(S)-3-(prop-1-en-2-yl)-6-methyl-1,5-cyclohexadienyl trimethylsilyl ether | 423764-66-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (S)-3-(prop-1-en-2-yl)-6-methyl-1,5-cyclohexadienyl trimethylsilyl ether
• 英文别名: {[(3S)-3-isopropenyl-6-methyl-cyclohexa-1,5-dienyl]oxy}(trimethyl)silane；trimethyl-[(3S)-6-methyl-3-prop-1-en-2-ylcyclohexa-1,5-dien-1-yl]oxysilane
• CAS: 423764-66-3
• 化学式: C₁₃H₂₂OSi
• 分子量: 222.403
• InChiKey: JDANSBUFJJUXTK-LBPRGKRZSA-N

物化性质

• 沸点：
  247.9±40.0 °C(Predicted)
• 密度：
  0.89±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-(prop-1-en-2-yl)-6-methyl-1,5-cyclohexadienyl trimethylsilyl ether 在 盐酸 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 1.33h， 生成 (R)-5-Isopropenyl-6-methoxymethoxy-2-methyl-cyclohex-2-enone
  参考文献：
  名称：

  Hirai, Yoshimasa; Ito, Kennosuke; Nagaoka, Hiroto, Heterocycles, 1998, vol. 48, # 2, p. 235 - 238

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 右旋香芹酮 在 正丁基锂 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.83h， 以77%的产率得到(S)-3-(prop-1-en-2-yl)-6-methyl-1,5-cyclohexadienyl trimethylsilyl ether
  参考文献：
  名称：

  Highly Potent Activity of (1R,2R,6S)-3-Methyl-6-(prop-1-en-2-yl)cyclohex-3-ene-1,2-diol in Animal Models of Parkinson’s Disease

  摘要：

  (1R,2R,6S)-3-甲基-6-(丙-1-烯-2-基)环己-3-烯-1,2-二醇 1 在 MPTP 和氟哌啶醇动物模型中均表现出强效的抗帕金森症活性。使用化合物 1 能使运动和探索活动几乎完全恢复，其效果与对照药物（左旋多巴）相当。化合物 1 的八个立体异构体均已被合成，且其绝对构型对抗帕金森症活性的影响也已得到验证。

  DOI：

  10.1021/jm2001579

文献信息

• A practical method for regiocontrolled one-carbon ring contraction
  作者：Matthew J. Mitcheltree、Zef A. Konst、Seth B. Herzon

  DOI：10.1016/j.tet.2013.04.027

  日期：2013.7

  A practical and efficient method for the perfluorobutanesulfonyl azide-mediated one-carbon ring contraction of cyclic enoxysilanes is described. High-yielding procedures for the elaboration of the resulting N-acyl sulfonamide products are reported.

  描述了一种实用且有效的方法，用于全氟丁烷磺酰叠氮化物介导的环状环氧硅烷的一碳环收缩。报道了详细的高产程序，用于制备所得的N-酰基磺酰胺产物。
• Intramolecularly Competitive Ireland-Claisen Rearrangements:  Scope and Potential Applications to Natural Product Synthesis
  作者：Sang-phyo Hong、Harriet A. Lindsay、Tripura Yaramasu、Xiaowei Zhang、Matthias C. McIntosh

  DOI：10.1021/jo010752r

  日期：2002.4.1

  A variety of bis-allylic esters were prepared by vinylmetal addition to cycloalkenones followed by esterification either in situ or in a separate operation. For chiral cyclohexenones, the vinyl additions generally occurred with > 10:1 diastereoselectivity. Although in some cases the bis-allylic esters proved to be sensitive to silica gel or other adsorbents, all of the esters examined could be isolated in acceptable purity. The Ireland-Claisen rearrangement of the bis-allylic esters occurred with complete regioselectivity via the exocyclic alkene. The alkene stereochemistry and the stereochemistry at C-2 and C-3 of the pentenoic acid products were consistent with a chairlike transition state in the rearrangement. Substituents at the carbons adjacent to the allylic carbinol carbon (i.e., C-2 or C-6 in cyclohexenone-derived substrates) directed the stereochemical course of the rearrangement. The rearrangements generally proceeded so as to place the larger of the C-2 or C-6 substituents in the pseudoequatorial position with respect to the chairlike transition state. For a bis-allylic ester bearing both a C-2-CH3 and a C-6-OMEM substituent, the rearrangement product resulted from the nominally smaller OMEM substituent occupying a pseudoequatorial position with respect to the chairlike transition state.
• Domino Mukaiyama–Michael reactions in the synthesis of polycyclic systems
  作者：Florence C.E. Sarabèr、Svetlana Dratch、Geke Bosselaar、Ben J.M. Jansen、Aede de Groot

  DOI：10.1016/j.tet.2005.11.059

  日期：2006.2

  Good results were obtained in the Mukaiyama-Michael reaction of the silyl enol ether of cyclohexanone with 2-methyl-2cyclopentenone and carvone, with transfer of the silyl group to the receiving enone and with TrSbCl6 as catalyst. A second Mukaiyama-Michael reaction of this new silyl enol ether with methyl vinyl ketone and cyclization of the resulting adduct leads to tricyclic compounds in one-pot domino sequences. The scope and limitations of this domino reaction have been investigated. (c) 2005 Elsevier Ltd. All rights reserved.