methyl (2S,3R)-3-(1H-indol-3-yl)-2-acetoxybutanoate | 149494-89-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: methyl (2S,3R)-3-(1H-indol-3-yl)-2-acetoxybutanoate
• 英文别名: methyl (2S,3R)-2-acetyloxy-3-(1H-indol-3-yl)butanoate
• CAS: 149494-89-3
• 化学式: C₁₅H₁₇NO₄
• 分子量: 275.304
• InChiKey: MLFKRMCWAISVBL-OTYXRUKQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (2S,3R)-3-(1H-indol-3-yl)-2-acetoxybutanoate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.33h， 以87%的产率得到methyl (2S,3R)-3-(1H-indol-3-yl)-2-hydroxybutanoate
  参考文献：
  名称：

  A concise synthesis of (−)-indolmycin and (−)-5-methoxyindolmycin

  摘要：

  Concise syntheses of (-)-indolmycin 1 and (-)-5-methoxyindolmycin 3 were developed based on a palladium-catalyzed reaction of (2S,3R)-2-acetoxy-3-methyl-5-trimethylsilyl-4-pentynoate 6 with an o-iodoaniline derivative 10 or 11, followed by reaction with guanidine hydrochloride in the presence of base. An optically active internal alkyne (2S 3R)-6 was obtained by lipase-assisted enantioselective acetylation of (+/-)-(2,3)-syn-2-hydroxy-3-methyl-5-trimethylsily-4-pentynoate 4. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.013
• 作为产物：
  描述：

  methyl (2S,3R)-3-{1-(tert-butoxycarbonyl)-2-(trimethylsilyl)-1H-indol-3-yl}-2-acetoxybutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到methyl (2S,3R)-3-(1H-indol-3-yl)-2-acetoxybutanoate
  参考文献：
  名称：

  A concise synthesis of (−)-indolmycin and (−)-5-methoxyindolmycin

  摘要：

  Concise syntheses of (-)-indolmycin 1 and (-)-5-methoxyindolmycin 3 were developed based on a palladium-catalyzed reaction of (2S,3R)-2-acetoxy-3-methyl-5-trimethylsilyl-4-pentynoate 6 with an o-iodoaniline derivative 10 or 11, followed by reaction with guanidine hydrochloride in the presence of base. An optically active internal alkyne (2S 3R)-6 was obtained by lipase-assisted enantioselective acetylation of (+/-)-(2,3)-syn-2-hydroxy-3-methyl-5-trimethylsily-4-pentynoate 4. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.07.013

文献信息

• An Amphiphile-Lipase Aggregate Bearing 1,2-Dialkylated Mannitol Ether as a New Type of Immobilized Enzyme in Organic Solvents.
  作者：Hiroyuki AKITA、Keisuke KATO、Isao UMEZAWA、Hiroko MATSUKURA

  DOI：10.1248/cpb.45.2085

  日期：——

  Neutral amphiphiles of a new type corresponding to 1, 2-dialkylated mannitol ethers (6-10) were synthesized. Amephiphile-lipase aggregates were found to function as an immobilized enzyme system for enantioselective acetylation or enantioselective hydrolysis of α-hydroxy esters or α-acetoxy esters, respectively, in organic solvents.

  合成了对应于1,2-二烷基化甘露醇醚(6-10)的新型中性两亲分子。发现两亲分子-脂肪酶聚集体能在有机溶剂中分别作为固定化酶系统用于α-羟基酯的对映选择性乙酰化或α-乙酰氧基酯的对映选择性水解。
• Enantioselective Acetylation of an .ALPHA.-Hydroxy Ester by Using Ether-Linked Lipid-Lipase Aggregates in Organic Solvents.
  作者：Hiroyuki AKITA、Isao UMEZAWA、Djadjat TISNADJAJA、Hiroko MATSUKURA、Takeshi OISHI

  DOI：10.1248/cpb.41.16

  日期：——

  Phospholipids of a new type having ω-cyclohexyltridecyl groups were synthesized in order to investigate the influence of the structure of lipophilic part of phospholipids upon the enzymatic reaction. Enantioselective acetylation of an α-hydroxy ester was carried out in the presence of lipid-lipase aggregates bearing O-ω-cyclohexyltridecyl and O-hexadecyl groups. The chemical yield of α-acetoxy ester was improved by using lipid-lipase aggregates compared to the case of enzymatic reaction using native lipase OF-360 from Candida cylindracea. It was found that the influence of the ω-cyclohexyltridecyl group on the chemical and optical yields of α-acetoxy ester was essentially the same as that to the hexadecyl group.

  为了研究磷脂亲脂部分的结构对酶反应的影响，我们合成了具有ω-环己基十三烷基的新型磷脂。在含有 O-ω-环己基十三烷基和 O-十六烷基的脂质脂肪酶聚集体存在下，对 α-羟基酯进行了对映体选择性乙酰化。与使用来自圆柱形念珠菌的原生脂肪酶 OF-360 进行酶反应的情况相比，使用脂质脂肪酶聚集体提高了 α-乙酰氧基酯的化学产率。研究发现，ω-环己基十三烷基对 α-乙酰氧基酯的化学产率和光学产率的影响与对十六烷基的影响基本相同。