methyl 3-(2-furyl)-3-hydroxy-2-methylpropanoate | 85199-57-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl 3-(2-furyl)-3-hydroxy-2-methylpropanoate
• 英文别名: anti-methyl 2-methyl-3-hydroxy-3-(2-furyl)propanoate；methyl (2S,3R)-3-(furan-2-yl)-3-hydroxy-2-methylpropanoate
• CAS: 85199-57-1；85199-59-3；85199-60-6；85199-61-7；91487-27-3；121350-44-5
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: OCFIKAHRHHYLGN-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-(2-furyl)-3-hydroxy-2-methylpropanoate 在 吡啶 、 双氧水 、 臭氧 作用下， 生成 (2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of functionalized chiral synthons via microbiological reduction

  摘要：

  DOI：

  10.1016/s0040-4039(00)88693-1
• 作为产物：
  描述：

  methyl 3-(furan-2-yl)-2-methyl-3-oxopropanoate 反应 92.0h， 以77%的产率得到methyl 3-(2-furyl)-3-hydroxy-2-methylpropanoate
  参考文献：
  名称：

  Furuichi, Akiya; Akita, Hiroyuki; Koshiji, Hiroko, Agricultural and Biological Chemistry, 1984, vol. 48, # 1, p. 219 - 220

  摘要：

  DOI：

文献信息

• Water-Accelerated Aldol Reaction of Ketene Silyl Acetals with Carbonyl Compounds
  作者：Teck-Peng Loh、Li-Chun Feng、Lin-Li Wei

  DOI：10.1016/s0040-4020(00)00630-x

  日期：2000.9

  The aldol reactions of ketene silyl acetals with reactive aldehydes proceed smoothly in water to afford the corresponding aldol products in good yields.

  乙烯酮甲硅烷基缩醛与反应性醛的醛醇缩合反应在水中可顺利进行，从而以高收率得到相应的醛醇缩合产物。
• Highly Stereoselective Aldol Reaction of Chiral 3-(<i>p</i>-Tolylsulfinyl)furfural with Silyl Ketene Acetal Catalyzed by Lanthanide Triflate
  作者：Yoshitsugu Arai、Tsutomu Masuda、Yukio Masaki

  DOI：10.1055/s-1997-1068

  日期：——

  The aldol reaction of optically active 3-(p-tolylsulfinyl)furfural with silyl ketene acetal catalyzed by a lanthanide triflate proceeded smoothly to give the syn- and anti-aldol products with high diastereoselectivities in high yield.

  在三镧系元素催化下，光学活性 3-(对甲苯亚磺酰基)糠醛与硅酮缩醛的醛醇反应顺利进行，以高非对映选择性和高产率得到了合成和反醛醇产物。
• The use of microorganisms in organic synthesis. III. Microbiological asymmetric reduction of methyl 3-(2-furyl)-2-methyl-3-oxopropionate.
  作者：HIROYUKI AKITA、AKIYA FURUICHI、HIROKO KOSHIJI、KOKI HORIKOSHI、TAKESHI OISHI

  DOI：10.1248/cpb.32.1333

  日期：——

  Microbiological asymmetric reduction of methyl 3-(2-furyl)-2-methyl-3-oxopropionate (5) by various yeasts was carried out. Four kinds of methyl 3-(2-furyl)-3-hydroxy-2-methyl propionates (6a-6d) could be obtained separately from the prochiral β-keto ester 5 by reduction with properly selected microorganisms. In particular, the desired syn-isomer 6a was obtained with high optical purity (>99% e.e.). Both the chemical yield and the optical purity of the reduction products (6a-6d) were significantly improved when fermentation was carried out on a large scale using a 30 1 jar fermentor or a 200 1 tank.

  对甲基3-(2-呋喃基)-2-甲基-3-氧代丙酸酯（5）进行了微生物不对称还原。通过用适当选择的微生物进行还原，可以从手性前体β-酮酯5中分别得到四种甲基3-(2-呋喃基)-3-羟基-2-甲基丙酸酯（6a-6d）。特别是，所希望的顺式异构体6a获得了高光学纯度（>99% e.e.）。当使用30 1罐发酵器或200 1罐进行大规模发酵时，还原产物（6a-6d）的化学产率和光学纯度都得到了显著提高。
• Wittig rearrangement of allyl and propargyl furfuryl ethers leading to 2-furylmethanol derivatives
  作者：Masayoshi Tsubuki、Teruyoshi Kamata、Hiroyuki Okita、Mayumi Arai、Atsushi Shigihara、Toshio Honda

  DOI：10.1039/a907312d

  日期：——

  The first example of the Wittig rearrangement of furfuryl ethers is presented and its application to the preparation of 3-(2-furyl)-3-hydroxy-2-methylpropionates is described.

  提出了糠基醚维蒂希重排的第一个例子，并描述了其在制备 3-(2-呋喃基)-3-羟基-2-甲基丙酸酯中的应用。
• Generation of (<i>E</i>)-Silylketene Acetals in a Rhodium-DuPhos Catalyzed Two-Step Reductive Aldol Reaction
  作者：Cun-Xiang Zhao、Jonathan Bass、James P. Morken

  DOI：10.1021/ol016279l

  日期：2001.9.1

  [GRAPHICS]Mechanistic studies employing in situ NMR analysis implicate intermediate silicon enolates as reactive intermediates in the Rh-DuPhos catalyzed two-step reductive aldol reaction with Cl2MeSiH. These enolates undergo noncatalyzed reaction with a variety of aldehydes to give the derived syn-aldol adduct in high yields and diastereoselection.