(R)-3-acetoxynonanoic acid | 119103-81-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-3-acetoxynonanoic acid
• 英文别名: (R)-β-acetoxynonanoic acid；(3R)-3-acetyloxynonanoic acid
• CAS: 119103-81-0
• 化学式: C₁₁H₂₀O₄
• 分子量: 216.277
• InChiKey: KVVQPHYHAFUWLT-SNVBAGLBSA-N

物化性质

• 沸点：
  325.3±25.0 °C(Predicted)
• 密度：
  1.036±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-3-acetoxynonanoic acid 在 吡啶 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 (R)-3-((R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionyloxy)-nonanoic acid methyl ester
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2
• 作为产物：
  描述：

  (R)-(1-苄基)庚基乙酸酯 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 乙腈 为溶剂， 反应 8.0h， 生成 (R)-3-acetoxynonanoic acid
  参考文献：
  名称：

  Application of microbial enantiofacially selective hydrolysis in natural product synthesis

  摘要：

  Pichinia farinosa IAM 4682 mediated enantiofacially selective hydrolysis worked efficiently (65-70% yield) on the interface-bioreactor in a reproducible manner, which established the product, (R)-2-benzylcyclohexanone (84-87%e.e.), to be the starting material for the synthesis of optically active natural products. Methyl (R)3-hydroxy-12- methyltridecanoate. a constituent of lipopolysaccharide, and (R)-1,3-nonanediol, a secretion of cucumber fly, were synthesized via this common intermediate, of which the optically active secondary alcohol moiety was derived from the above chiral ketone by Baeyer-Villiger oxidation. Final products were enantiomerically enriched to 94-95% e.e., by the lipase-mediated enantioselective transesterification which could remove the minor enantiomer as the corresponding acetate.

  DOI：

  10.1016/s0957-4166(00)86269-2

文献信息

• Recycling Mitsunobu coupling: a shortcut for troublesome esterifications
  作者：Boudjema Menhour、Firmin Obounou Akong、Patrick Mayon、Karen Plé、Sandrine Bouquillon、Stéphan Dorey、Christophe Clément、Magali Deleu、Dominique Harakat、Arnaud Haudrechy

  DOI：10.1016/j.tet.2016.09.065

  日期：2016.11

  An unusual recycling Mitsunobu reaction proved to be successful to couple two fragments in the course of the synthesis of the hydrophobic moiety of rhamnolipid derivatives. Based on the obtained pivotal intermediate, a one pot ‘cross-metathesis/reduction’ approach gave access to structural variations of the side chains. Further study of these molecules will contribute to a better understanding of the

  在鼠李糖脂衍生物的疏水部分的合成过程中，不寻常的循环Mitsunobu反应被证明可以成功地偶联两个片段。基于获得的关键中间体，一锅“交叉复分解/还原”方法使人们可以接触到侧链的结构变化。这些分子的进一步研究将有助于更好地理解脂质部分在免疫刺激和植物防御引发特性中的作用。
• Optically active compound having XI-valerolactone ring and liquid
  申请人：Mitsubishi Rayon Company Ltd.

  公开号：US05045228A1

  公开（公告）日：1991-09-03

  An optically active compound having a .delta.-valerolactone ring which is a ferroelectric liquid crystal and is represented by the following general formula (I): ##STR1## wherein m is an integer of from 1 to 8, Z is a group represented by the following formula: ##STR2## in which each of l and k is a number of 1 or 2 and l and k satisfy the requirement of 2.ltoreq.(l+k).ltoreq.3, X stands for a direct bond, ##STR3## Y stands for ##STR4## and A.sub.1 and A.sub.2 independently stand for --H, --F or --Cl, ##STR5## R stands for ##STR6## in which n is an integer of from 1 to 18, and * indicates the asymmetric carbon atom.

  具有.delta.-戊内酯环的光学活性化合物，为铁电液晶，其通式（I）如下所示：其中m为1至8的整数，Z为以下通式所代表的基团：其中l和k各自为1或2的数字，且l和k满足2≤(l+k)≤3，X代表直接键，Y代表，A.sub.1和A.sub.2独立地代表--H，--F或--Cl，R代表，其中n为1至18的整数，*表示不对称碳原子。
• Optically active compound having delta-valerolactone ring and liquid crystal composition comprising same
  申请人：MITSUBISHI RAYON CO., LTD.

  公开号：EP0313379B1

  公开（公告）日：1992-07-22
• US5045228A
  申请人：——

  公开号：US5045228A

  公开（公告）日：1991-09-03