4-methylpentyllithium | 113466-79-8

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物
• 英文名称: 4-methylpentyllithium
• 英文别名: isohexyllithium；(4-methyl-pentyl)-lithium
• CAS: 113466-79-8
• 化学式: C₆H₁₃Li
• 分子量: 92.1102
• InChiKey: XTXVFXYCLVASIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.01
• 重原子数：
  7.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  4-methylpentyllithium 在 copper(l) iodide 、 camphor-10-sulfonic acid 、 potassium carbonate 、 一水合肼 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 11.83h， 生成 胆固醇
  参考文献：
  名称：

  Organocuprate-mediated methods for the stereospecific introduction of steroid side chains at C-20

  摘要：

  DOI：

  10.1021/jo00157a002

文献信息

• Reinvestigation of Base-Catalyzed Condensation of Ethyl α,α-Dichloroacetoacetate with Aldehydes. A New Synthesis of (±)-Disparlure
  作者：Sadao Tsuboi、Hiroyuki Furutani、Akira Takeda、Kayoko Kawazoe、Sadao Sato

  DOI：10.1246/bcsj.60.2475

  日期：1987.7

  The titled reaction gave ethyl 2-chloro-2,3-epoxyalkanoates (2) and ethyl 3-chloro-2-oxoalkanoates in improved yields. The structure of the by-product was revised as 1,5-dichloro-4,8-dialkyltricyclo[5.1.0.03,5]octane-2,6-dione by means of the 13C–1H two-dimensional NMR spectrum and an X-ray crystallographic analysis. Compound 2 was applied to the synthesis of (±)-disparlure, the pheromone of the gypsy

  标题反应以提高的产率得到2-氯-2，3-环氧链烷酸乙酯(2)和3-氯-2-氧代链烷酸乙酯。副产物的结构通过 13C–1H 二维核磁共振谱和 X 射线衍射谱修正为 1,5-二氯-4,8-​​二烷基三环[5.1.0.03,5]辛烷-2,6-二酮-射线晶体学分析。化合物 2 用于合成 (±)-disparlure，吉普赛蛾的信息素，通过 6 个步骤以 49% 的总产率合成。
• Asymmetric cleavage of chiral α,β-ethylenic acetals by organolithium reagents
  作者：Alexandre Alexakis、Farida Mhamdi、Franz Lagasse、Pierre Mangeney

  DOI：10.1016/s0957-4166(96)00438-7

  日期：1996.12

  α,β-Ethylenic chiral acetals react regio- and stereoselectively with organolithium reagents. The obtained enol ether may be hydrolyzed into a chiral β-disubstituted aldehyde.

  α，β-乙烯手性缩醛与有机锂试剂在区域和立体上发生反应。可以将获得的烯醇醚水解成手性β-二取代的醛。
• Lipase-catalyzed kinetic resolution of 3-chloro-2-hydroxyalkanoates. Its application for the synthesis of (−)-disparlure
  作者：Sadao Tsuboi、Nobuyuki Yamafuji、Masanori Utaka

  DOI：10.1016/s0957-4166(96)00529-0

  日期：1997.2

  Reduction of 3-chloro-2-oxoalkanoates 1 with NaBH4 gave predominantly syn-3-chloro-2-hydroxyalkanoates 2 (synlanti=91/9-99/1) in 50-97% yields. Resolution of syn-2 by lipase-catalyzed transesterification gave (2S,3S)-2 and (2R,3R)-2-acetoxy-3-chloroalkanoates (2R,3R)-3. Total synthesis of (-)-disparlure, the pheromone of the gypsy moth was established from (2S,3S)-2g via 4 steps in 34.9% overall yield. (C) 1997 Elsevier Science Ltd. All rights reserved.
• Synthesis of alkenes from carbonyl compounds and carbanions alpha to silicon. III. Full report and a synthesis of the sex pheromone of gypsy moth
  作者：T. H. Chan、E. Chang

  DOI：10.1021/jo00936a020

  日期：1974.11
• Discovery of N-Aryl-2-acylindole human glucagon receptor antagonists
  作者：Christopher Sinz、Amy Bittner、Ed Brady、Mari Candelore、Qing Dallas-Yang、Victor Ding、Guoqiang Jiang、Zhen Lin、Sajjad Qureshi、Gino Salituro、Richard Saperstein、Jackie Shang、Deborah Szalkowski、Laurie Tota、Stella Vincent、Michael Wright、Shiyao Xu、Xiaodong Yang、Bei Zhang、James Tata、Ronald Kim、Emma R. Parmee

  DOI：10.1016/j.bmcl.2011.09.105

  日期：2011.12

  A novel class of N-aryl-2-acylindole human glucagon receptor (hGCGR) antagonists is reported. These compounds demonstrate good pharmacokinetic profiles in multiple preclinical species. One compound from this series, indole 33, is orally active in a transgenic murine pharmacodynamic model. Furthermore, a 1 mg/kg oral dose of indole 33 lowers ambient glucose levels in an ob/ob/hGCGR transgenic murine diabetes model. This compound was deemed suitable for preclinical safety studies and was found to be well tolerated in an 8-day experimental rodent tolerability study. The combination of preclinical efficacy and safety observed with compound 33 highlights the potential of this class as a treatment for type 2 diabetes. (C) 2011 Elsevier Ltd. All rights reserved.