1'-ethylpropyl 3-hydroxy-2-methylpentanoate | 211621-52-2

• 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: 1'-ethylpropyl 3-hydroxy-2-methylpentanoate
• 英文别名: 1-ethylpropyl 3-hydroxy-2-methylpentanoate；1'-ethylpropyl-3-hydroxy-2-methylpentanoate；1-Ethylpropyl-2-methyl-3-hydroxypentanoate；pentan-3-yl 3-hydroxy-2-methylpentanoate
• CAS: 211621-52-2
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: JZOCRUBSQNZLIW-UHFFFAOYSA-N

物化性质

• 沸点：
  283.4±13.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1'-ethylpropyl 3-hydroxy-2-methylpentanoate 在 chromium(VI) oxide 、 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 葡萄糖 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 16.0h， 生成 (2S, 3R)-1-ethylpropyl 3-(3,5-dinitrobenzoyloxy)-2-methylpentanoate
  参考文献：
  名称：

  A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester

  摘要：

  The microbial reduction of 1'-ethylpropy 2-methyl-3-oxopentanoate, a beta-keto ester possessing bulky substituent, as well as the corresponding enol ester was examined. Epimeric mixture of hydroxy ester, containing (2S,3S)-isomer as the major product (92%e.e., 43%d.e.) was obtained via the reduction of enol ester with growing cells of Pichia farinosa IAM 4682 in 63% yield. The resulting-beta-hydroxy ester was converted to (2S,3R)-isomer (88%e.e., 96%d.e.), of which e.e. was further enhanced by the lipase-catalyzed partial hydrolysis of the corresponding chloroacetate to give (-)-sitophilate, (99%e.e.) an aggregation pheromone of Sitophillus granarius L.

  DOI：

  10.1016/s0040-4020(01)89726-x
• 作为产物：
  描述：

  2-甲基-3-氧代戊酸乙酯 在 sodium tetrahydroborate 作用下， 以 正己烷 为溶剂， 反应 72.0h， 生成 1'-ethylpropyl 3-hydroxy-2-methylpentanoate
  参考文献：
  名称：

  Sitophilate的简明和立体选择性化学酶法合成，Sitophilus granarius（L.）由雄性产生的聚集信息素。

  摘要：

  （2 S，3 R）-Sitophilate，即谷类象鼻虫Sitophilus granarius（L.）的雄性产生的聚集信息素，是使用新型化学酶方法立体选择性地制备的，总收率为50％。合成设计的基础是用金黄色葡萄球菌（CCM H1）菌株将2-甲基-3-氧戊酸乙酯的对映选择性真菌还原，然后在C3进行Mitsunobu转化。合成序列的最后一步是使用无溶剂条件下的微波辐射，使用市售的南极假丝酵母B脂肪酶（CaL B，Novozym 435）进行的脂肪酶介导的酯交换反应。

  DOI：

  10.1016/j.tetasy.2013.08.004

文献信息

• A Flexible Stereocontrolled Synthesis of β-Hydroxy-α-methyl Esters: Application to the Synthesis of Stegobiol and Serricorole
  作者：Pilar Gil、Jesús Razkin、Alberto González

  DOI：10.1055/s-1998-2052

  日期：1998.4

  β-Hydroxy-α-methyl esters have been obtained in a stereocontrolled manner and high enantiomeric and diastereomeric purity from commercially available methyl 3-oxopentanoate and methyl 3-oxobutanoate. The key step is the catalytic hydrogenation of the carbonyl group using (R)- or (S)-BINAP-Ru as chiral catalyst followed by asymmetric alkylation. Stegobiol and serricorole, components of the sex pheromone of the drugstore beetle, Stegobium paniceum (L.) and cigarette beetle, Lasioderma serricorne (F.), have been prepared from these chiral building blocks without the need for stoichiometric amounts of chiral auxiliaries.

  利用市售的甲基3-氧代戊酸酯和甲基3-氧代丁酸酯，可以通过立体控制的方式合成具有高对映异构体纯度和非对映异构体纯度的β-羟基-α-甲酯。关键步骤是使用手性催化剂(R)-或(S)-BINAP-Ru对羰基进行催化氢化，随后进行不对称烷基化。药物甲虫（Stegobium paniceum L.）和烟甲虫（Lasioderma serricorne F.）的性信息素成分Stegobiol和Serricorole就是从这些手性构建模块中合成的，无需使用等量的手性辅助剂。
• <i>Geotrichum candidum</i>Assisted Synthesis of Sitophilate, Male Aggregation Pheromone of Granary Weevil
  作者：Hemalata M. Puntambekar、Dattatraya G. Naik

  DOI：10.1080/00397919808004291

  日期：1998.7

  Abstract The syntheses of optically inactive Sitophilate and the optically active isomers (2S, 3S) and (2S, 3R) were completed by a simple route using easily avilable starting compounds.

  摘要 使用容易获得的起始化合物，通过简单的途径完成了无旋光的 Sitophilate 和旋光异构体 (2S, 3S) 和 (2S, 3R) 的合成。
• Stereoselective chemoenzymatic synthesis of sitophilate: a natural pheromone
  作者：Dimitris Kalaitzakis、Spiros Kambourakis、David J. Rozzell、Ioulia Smonou

  DOI：10.1016/j.tetasy.2007.10.008

  日期：2007.10

  The aggregation pheromone of the granary weevil Sitophilus granarius, (2S,3R)-1-ethylpropyl 3-hydroxy-2-methylpentanoate, has been synthesized in 63% total isolated yield and high chemical and enantiomeric purity (98% de, > 99% ee) from readily available methyl 3-oxopentanoate. A stereoselective ketone reduction followed by an ester hydrolysis, were the two key steps of the synthesis and were both performed by commercially available enzymes. (c) 2007 Elsevier Ltd. All rights reserved.
• A concise and stereoselective chemoenzymatic synthesis of Sitophilate, the male-produced aggregation pheromone of Sitophilus granarius (L.)
  作者：Silvana P. Ravía、Mariela Risso、Santiago Kröger、Silvana Vero、Gustavo A. Seoane、Daniela Gamenara

  DOI：10.1016/j.tetasy.2013.08.004

  日期：2013.10

  (2S,3R)-Sitophilate, the male-produced aggregation pheromone of the granary weevil Sitophilus granarius (L.) was prepared stereoselectively using a novel chemoenzymatic approach in 50% overall yield. The synthetic design was based on an enantioselective fungal reduction of ethyl 2-methyl-3-oxopentanoate with a strain of Aureobasidium pullulans (CCM H1), followed by a Mitsunobu inversion at C3. The

  （2 S，3 R）-Sitophilate，即谷类象鼻虫Sitophilus granarius（L.）的雄性产生的聚集信息素，是使用新型化学酶方法立体选择性地制备的，总收率为50％。合成设计的基础是用金黄色葡萄球菌（CCM H1）菌株将2-甲基-3-氧戊酸乙酯的对映选择性真菌还原，然后在C3进行Mitsunobu转化。合成序列的最后一步是使用无溶剂条件下的微波辐射，使用市售的南极假丝酵母B脂肪酶（CaL B，Novozym 435）进行的脂肪酶介导的酯交换反应。
• A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester
  作者：Takeshi Sugai、Daisuke Sakuma、Naoki Kobayashi、Hiromichi Ohta

  DOI：10.1016/s0040-4020(01)89726-x

  日期：1991.8

  The microbial reduction of 1'-ethylpropy 2-methyl-3-oxopentanoate, a beta-keto ester possessing bulky substituent, as well as the corresponding enol ester was examined. Epimeric mixture of hydroxy ester, containing (2S,3S)-isomer as the major product (92%e.e., 43%d.e.) was obtained via the reduction of enol ester with growing cells of Pichia farinosa IAM 4682 in 63% yield. The resulting-beta-hydroxy ester was converted to (2S,3R)-isomer (88%e.e., 96%d.e.), of which e.e. was further enhanced by the lipase-catalyzed partial hydrolysis of the corresponding chloroacetate to give (-)-sitophilate, (99%e.e.) an aggregation pheromone of Sitophillus granarius L.