methyl (R)-5-tosyloxy-3-methylpentanoate | 96924-72-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (R)-5-tosyloxy-3-methylpentanoate
• 英文别名: methyl (3R)-3-methyl-5-(4-methylphenyl)sulfonyloxypentanoate
• CAS: 96924-72-0
• 化学式: C₁₄H₂₀O₅S
• 分子量: 300.376
• InChiKey: BRECTDFATUTAAE-GFCCVEGCSA-N

物化性质

• 沸点：
  409.6±28.0 °C(Predicted)
• 密度：
  1.169±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (R)-5-tosyloxy-3-methylpentanoate 在 氢氧化钾 作用下， 以 甲醇 、 乙醚 、 水 为溶剂， 反应 14.5h， 生成 (R)-3-methyloctanoic acid
  参考文献：
  名称：

  Carpita, Adriano; Magistris, Elisabetta De; Rossi, Renzo, Gazzetta Chimica Italiana, 1989, vol. 119, # 2, p. 99 - 106

  摘要：

  DOI：
• 作为产物：
  描述：

  β-甲基戊二酸单甲酯 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 22.5h， 生成 methyl (R)-5-tosyloxy-3-methylpentanoate
  参考文献：
  名称：

  从对映体纯的甲基氢甲基（R）-3-甲基戊二酸酯开始合成在Howardi上不可分离的Diabrotica的性信息素的两个对映体和其他信息素的手性前体

  摘要：

  现成的甲基氢（R）-3-甲基戊二酸甲酯（2）是用于合成几种生物活性化合物的有用的手性结构单元。对映体纯的（R）-2已被用于立体定向合成10-甲基-2- tretcanone的两个对映体1a和1b，这是南部玉米根虫性信息素Diabrotica undecimpunctata howardi Barber的性信息素。化合物（R）-2也已用于制备99％光学纯度（R）-3-甲基-1-戊醇（6）和对映体纯度（R）-5-甲基-异三甲苯胺（7）。这些化合物是适用于进一步修饰成其他手性昆虫信息素的有用的结构单元。

  DOI：

  10.1016/s0040-4020(01)96510-x

文献信息

• Analysis of the Labial Gland Secretion of the Cuckoo-Bumblebee (Psithyrus vestalis) Males and Synthesis of Abundant Geranylcitronellol
  作者：Irena Valterová、Aleš Svatoš、Oldřich Hovorka

  DOI：10.1135/cccc19961501

  日期：——

  Labial glands of the cuckoo-bumblebee males of the species Psithyrus vestalis were extracted and the components of their secretions were identified. Chemical composition of the males' signal of Psithyrus vestalis has not yet been described in the literature. We found geranycitronellyl acetate to be the main component (48%). Geranylcitronellol and (Z)-15-eicosen-1-ol were present in the secretion in lower amounts. Long-chain aldehydes, acetates, and hydrocarbons formed only minor components of the mixture. The identification of minor components was based on GC-MS, while the more abundant compounds were isolated and fully characterized by spectral and chemical methods. For the structure confirmation, geranylcitronellol was prepared from geranyl bromide via a three-step synthesis.

  雄性寄生锤头蜂种群Psithyrus vestalis 的唇腺被提取，并且识别了它们分泌物的成分。文献中尚未描述Psithyrus vestalis 雄性信号的化学成分。我们发现柠檬醛香茅醇醋酸酯是主要成分（48%）。柠檬醛香茅醇和(Z)-15-十五碳-1-醇以较少的量存在于分泌物中。长链醛类、醋酸酯和烃类仅构成混合物的微量成分。通过GC-MS鉴定了微量成分，而更丰富的化合物则通过光谱和化学方法进行了分离和全面表征。为了确认结构，柠檬醛香茅醇通过三步合成从柠檬基溴制备而成。
• Imidazolidinone compounds
  申请人：——

  公开号：US20040116476A1

  公开（公告）日：2004-06-17

  This invention relates to compounds of the following formula: 1 in which R 1 , R 2 , A 1 , A 2 , X, Y, m, n, p, x and y are as defined herein, pharmaceutical compositions comprising the compounds and use of the compounds in treating enterovirus infection.

  本发明涉及以下式子的化合物：1其中R1，R2，A1，A2，X，Y，m，n，p，x和y如此定义，以及包含这些化合物的药物组成物和使用这些化合物治疗肠道病毒感染。
• Synthesis and antipicornavirus activity of (R)- and (S)-1-[5-(4′-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one
  作者：Jyh-Haur Chern、Chih-Shiang Chang、Chia-Liang Tai、Yen-Chun Lee、Chung-Chi Lee、Iou-Jiun Kang、Ching-Yin Lee、Shin-Ru Shih

  DOI：10.1016/j.bmcl.2005.06.069

  日期：2005.10

  The new pyridyl imidazolidinone derivative, 1-[5-(4'-chlorobiphenyl-4-yloxy)-3-methylpentyl]-3-pyridin-4-yl-imidazolidin-2-one (+/-)-1a, was synthesized and found to have an excellent antiviral activity against EV71 (IC50 = 0.009 mu M). Therefore, both the enantiomers, (S)-(+)-1a and (R)-(-)-1a, have been prepared starting from readily available monomethyl (R)-3-methylglutarate (7) as a useful chiral building block and their antiviral activity was evaluated in a plaque reduction assay. Interestingly, we observed that the enantiomer (S)-(+)-1a was 10-fold more active against enterovirus71 (EV71) (IC50 = 0.003 mu M) than the corresponding enantiomer (R)-(-)-1a (IC50 = 0.033 mu M). Similar results were found against all five strains (1743, 2086, 2231, 4643, and BrCr) of EV71 tested. This demonstrated that the absolute configuration of the chiral carbon atom at the 3-position of the alkyl linker considerably influenced the anti-EV71 activity of these pyridyl imidazolidinones. (c) 2005 Elsevier Ltd. All rights reserved.
• CARPITA, ADRIANO;DE, MAGISTRIS ELISABETTA;ROSSI, RENZO, GAZZ. CHIM. ITAL., 119,(1989) N, C. 99-105
  作者：CARPITA, ADRIANO、DE, MAGISTRIS ELISABETTA、ROSSI, RENZO

  DOI：——

  日期：——
• US7501445B2
  申请人：——

  公开号：US7501445B2

  公开（公告）日：2009-03-10