(R)-1-(4-methoxyphenyl)hex-5-en-1-ol | 1172594-99-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (R)-1-(4-methoxyphenyl)hex-5-en-1-ol
• 英文别名: 1-(4-methoxyphenyl)hex-5-en-1-ol；(R) 1-(4-methoxyphenyl)-5-hexen-1-ol；(R) 1-(p-methoxyphenyl)-5-hexen-1-ol；(1R)-1-(4-methoxyphenyl)hex-5-en-1-ol
• CAS: 1172594-99-8
• 化学式: C₁₃H₁₈O₂
• 分子量: 206.285
• InChiKey: KYFPOLSETNDVKY-CYBMUJFWSA-N

物化性质

• 沸点：
  332.0±42.0 °C(Predicted)
• 密度：
  1.003±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-1-(4-methoxyphenyl)hex-5-en-1-ol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 甲醇 、 sodium tetrahydroborate 作用下， 以 二氯甲烷 为溶剂， 反应 13.5h， 生成 (+)-centrolobine
  参考文献：
  名称：

  A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

  摘要：

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.005
• 作为产物：
  描述：

  乙基5-(4-甲氧基苯基)-5-氧代戊酸酯 在 咪唑 、 4-二甲氨基吡啶 、 Noyori's catalyst 、 甲酸 、 potassium tert-butylate 、 四丁基氟化铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.5h， 生成 (R)-1-(4-methoxyphenyl)hex-5-en-1-ol
  参考文献：
  名称：

  A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps

  摘要：

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.01.005

文献信息

• Stereoselective Synthesis of Cyclic Ethers via the Palladium-Catalyzed Intramolecular Addition of Alcohols to Phosphono Allylic Carbonates
  作者：Anyu He、Nongnuch Sutivisedsak、Christopher D. Spilling

  DOI：10.1021/ol900980s

  日期：2009.7.16

  Cross metathesis of the acrolein-derived phosphono allylic carbonate and hydroxy alkenes using second generation Grubbs catalyst and copper(I) iodide gave the substituted phosphonates in good yield. Stereospecific palladium(0)-catalyzed cyclization gave tetrahydrofuran and tetrahydropyran vinyl phosphonates. Regioselective Wacker oxidation of the vinyl phosphonate gave the β-keto phosphonate, which

  使用第二代格鲁布斯催化剂和碘化铜(I)对丙烯醛衍生的膦酰基烯丙碳酸酯和羟基烯烃进行交叉复分解，以良好的收率得到取代的膦酸酯。立体定向钯(0) 催化环化得到四氢呋喃和四氢吡喃乙烯基膦酸酯。乙烯基膦酸酯的区域选择性瓦克氧化得到 β-酮基膦酸酯，其与苯甲醛进行 HWE 反应，生成不饱和酮。 centrolobine 的正式合成进一步证明了交叉复分解/环化方案的实用性。
• 10.1021/acs.orglett.4c01969
  作者：Alexandridis, Anestis、Rancon, Thibault、Halliday, Abigail、Kochem, Amélie、Quintard, Adrien

  DOI：10.1021/acs.orglett.4c01969

  日期：——

  newly formed stereocenters. When iron-catalyzed borrowing hydrogen from allylic alcohols was combined with a stereocontrolled organocatalytic oxa-Michael addition, a wide array of chiral tetrahydropyrans were efficiently prepared. The reaction could be performed in a diastereoselective manner from pre-existing stereocenters or enantioselectively from achiral substrates. The key to success was the reactivity

  立体控制的 oxa-Michael 加成具有挑战性，因为该过程具有高度可逆性，最终导致新形成的立体中心外消旋化。当铁催化的烯丙醇借氢与立体控制的有机催化氧杂迈克尔加成相结合时，可以有效地制备多种手性四氢吡喃。该反应可以以非对映选择性方式从预先存在的立体中心进行或以对映选择性方式从非手性底物进行。成功的关键是铁络合物的反应活性，它对烯丙醇脱氢具有选择性，并不可逆地导致反应生成最终产物。
• A flexible enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A using asymmetric transfer hydrogenation/tandem Grubbs cross-metathesis/oxy-Michael reaction as key steps
  作者：Gullapalli Kumaraswamy、Dasa Rambabu

  DOI：10.1016/j.tetasy.2013.01.005

  日期：2013.2

  An efficient enantioselective synthesis of (+)-centrolobine and 5-epi-diospongin-A was achieved by the use of asymmetric transfer hydrogenation (ATH)/tandem Grubbs cross-metathesis/oxy-Michael reaction. Furthermore, this strategy allows for diastereodivergent access to every representative member of the family. (C) 2013 Elsevier Ltd. All rights reserved.