trans-(2S)-1,2-dihydroxy-3-pentene | 143289-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: trans-(2S)-1,2-dihydroxy-3-pentene
• 英文别名: (+)-(2S,3E)-3-penten-1,2-diol；(3E,2S)-pent-3-ene-1,2-diol；(E,2S)-pent-3-ene-1,2-diol
• CAS: 143289-06-9
• 化学式: C₅H₁₀O₂
• 分子量: 102.133
• InChiKey: WYFGTZBRHKBFBD-HRJJCQLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-(2S)-1,2-dihydroxy-3-pentene 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 (-)-D-dimethyl tartrate 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 18.17h， 生成 (R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(3-methyl-oxiranyl)-ethanol
  参考文献：
  名称：

  Asymmetric epoxidation of chiral allylic alcohols

  摘要：

  Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00327-8
• 作为产物：
  描述：

  methyl (+)-(2S,3E)-2-hydroxypent-3-enoate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到trans-(2S)-1,2-dihydroxy-3-pentene
  参考文献：
  名称：

  Asymmetric epoxidation of chiral allylic alcohols

  摘要：

  Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00327-8

文献信息

• Bacterial Biotransformation of Isoprene and Related Dienes
  作者：Derek R. Boyd、David Clarke、Marcel C. Cleij、John T. G Hamilton、Gary N. Sheldrake

  DOI：10.1007/s007060070096

  日期：2000.6.15

  Pseudomonas putida ML 2 was used in the oxidative biodegradation of the acyclic dienes isoprene, trans -piperylene, cis -piperylene, and 1,3-butadiene. Regioselective dioxygenase-catalyzed dihydroxylation of alkenes yielded vicinal diols in the preferred sequence monosubstituted >  cis -disubstituted >  gem -disubstituted >  trans -disubstituted. The isolated diol metabolites had an excess of the R

   细菌 恶臭假单胞菌 在无环二烯烃的氧化降解，使用ML 2异戊二烯， 反式 -piperylene， 顺 -piperylene，和1,3-丁二烯。区域选择性双加氧酶催化的烯烃的二羟基化产生邻位二醇，优选的顺序为单取代>  顺式- 二取代>  宝石- 二取代>  反式- 二取代。分离出的二醇代谢物具有过量的 R 构型（9–97％ ee ），并通过加入丙二醇作为抑制剂来控制进一步的二醇氧化。使用ML2菌株的立体选择性是由于酶的不对称烯烃二羟基化和二醇的动力学拆分而产生的。 R 构型的烯丙基仲醇基团的对映选择性氧化产生相应的不饱和酮醇 。回收的残留二醇的 S 构型大大过量（≥93％ ee ） 。除了产生不饱和二醇和酮醇的酶二烯氧化步骤之外，还发现了酶烯加氢产生饱和酮醇和二醇的证据。
• Synthesis and bioluminescence-inducing properties of autoinducer (S)-4,5-dihydroxypentane-2,3-dione and its enantiomer
  作者：Manikandan Kadirvel、William T. Stimpson、Souad Moumene-Afifi、Biljana Arsic、Nicola Glynn、Nigel Halliday、Paul Williams、Peter Gilbert、Andrew J. McBain、Sally Freeman、John M. Gardiner

  DOI：10.1016/j.bmcl.2010.02.064

  日期：2010.4

  The autoinducer (4S)-4,5-dihydroxypentane-2,3-dione ((S)-DPD, AI-2) facilitates chemical communication, termed 'quorum sensing', amongst a wide range of bacteria, The synthesis of (S)-DPD is challenging in part due to its instability. Herein we report a novel synthesis of (S)-DPD via (2S)-2,3-O-isopropylidene glyceraldehyde, through Wittig, dihydroxylation and oxidation reactions, with a complimentary asymmetric synthesis to a key precursor. Its enantiomer (R)-DPD, was prepared from D-mannitol via (2R)2,3-O-isopropylideneglyceraldehyde. The synthesized enantiomers of DPD have AI-2 bioluminescenceinducing properties in the Vibrio harveyi BB170 strain. (C) 2010 Elsevier Ltd. All rights reserved.
• Xu, Daqiang; Crispino, Gerard A.; Sharpless, K. Barry, Journal of the American Chemical Society, 1992, vol. 114, # 19, p. 7570 - 7571
  作者：Xu, Daqiang、Crispino, Gerard A.、Sharpless, K. Barry

  DOI：——

  日期：——
• Asymmetric epoxidation of chiral allylic alcohols
  作者：Erwin G.J.C. Warmerdam、Adrianus M.C.H. van den Nieuwendijk、Johannes Brussee、Chris G. Kruse、Arne van der Gen

  DOI：10.1016/0957-4166(96)00327-8

  日期：1996.9

  Two series of chiral allylic alcohols, derived from alpha,beta-unsaturated cyanohydrins, were subjected to asymmetric epoxidation under a variety of conditions. Both achiral (organic peracid, metal-catalyzed peroxide) and chiral (Sharpless titanium-tartrate system) oxidants were applied. Several three and all theoretically possible erythro epoxides were isolated in enantiomerically and diastereomerically pure form. Copyright (C) 1996 Elsevier Science Ltd