(S)-1-(2-methoxyphenyl)but-3-en-1-ol | 24165-67-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-1-(2-methoxyphenyl)but-3-en-1-ol
• 英文别名: (S)-(-)-1-(2’-methoxyphenyl)but-3-en-1-ol；(S)-(-)-1-(2-methoxyphenyl)-but-3-en-1-ol；(S)-1-(2-methoxyphenyl)-3-buten-1-ol；1-(2-methoxyphenyl)-3-buten-1-ol；1-(2-methoxyphenyl)but-3-en-1-ol；(1S)-1-(2-methoxyphenyl)but-3-en-1-ol
• CAS: 24165-67-1；27693-90-9；104974-15-4
• 化学式: C₁₁H₁₄O₂
• 分子量: 178.231
• InChiKey: VWOGPWOUPIUOFK-JTQLQIEISA-N

物化性质

• 沸点：
  370 °C(lit.)
• 密度：
  1.032 g/mL at 25 °C(lit.)
• 闪点：
  >230 °F

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• WGK Germany：
  3
• 海关编码：
  2909499000

反应信息

• 作为产物：
  描述：

  烯丙基三丁基锡 、 邻甲氧基苯甲醛 在 C₄₀H₃₉Cl₂N₄ORh 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以82%的产率得到(S)-1-(2-methoxyphenyl)but-3-en-1-ol
  参考文献：
  名称：

  手性双（咪唑啉基）苯基NCN钳形铑（III）催化剂，用于醛的对映选择性烯丙基化和三氟丙酮酸盐的羰基-烯反应

  摘要：

  发现具有双（咪唑啉基）苯基配体的手性NCN钳形铑（III）配合物是有效的催化剂，用于将各种电子和结构不同的醛与烯丙基三丁基锡进行烯丙基化，从而以高收率得到相应的光学活性均烯醇，且对映选择性高达到97％ee。这些配合物还用于三氟丙酮酸乙酯或三氟丙酮酸甲酯与各种2-芳基丙烯的羰基-烯反应中。借助三氟甲磺酸银，钳型铑（III）催化剂可以催化反应，以高收率和高立体选择性（最高95％ee）提供相应的手性α-羟基-α-三氟甲基酯。

  DOI：

  10.1021/jo4014194

文献信息

• Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: computational rationale for enantioselectivity
  作者：Debashis Ghosh、Debashis Sahu、S. Saravanan、Sayed H. R. Abdi、Bishwajit Ganguly、Noor-ul H. Khan、Rukhsana I. Kureshy、Hari C. Bajaj

  DOI：10.1039/c3ob27513b

  日期：——

  A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%) and high enantioselectivity (up to 99%). The experimental results and DFT calculations suggest that para substituted aromatic aldehydes as substrate show higher ee in the product than their ortho/meta counterparts. The 1H and 13C NMR spectra study corroborated the calculated results. The chiral organocatalyst can be easily synthesized from optically pure phenylalanine in two simple steps with 90% overall yield.

  开发了一种由苯丙氨酸衍生的手性酰胺，它作为有效的有机催化剂，用于烯丙基三氯硅烷与芳基、杂芳基和α,β-不饱和醛的反应，以良好的产率（高达90%）和高对映选择性（高达99%）得到所需的同烯丙基醇。实验结果和DFT计算表明，与邻/间位取代的芳香醛相比，对位取代的芳香醛作为底物在产物中显示出更高的对映体过量值。1H和13C NMR光谱学研究证实了计算结果。手性有机催化剂可以通过两个简单步骤从光学纯苯丙氨酸轻松合成，总产率为90%。
• Conformationally Rigid Chiral Pyridine N-Oxides as Organocatalyst: Asymmetric Allylation of Aldehydes
  作者：Elumalai Gnanamani、Nagamalla Someshwar、Chinnasamy Ramaraj Ramanathan

  DOI：10.1002/adsc.201200115

  日期：2012.8.13

  unit with a conformationally rigid chiral backbone has been designed and synthesized in an enantiomerically pure form to utilize in the Lewis base-catalyzed Sakurai–Hosomi–Denmark-type allylation reaction. The chiral pyridine N-oxide in 1:1 mixture of chloroform and 1,1,2,2-tetrachloroethane produced the homoallylic alcohols in up to 98% yield and up to 94% ee.

  具有构象刚性手性骨架的吡啶单元已被设计和合成为对映体纯形式，可用于Lewis碱催化的Sakurai–Hosomi–Denmark型烯丙基化反应。在氯仿和1,1,2,2-四氯乙烷1：1混合物中的手性吡啶N-氧化物生成的均烯丙基醇的收率高达98％，ee高达94％。
• A New Class of Chiral Lewis Basic Metal-Free Catalysts for Stereoselective Allylations of Aldehydes
  作者：Maurizio Benaglia、Valentina Simonini、Luca Pignataro、Stefania Guizzetti、Giuseppe Celentano

  DOI：10.1055/s-2008-1072509

  日期：——

  A new class of amine N-oxides derived from trans-2,5-diphenylpyrrolidine were synthesized in enantiomerically pure form and tested as metal-free catalysts in the reaction of aldehydes with allyl(trichloro)silane to afford homoallylic alcohols. The products were obtained in fair to good yields and up to 85% ee. The behavior of structurally different catalysts and the influence of a coordinating unit present in the organocatalyst on controlling the stereochemical efficiency of the reaction were also investigated. Noteworthy a catalyst capable of promoting the allylation of aliphatic aldehydes with an almost unprecedent and unusually high enantioselectivity, up to 85%, was identified.

  一种新型胺N-氧化物类化合物，源自反式-2,5-二苯基吡咯烷，以纯手性形式合成，并测试作为无金属催化剂，在醛与烯丙基（三氯）硅烷反应中，得到同烯丙醇。产物收率尚可至良好，最高可达85% 的对映体过量。研究了结构不同的催化剂行为，以及有机催化剂中存在的配位单元对反应立体化学效率的影响。值得注意的是，发现了一种催化剂，能以几乎前所未有的高度对映选择性（高达85%）促进脂肪醛的烯丙基化反应。
• Aryl tert-butyl sulfoxide-promoted highly enantioselective addition of allyltrichlorosilane to aldehydes
  作者：Peng Wang、Junmin Chen、Linfeng Cun、Jingen Deng、Jin Zhu、Jian Liao

  DOI：10.1039/b909850j

  日期：——

  A series of enantiomerically pure mono- and bis-aryl tert-butyl sulfoxides were synthesised to promote the enantioselective allylation of aldehydes with allyltrichlorosilane. Moderate to good yields and modest to high enantioselectivities were achieved. The absence of nonlinear effect, spacer effect, promoter loading and concentration effect indicate that only one molecule of aryl tert-butyl sulfoxide is involved in the stereodetermining step.

  一系列手性纯的单和双芳基叔丁基亚砜被合成出来，以促进醛与烯丙基三氯硅烷的非对映选择性烯丙基化反应。实现了中等至良好的产率和适中至高的非对映选择性。非线性效应、间隔效应、促进剂加载和浓度效应的缺失表明，在决定立体化学的步骤中，只有一分子芳基叔丁基亚砜参与其中。
• Enantioselective Allylation of Aldehydes Catalyzed by Diastereoisomeric Bis(tetrahydroisoquinoline) N,N′-Dioxides
  作者：Klára Vlašaná、Radim Hrdina、Irena Valterová、Martin Kotora

  DOI：10.1002/ejoc.201001219

  日期：2010.12

  enantioselectivity up to 96 %. On the other hand, the allylation of aromatic aldehydes in the presence of the (R,R ax ,R) catalyst proceeded only in MeCN (up to 67 % ee), and the level of asymmetric induction was strongly influenced by the presence of electron-donating and -accepting groups in the aldehyde. The allylation of α,β-unsaturated aldehydes proceeded only in dichloromethane (enantioselectivity

  在两种非对映异构体 (R,R ax ,R)- 和 (R,S ax ,R)-bis-1,1'-[5,6,7,研究了 8-四氢-3-(四氢呋喃-2-基)异喹啉]N,N'-二氧化物。反应过程受所选溶剂的影响很大。(R,S ax ,R) 催化剂有效地促进了 THF 中的反应，对映选择性高达 96%。另一方面，在 (R,R ax ,R) 催化剂存在下芳香醛的烯丙基化仅在 MeCN（高达 67 % ee）中进行，并且不对称诱导的水平受到电子存在的强烈影响。醛中的供体和受体基团。α,β-不饱和醛的烯丙基化仅在二氯甲烷中进行（对映选择性高达 68%）。