threo-2,3-Dimethyl-penten-(1)-ol-(4) | 1502-86-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: threo-2,3-Dimethyl-penten-(1)-ol-(4)
• 英文别名: (2RS,3SR)-3,4-dimethyl-pent-4-en-2-ol；(2S,3R)-3,4-dimethylpent-4-en-2-ol
• CAS: 1502-86-9；1502-87-0；77103-97-0
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: DWYATCNTXOUFFG-RQJHMYQMSA-N

物化性质

• 沸点：
  149.1±9.0 °C(Predicted)
• 密度：
  0.832±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  threo-2,3-Dimethyl-penten-(1)-ol-(4) 在 lithium 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 [(R)-1,1-Di-tert-butyl-3-((1R,2S)-2-ethoxymethoxy-1-methyl-propyl)-3-methyl-siletan-(2Z)-ylidene]-(4-nitro-phenyl)-amine
  参考文献：
  名称：

  Diastereoselective Silacyclopropanations of Functionalized Chiral Alkenes

  摘要：

  Lithium reduction of di-tert-butyldichlorosilane and thermal silylene transfer (105-125 degrees C) are complementary methods for the highly diastereoselective silacyclopropanations of a range of functionalized chiral olefins to afford complex silacycles. We have shown that functionalized cyclohexenes, cyclopentenes, norbornenes, and 1,1-disubstituted alkenes undergo silacyclopropanation with excellent diastereoselectivity (92:8 to >99:1). Our results demonstrate that steric interactions, rather than oxygen-directing effects, control the approach of the silylene or silylenoid intermediate to the olefin. We believe that the sterically demanding nature of the di-tert-butylsilylene species prevents coordination to the oxygen functionality. Thermal silylene transfer conditions exhibit broad functional group tolerance; the elevated temperatures for silylene transfer, however, cannot be employed for the silacyclopropanation of substituted cyclohexenes and 1,1-disubstituted alkenes. Elaboration of the resulting functionalized silacyclopropanes provides an efficient route to polyoxygenated products.

  DOI：

  10.1021/ja020183k
• 作为产物：
  描述：

  异丙烯基溴化镁 、 2,3-cis-epoxybutane 在 copper(l) cyanide 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 threo-2,3-Dimethyl-penten-(1)-ol-(4)
  参考文献：
  名称：

  Diastereoselective Silacyclopropanations of Functionalized Chiral Alkenes

  摘要：

  Lithium reduction of di-tert-butyldichlorosilane and thermal silylene transfer (105-125 degrees C) are complementary methods for the highly diastereoselective silacyclopropanations of a range of functionalized chiral olefins to afford complex silacycles. We have shown that functionalized cyclohexenes, cyclopentenes, norbornenes, and 1,1-disubstituted alkenes undergo silacyclopropanation with excellent diastereoselectivity (92:8 to >99:1). Our results demonstrate that steric interactions, rather than oxygen-directing effects, control the approach of the silylene or silylenoid intermediate to the olefin. We believe that the sterically demanding nature of the di-tert-butylsilylene species prevents coordination to the oxygen functionality. Thermal silylene transfer conditions exhibit broad functional group tolerance; the elevated temperatures for silylene transfer, however, cannot be employed for the silacyclopropanation of substituted cyclohexenes and 1,1-disubstituted alkenes. Elaboration of the resulting functionalized silacyclopropanes provides an efficient route to polyoxygenated products.

  DOI：

  10.1021/ja020183k

文献信息

• Stereochimie de quelques reactions entre aldehydes et reactifs de Grignard satures et allyliques
  作者：H. Felkin、Y. Gault、G. Roussi

  DOI：10.1016/s0040-4020(01)92953-9

  日期：1970.1

  γ-dimethylallyl magnesium bromides) and secondary alkyl [s-butyl magnesium bromide and (1,2-dimethylpropyl) magnesium chloride] Grignard reagents to form pairs of diastereoisomeric alcohols R′—CHMeCHOH—R (R′ = CH2CH, CH2CMe, Et and iPr, respectively). The reactions involving the secondary alkyl Grignard reagents are not stereoselective; those involving the allylic Grignard reagents show some stereoselectivity

  醛R-CHO（R = Me，Et，iPr，tBu）与烯丙基（巴豆基和β，γ-二甲基烯丙基溴化镁）和仲烷基[仲丁基溴化镁和（1,2-二甲基丙基）氯化镁]反应试剂以形成非对映异构的醇对R'-CHMeCHOH-R（R'= CH 2 = CH 3，CH 2 = CMe E，Et和iPr）。涉及二级烷基格氏试剂的反应不是立体选择性的；反之亦然。那些涉及烯丙基格利雅试剂的试剂显示出一定的立体选择性，其方向和大小取决于试剂和醛的结构。
• DULCERE, J. -P.;SANTELLI, M., ISR. J. CHEM., 1985, 26, N 2, 152-156
  作者：DULCERE, J. -P.、SANTELLI, M.

  DOI：——

  日期：——