical ylidene group of the formula wherein n is 0 or 1 and Y is oxygen, OCH₂, sulfur, SCH₂, methylene or ethylene; or a pharmaceutically acceptable cationic salt thereof when R is hydrogen.

  一种用于降低血液胆固醇的化合物，其相对立体化学式为 其中 R 是氢、(C₁-C₃)烷基、苯基、苄基或形成在生理条件下可水解的酯基的常规基团； R¹和 R² 分别独立地为氢、(C₁-C₃)烷基、苄基、萘基、苯基或苯基单胞、苯基或被选自 F、Cl、Br、I、(C₁-C₃)烷基、CF₃、(C₁-C₃)烷氧基、苄基和苯基的相同或不同取代基单取代或二取代的苯基；但 R¹ 和 R² 中至少有一个不是氢或 (C₁-C₃)烷基；以及 当 R¹ 和 R² 结合在一起时，与它们所连接的双键碳原子结合形成式中的二叉亚 乙基 其中 n 为 0 或 1，Y 为氧、OCH₂、硫、SCH₂、亚甲基或亚乙基；或 当 R 为氢时，其药学上可接受的阳离子盐。
• Verfahren zur Herstellung von enantiomereneinen 2,2,4-trisubstituierten 1,3-Dioxolanen
  申请人：LONZA AG

  公开号：EP0325967A2

  公开（公告）日：1989-08-02

  Verfahren zur Herstellung von enantiomerenreinen 2,2-disub­stituierten 1,3-Dioxolan-4-methanolen oder N,2,2-trisubsti­tuierten 4-Aminomethyl-1,3-dioxolanen aus den entsprechenden cyclischen Ketalen der Erythron- oder Threonsäure oder deren Salzen durch elektrochemische oxidative Decarboxylierung und anschliessende Reduktion oder reduktive Aminierung.

  通过电化学氧化脱羧和随后的还原或还原胺化反应，从相应的赤藓酸或苏氨酸环酮或其盐制备对映体纯度为 2,2-二取代的 1,3-二氧戊环-4-甲醇或 N,2,2-三取代的 4-氨基甲基-1,3-二氧戊环的工艺。
• Terao, Yoshiyasu; Tsuji, Keiichiro; Murata, Masakazu, Chemical and pharmaceutical bulletin, 1989, vol. 37, # 6, p. 1653 - 1655
  作者：Terao, Yoshiyasu、Tsuji, Keiichiro、Murata, Masakazu、Achiwa, Kazuo、Nishio, Toshiyuki、et al.

  DOI：——

  日期：——