(E)-(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propenol | 112497-26-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (E)-(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propenol
• 英文别名: (E)-1-cyclohexyl-3-trimethylsilylprop-2-en-1-ol
• CAS: 112497-26-4
• 化学式: C₁₂H₂₄OSi
• 分子量: 212.407
• InChiKey: PLLJZWSHHLCAMC-MDZDMXLPSA-N

物化性质

• 沸点：
  270.0±15.0 °C(Predicted)
• 密度：
  0.904±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (E)-(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propenol 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 锂硼氢 、 草酰氯 、 L-(+)-酒石酸二异丙酯 、 4 A molecular sieve 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 19.58h， 生成 (1R,2S)-(+)-1-cyclohexyl-1-(4-fluorophenyl)-3-(trimethylsilyl)propane-1,2-diol
  参考文献：
  名称：

  Anticholinergic Agents. 4. Stereocontrolled Synthesis of Fluorinated Acetylcholine Antagonists; Syntheses of the Two 1-Cyclohexyl-1-(4-fluorophenyl)-3-piperidyl-1-propanols and their Methiodides.

  摘要：

  Four new putative muscarinic antagonists, (R)-(-)- and (S)-(+)-1-cyclohexyl-1-(4-fluorophenyl)-3-piperidyl-1-propanol and their methiodides, have been synthesised. Absolute configurations have been assigned on the basis of the anticipated chirality of the products of the Sharpless asymmetric epoxidation reaction.

  DOI：

  10.3891/acta.chem.scand.47-1019
• 作为产物：
  描述：

  1-cyclohexyl-3-(trimethylsilyl)prop-2-yn-1-ol 在 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 16.0h， 以86%的产率得到(E)-(+/-)-1-cyclohexyl-3-(trimethylsilyl)-2-propenol
  参考文献：
  名称：

  Anticholinergic Agents. 4. Stereocontrolled Synthesis of Fluorinated Acetylcholine Antagonists; Syntheses of the Two 1-Cyclohexyl-1-(4-fluorophenyl)-3-piperidyl-1-propanols and their Methiodides.

  摘要：

  Four new putative muscarinic antagonists, (R)-(-)- and (S)-(+)-1-cyclohexyl-1-(4-fluorophenyl)-3-piperidyl-1-propanol and their methiodides, have been synthesised. Absolute configurations have been assigned on the basis of the anticipated chirality of the products of the Sharpless asymmetric epoxidation reaction.

  DOI：

  10.3891/acta.chem.scand.47-1019

文献信息

• A regiodefined synthesis of α-trimethylsilyl ketones catalyzed by rhodium(I) hydride complex
  作者：Susumu Sato、Isamu Matsuda、Yusuke Izumi

  DOI：10.1016/0022-328x(88)80214-6

  日期：1988.4

  Regiodefined synthesis of α-trimethylsilyl ketones is attained by one of three different routes: isomerization of β-trimethylsilyl allyl alcohols (route A), isomerization of β′-trimethylsilyl allyl alcohols (route B), and dehydrogenation of β-trimethylsilyl alcohols via transfer hydrogenation to α,β-enones (route C). All of these procedures are catalyzed efficiently by HRh(PPh3)4 at about 100 °C. Route

  通过以下三种途径之一实现区域定义的α-三甲基硅烷基酮的合成：β-三甲基硅烷基烯丙醇的异构化（途径A），β'-三甲基硅烷基烯丙醇的异构化（途径B）和β-三甲基硅烷基醇通过转移脱氢氢化成α，β-烯酮（路线C）。所有这些步骤均在大约100°C下被HRh（PPh 3）4有效地催化。路线A不可避免地需要存在2-三甲基甲硅烷基-1-苯基-2-丙烯-1-酮作为平滑异构化的助催化剂。这有力地表明，一种分子间转移氢化在催化循环中起着重要的作用。
• A versatile route to silylsubstituted ketones by rhodium catalyzed isomerization of silylated allyl alcohols
  作者：Susumu Sato、Hisashi Okada、Isamu Matsuda、Yusuke Izumi

  DOI：10.1016/s0040-4039(01)80021-6

  日期：1984.1

  The rhodium catalyzed isomerization of α-, β-, and γ-silylated allyl alcohols has been successfully applied to the selective synthesis of acylsilane, α-silyl ketones, and β-silyl ketones, respectively.

  铑催化的α-，β-和γ-甲硅烷基化烯丙醇的异构化已分别成功地分别用于酰基硅烷，α-甲硅烷基酮和β-甲硅烷基酮的选择性合成。
• Nickel-catalyzed coupling reaction of sterically congested cis bromides and lithium alkenylborates
  作者：Yuichi Kobayashi、Yuji Nakayama、Ryo Mizojiri

  DOI：10.1016/s0040-4020(97)10206-x

  日期：1998.2

  Lithium alkenyl borates of general structure 5 (RT=alkenyl) couple with cis bromides 1 at room temperature overnight in the presence of NiCl2(PPh3)2 as a catalyst to furnish dienes of general structure 3 with retention of the olefin geometries present in both coupling partners. By using this reaction, cis, trans dienes 3 (R=TBDMS, TES, TBDPS; R1=n-C5H11, c-C6H11, R2=H; R3=n-C5H11, Ph) and cis,cis diene

  通式5的烯基硼酸锂（R T =烯基）在室温下在作为催化剂的NiCl 2（PPh 3）2存在下与顺式溴化物1偶联过夜，以提供通式3的二烯并保留存在的烯烃几何结构在两个耦合伙伴中。通过使用该反应，顺式，二烯3（R ＝ TBDMS，TES，TBDPS； R 1＝n -C 5 H 11，c -C 6 H 11，R 2＝ H； R3 = n -C 5 H 11，Ph）和顺式，顺式二烯3（R = TBDMS； R 1 = R 2 = n -C 5 H 11； R 3 = H）以高收率合成。
• Stereoselective synthesis of (2,4)-dien-1-ols; key intermidiates for synthesis of sex pheromones of silk worm and of grape vine moth
  作者：Satoru Kuroda、Tsutomu Katsuki、Masaru Yamaguchi

  DOI：10.1016/s0040-4039(01)80994-1

  日期：1987.1
• Diastereoselectivity in the hydroxyl-directed cyclopropanation of vinylorganometallic compounds
  作者：Mark Lautens、Patrick H. M. Delanghe

  DOI：10.1021/jo00029a004

  日期：1992.1

  Olefins bearing silicon and/or tin substituents undergo highly diastereoselective cyclopropanation in the presence of Sm/CH2I2. The stereochemistry of the tin moiety has a dramatic effect on the rate of a subsequent transmetalation with MeLi.