(2R,3R)-1,2-epoxy-3-heptanol | 102517-37-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3R)-1,2-epoxy-3-heptanol
• 英文别名: (1R)-1-[(2R)-oxiran-2-yl]pentan-1-ol
• CAS: 102517-37-3
• 化学式: C₇H₁₄O₂
• 分子量: 130.187
• InChiKey: VKMBCHKSMBUPPG-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2R,3R)-1,2-epoxy-3-heptanol 在 咪唑 、 正丁基锂 、 碘 、 magnesium 、 mercury dichloride 作用下， 以 乙醚 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成
  参考文献：
  名称：

  Diastereoselective Formation of Tetrahydrofurans via Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of the C13–C29 Subunit of Amphidinolide N

  摘要：

  An efficient synthesis of the C13-C29 fragment of amphidinolide N is described. The synthesis relies on a new strategy involving Pd-catalyzed asymmetric allylic alkylation to generate diastereoselectively the cis- or trans-THF unit simply by varying the enantiomer of the ligand. The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer.

  DOI：

  10.1021/ol302409g
• 作为产物：
  描述：

  反-2-庚烯-1-醇 在 (DHQD)₂PHAL 、 四氯化碳 、 potassium osmate(VI) dihydrate 、 甲基磺酰胺 、 碳酸氢钠 、 potassium carbonate 、 三苯基膦 、 sodium hydroxide 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 30.0h， 生成 (2R,3R)-1,2-epoxy-3-heptanol
  参考文献：
  名称：

  Diastereoselective Formation of Tetrahydrofurans via Pd-Catalyzed Asymmetric Allylic Alkylation: Synthesis of the C13–C29 Subunit of Amphidinolide N

  摘要：

  An efficient synthesis of the C13-C29 fragment of amphidinolide N is described. The synthesis relies on a new strategy involving Pd-catalyzed asymmetric allylic alkylation to generate diastereoselectively the cis- or trans-THF unit simply by varying the enantiomer of the ligand. The C19 hydroxyl-bearing stereocenter was introduced using a chelation-controlled allylation which led exclusively to a single diastereoisomer.

  DOI：

  10.1021/ol302409g

文献信息

• Enzyme-Triggered Enantioconvergent Transformation of Haloalkyl Epoxides
  作者：Sandra F. Mayer、Andreas Steinreiber、Romano V. A. Orru、Kurt Faber

  DOI：10.1002/1099-0690(200112)2001:23<4537::aid-ejoc4537>3.0.co;2-e

  日期：2001.12

  rac-trans-haloalkyl epoxides 1a−8a using the epoxide hydrolase activity of whole bacterial cells furnished the corresponding vicinal diols 1b−8b as intermediates; these (spontaneously) underwent ring closure to yield cyclic products 1c−6c through an enzyme-triggered cascade reaction. In particular, cis-configured substrates (1a, 3a, 5a, 7a) were transformed in an enantioconvergent fashion, which resulted

  使用整个细菌细胞的环氧水解酶活性对 2,3-二取代外消旋-顺-和外消旋-反-卤代烷基环氧化物 1a-8a 进行生物催化水解，得到相应的邻位二醇 1b-8b 作为中间体；这些（自发地）经历闭环以通过酶触发的级联反应产生环状产物 1c-6c。特别是，顺式构型的底物（1a、3a、5a、7a）以对映收敛方式转化，导致从外消旋体中形成 100% des 和高达 92% ees 的单一立体异构产物。
• Chemoenzymatic asymmetric total syntheses of a constituent of Jamaican rum and of (+)-Pestalotin using an enantioconvergent enzyme-triggered cascade reaction
  作者：Sandra F. Mayer、Andreas Steinreiber、Marian Goriup、Robert Saf、Kurt Faber

  DOI：10.1016/s0957-4166(02)00124-6

  日期：2002.4

  (−)-Pestalotin—was accomplished based on an enzyme-triggered cascade-reaction. Thus, a racemic halomethyl oxirane was hydrolyzed by bacterial epoxide hydrolases to furnish the corresponding vic-halomethyl-diol, which underwent spontaneous ring-closure to furnish an epoxy alcohol in up to 93% e.e. and ≥99 d.e. Due to the fact that this process was enantioconvergent, the occurrence of the undesired enantiomer

  基于酶触发的级联反应，完成了一条短促的化学酶促途径，可产生两种天然产物，第一种是牙买加朗姆酒的成分，第二种是赤霉素增效剂（-）-Pestalotin的（+）-正肽。因此，外消旋卤代甲基环氧乙烷用细菌环氧化物水解酶水解成相应的提供VIC -halomethyl二醇，其经历了自发闭环以提供在向上的环氧醇至93％ee的和≥99德由于这样的事实，这个过程是对映体会聚的，完全避免了不希望的对映异构体的出现。
• Synthesis of the rarely obtained syn-adducts in the reaction of organocopper compounds with 2,3-O-isopropylideneglyceraldehyde. Preparation of optically active epoxy alcohols
  作者：Fumie Sato、Yuichi Kobayashi、Osamu Takahashi、Tsunehisa Chiba、Yoshiyuki Takeda、Masato Kusakabe

  DOI：10.1039/c39850001636

  日期：——

  Organocopper compounds, prepared from Grignard reagents and copper(I) iodide in tetrahydrofuran-dimethyl sulphide, react with 2,3-O-isopropylideneglyceraldehyde highly stereoselectively (>10:1) affording the rarely obtained syn-addition products which can be readily converted into optically active epoxy alcohols, useful intermediates in organic synthesis.

  由格氏试剂和碘化亚铜（I）在四氢呋喃-二甲基硫醚中制备的有机铜化合物与2,3- O-异亚丙基甘油醛高度立体选择性（> 10：1）反应，提供了很少获得的合成加成产物，可以轻松地将其转化为旋光性环氧醇，在有机合成中有用的中间体。
• Enantioselective Synthesis of <i>des</i>-Epoxy-Amphidinolide N
  作者：Barry M. Trost、Wen-Ju Bai、Craig E. Stivala、Christoph Hohn、Caroline Poock、Marc Heinrich、Shiyan Xu、Jullien Rey

  DOI：10.1021/jacs.8b11827

  日期：2018.12.12

  efforts addressed the scalability problem of the southern fragment synthesis and significantly improved the efficiency of the atom-economical Ru AA coupling, but suffered from several protecting group-based issues that proved insurmountable. Finally, relying on a judicious protecting group strategy together with concise fragment preparation, des-epoxy-amphidinolide N was achieved in a convergent fashion

  des-epoxy-amphidinolide N 的合成在 22 个最长的线性步骤和 33 个总步骤中实现。本文报道了三代合成努力。在第一代中，我们的关键拼接策略突出了分子内 Ru 催化的烯烃 - 炔 (Ru AA) 偶联和后期环氧化，证明是成功的，但使用二羟基化方法安装 α,α'-二羟基酮基序有问题。我们的第二代合成工作解决了南片段合成的可扩展性问题，并显着提高了原子经济 Ru AA 偶联的效率，但遇到了几个基于保护基的问题，这些问题被证明是无法克服的。最后，依靠明智的保护组策略以及简洁的片段准备，des-epoxy-amphidinolide N 以收敛的方式实现。计算揭示了amphidinolide N 内的氢键桥。使用我们合成的脱环氧-amphidinolide N 比较13C NMR 化学位移差异表明amphidinolide N 和carbenolide I 可能相同。
• Asymmetric dihydroxylation of primary allylic halides and a concise synthesis of (−)-diepoxybutane
  作者：Koen P.M. Vanhessche、Zhi-Min Wang、K.Barry Sharpless

  DOI：10.1016/s0040-4039(00)73212-6

  日期：1994.5

  Tire asymmetric dihydroxylation (AD) of primary allylic halides is described. Enantiomeric excesses range from 40 to 98%. Subsequent base treatment gives epoxy alcohols in high yields. This strategy is further illustrated by the synthesis of (-)-diepoxybutane, an important C-4-chiral building block.