Methanesulfonic acid (1S,8aS)-6-butyl-6-hydroxy-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester | 123966-87-0

• 英文名称: Methanesulfonic acid (1S,8aS)-6-butyl-6-hydroxy-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
• 英文别名: [(1S,8aS)-6-butyl-6-hydroxy-8a-methyl-1,2,3,4,7,8-hexahydronaphthalen-1-yl] methanesulfonate
• CAS: 123966-87-0
• 化学式: C₁₆H₂₈O₄S
• 分子量: 316.462
• InChiKey: IYZYHGVUQHUDIA-KSCSMHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  72
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  正丁基锂 、 (+/-)-cis-5-mesyloxy-10-methyl-1(9)-octal-2-one 在 copper(I) bromide dimethylsulfide complex 、 三氟化硼乙醚 作用下， 生成 Methanesulfonic acid (1S,8aS)-6-butyl-6-hydroxy-8a-methyl-1,2,3,4,6,7,8,8a-octahydro-naphthalen-1-yl ester
  参考文献：
  名称：

  改性有机铜试剂和高阶铜酸盐的电子转移性质的研究

  摘要：

  引入BF 3 OEt 2或Me 3 SiCl会减弱有机铜试剂的电子转移性能。解释结果与当前的机械方案一致。与相关的低阶铜酸盐相反，高阶基于CuCN的铜酸盐显示出显着的电子转移能力。

  DOI：

  10.1016/0040-4020(89)80079-1

文献信息

• Some Observations on the Mechanism of Diorganocuprate 1,4-Addition Reactions with α,β-Unsaturated Ketones:  Effects of Diethyl Ether in Reactions of Butylcoppers in Toluene
  作者：Celia L. Kingsbury、Robin A. J. Smith

  DOI：10.1021/jo970316y

  日期：1997.7.1

  Mixtures of butyllithium and copper iodide prepared in toluene react with alpha,beta-unsaturated ketones predominantly in a 1,2-fashion. Addition of 2 equiv of diethyl ether to the system results in a dramatic preference for the 1,4-product, as found normally with diorganocuprates in ethereal solvents. These results are in accordance with the theoretical predictions that a suitable ligand is required to facilitate the stabilization of a formally copper(III) reaction intermediate on the 1,4-addition mechanistic pathway.