(2R)-ethyl-1-nonanol

• 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: (2R)-ethyl-1-nonanol
• 英文别名: (2R)-2-ethylnonan-1-ol
• 化学式: C₁₁H₂₄O
• 分子量: 172.311
• InChiKey: GGJSWHVQHRPELC-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  12
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  壬烯 、 三乙基铝 在 bis(1-(-)-neomenthylindenyl)zirconium dichloride 、 氧气 作用下， 以 二氯甲烷 为溶剂， 反应 50.0h， 以70%的产率得到
  参考文献：
  名称：

  Catalytic enantioselective ethylalumination of terminal alkenes: substrate effects and absolute configuration assignment

  摘要：

  The chemo- and enantioselectivity of the reaction of alkenes with AlEt3 catalyzed by bis(1-neomenthyl-indenyl)zirconium dichloride has been studied. The reaction with linear alkenes in a chlorinated solvent (CH2Cl2) gives mainly carbometallation products in 70-80% yield and with enantiomeric purity of 47-70%ee with an (S)-configuration. In the case of vinylcycloalkanes and styrene, the reaction provides roughly equal amounts of carbometallation products and substituted alumolanes with enantioselectivities of 39-69%ee and 40-57%ee, respectively.(R)-MTPA and (R)-2-phenylselenopropionic acid [(R)-PSPA] were used as the derivatization reagents for enantiomeric excess estimation and the absolute configuration assignment of beta-chiral primary alcohols and 2-substituted 1,4-butanediols resulting from oxidation and hydrolysis of the organoaluminum products. It was shown that the specific rotation changes sign in the series of enantiomerically enriched 2-ethyl-1-alkanols when going from beta-ethyl-substituted octanol to nonanol. The conformational analysis of the MTPA and PSPA esters of 2-ethyl-1-alkanols was performed and a dependence of their conformational composition on the type of substituent at the beta-stereogenic center was established. Calculation of the Se-77 NMR chemical shifts of the possible conformers of the PSPA esters demonstrated that the conformation of the selenium moiety has the most pronounced effect on the delta(Se) value. The high efficiency of PSPA application for the enantiomeric purity estimation and the absolute configuration assignment of 2-ethyl-1-alkanols is shown. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.11.019

文献信息

• Octanoic acid derivative to treat fibromyalgia and other pains
  申请人：Warner-Lambert Company LLC

  公开号：EP2172197A1

  公开（公告）日：2010-04-07

  The invention relates to the use of (3S,5R)-3-aminomethyl-5-methyloctanoic acid, or a pharmaceutically acceptable salt thereof, for the manufacture of a medicament for the treatment of a mammal for a disorder selected from fibromyalgia, abdominal or gynaecological pain, and pain caused by increased bladder contractions.

  本发明涉及使用(3S,5R)-3-氨甲基-5-甲基辛酸或其药学上可接受的盐制造一种药物，用于治疗哺乳动物的一种疾病，该疾病选自纤维肌痛、腹痛或妇科疼痛以及膀胱收缩加剧引起的疼痛。