1,1-diethoxy-3-hydroxy-2-(hydroxymethyl)propane | 40364-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,1-diethoxy-3-hydroxy-2-(hydroxymethyl)propane
• 英文别名: 2-diethoxymethyl-propane-1,3-diol；3-hydroxy-2-hydroxymethyl-propionaldehyde diethyl acetal；3,3-diethoxy-2-(hydroxymethyl)-1-propanol；2-(Diethoxymethyl)propane-1,3-diol
• CAS: 40364-79-2
• 化学式: C₈H₁₈O₄
• 分子量: 178.229
• InChiKey: NVCQBZCYRXZJPK-UHFFFAOYSA-N

物化性质

• 沸点：
  294.1±35.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,1-diethoxy-3-hydroxy-2-(hydroxymethyl)propane 在 硫酸 作用下， 生成 2-羟甲基丙烯醛
  参考文献：
  名称：

  Vik,J.-E., Acta Chemica Scandinavica (1947), 1973, vol. 27, p. 239 - 250

  摘要：

  DOI：
• 作为产物：
  描述：

  diethoxymethylmalonic acid diethyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 1,1-diethoxy-3-hydroxy-2-(hydroxymethyl)propane
  参考文献：
  名称：

  Vik,J.-E., Acta Chemica Scandinavica (1947), 1973, vol. 27, p. 239 - 250

  摘要：

  DOI：

文献信息

• Stereocontrolled synthesis of the C-1 to C-7 fragment of erythronolide A. A model study using the 1,7-dioxaspiro[5.5]undecane system
  作者：Gilles Sauvé、David A. Schwartz、Luc Ruest、Pierre Deslongchamps

  DOI：10.1139/v84-496

  日期：1984.12.1

  A partir de l'oxo-3 heptene-6oate de methyle, synthese du propionate de dioxa-1,7spiro [5.5] undecene-2methanol-3; ce compose est ensuite transforme en benzyloxy-3 α,γ-dimethyl β-hydroxy methyl-3 dioxa-1,7spiro [5.5] undecanebutyrate-2 de methyle possedant les 5 centres chiraux contigus que l'on retrouve dans l'acide seco de l'erythronolide A

  a partir de l'oxo-3 heptene-6oate demethyle，合成 du propionate de dioxa-1,7spiro [5.5] undecene-2methanol-3；ce compose est ensuite transforme en benzyloxy-3 α,γ-dimethyl β-hydroxymethyl-3 dioxa-1,7spiro [5.5] undecanebutyrate-2 demethyle possedant les 5 centre chiraux contigus que l'on retrouve dans l'acide seco de L'erythronolide A
• Enantioselective preparation of asymmetrically protected 2-propanoyl-1,3-propanediol derivatives: toward the total synthesis of Kazusamycin A
  作者：Noriyoshi Arai、Noriko Chikaraishi、Mitsuhiro Ikawa、Satoshi Ōmura、Isao Kuwajima

  DOI：10.1016/j.tetasy.2004.01.007

  日期：2004.2

  The preparation of enantiomerically pure 2-propanoyl-1,3-propanediol derivatives, key intermediates in our studies on total synthesis of the potent antitumor compound Kazusamycin A are described. After various enzymatic protocols for desymmetrization of the prochiral diol were studied, it was found that these compounds could be prepared in 97–98% ee by means of an enzymatic kinetic resolution.

  描述了对映体纯的2-丙酰基-1,3-丙二醇衍生物的制备方法，这是我们对有效的抗肿瘤化合物卡祖霉素A进行全合成研究的关键中间体。在研究了多种用于手性二醇去对称化的酶促方案后，发现可以通过酶促动力学拆分以97–98％ee的方式制备这些化合物。
• Procedure for making trimethylolmethane
  申请人：The United States of America as represented by the Secretary of the Navy

  公开号：US04091040A1

  公开（公告）日：1978-05-23

  A process for the production of trimethylolmethane in high yields. Trimetolmethane is useful as the essential precurser to trimethylolmethane trinitrate, a high-energy plasticizer and explosive.

  该过程用于高产量生产三甲基甲醇。三甲基甲醇是制备高能塑化剂和爆炸物三甲基甲醇硝酸酯的必要前体。
• Nielsen, Arnold T.; Moore, Donald W.; Schuetze, Bryan D., Polish Journal of Chemistry, 1981, vol. 55, # 6, p. 1393 - 1403
  作者：Nielsen, Arnold T.、Moore, Donald W.、Schuetze, Bryan D.

  DOI：——

  日期：——
• Synthesis and lipase-catalyzed asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal acetals
  作者：Gabriella Egri、Elemér Fogassy、Lajos Novák、László Poppe

  DOI：10.1016/s0957-4166(97)00018-9

  日期：1997.2

  Prochiral dialkylacetal derivatives of 3-hydroxy-2-hydroxymethylpropanal 6a-e were synthesized from the corresponding 2-substituted diethyl malonates 5a-e and subjected to asymmetric enzymatic acetylation. The diethyl malonates 5a-f were prepared from diethyl chloromethylenemalonate 3 by using either a one- or a two-step process. Asymmetric acetylation of 3-hydroxy-2-hydroxymethylpropanal diethyl acetal 6b with several enzymes was studied first, showing the highest enantiotopic selectivity with lipase from Pseudomonas fluorescens (PfL). Solvent effect was also investigated: the best selectivity was obtained in a mixture of hexane and diethyl ether. Furthermore, several other acetals 6a-e were also tested under the optimal acetylation conditions. (C) 1997 Elsevier Science Ltd.