(R)-1-(3-甲氧基苯基)-1-戊醇 | 1014692-51-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: (R)-1-(3-甲氧基苯基)-1-戊醇
• 英文名称: (R)-1-(3-methoxyphenyl)-1-pentanol
• 英文别名: (R)-1-(3-methoxyphenyl)pentan-1-ol；(1R)-1-(3-methoxyphenyl)pentan-1-ol
• CAS: 1014692-51-3
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: GYVGGGCDYOKNNU-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  甲氧基-三氟甲基苯 、 (R)-1-(3-甲氧基苯基)-1-戊醇 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 0.5h， 生成 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-(3-methoxy-phenyl)-pentyl ester
  参考文献：
  名称：

  Ti-TADDOLate-catalyzed, highly enantioselective addition of alkyl- and aryl-titanum derivatives to aldehydes

  摘要：

  Toluene-ether or toluene-hexane solutions of aryl and alkyl triisopropoxy titanium reagents (free of Li, Mg, or Zn salts) are prepared from the corresponding Li or Grignard reagents and ClTi((OPr)-Pr-i)(3), with careful removal of salts (centrifugation of LiCl or of dioxane.MgX(2), and addition of 12-crown-4). The solutions of the organotitanium compounds are combined with one equiv. of an aldehyde and 0.2 equiv. of (R,R)-diisopropoxy-(alpha,alpha,alpha',alpha'-tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanolato) titanium (Ti-TADDOLate 3) at dry-ice temperature. Warming up to room temperature leads to nucleophilic addition to the (Si)-face of the aldehydes with enantioselectivities as high as 99.5 : 0.5 (products 4 - 33 in Scheme 4). Functional groups or protecting groups and branching in the Ti-R group and in the aldehyde must be remote from the reacting centers. Aryl groups can be added to aldehydes by this method. - In contrast to all the enantioselective R(2)Zn additions to aldehydes, in which only one R-group is actually transferred, a twice as economic use is made of the originally employed R-metal reagent in the method described here. - A procedure for multigram preparation of the spiro-Ti-TADDOLate (2) employed for the in situ generation of the catalyst (3) is described, and details of the determination of enantiomer ratios (er) by GC and NMR methods are given (Tab. 2, 3). The mechanistic interpretation of Ti-TADDOLate-mediated nucleophilic additions as derived previously (ref.(4e)) is also compatible with this monometallic variant of the method.

  DOI：

  10.1016/s0040-4020(01)90475-2
• 作为产物：
  描述：

  BUTYLZINC BROMIDE 、 3-甲氧基苯甲醛 在 titanium(IV) isopropylate 、 magnesium bromide 、 (R)-3-(3,5-diphenylphenyl)-2,2'-dihydroxy-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 3.17h， 以82%的产率得到(R)-1-(3-甲氧基苯基)-1-戊醇
  参考文献：
  名称：

  有机卤化锌试剂催化醛的对映选择性烷基化

  摘要：

  在[Ti（O i Pr）4 ]和MgBr 2存在下，使用衍生自H 8-联萘酚衍生物的钛（IV）催化剂，可以将官能化的烷基卤化锌用于醛的对映选择性加成反应。在本反应中可以耐受多种官能团，包括烯烃，氯原子，受保护的醇，酰胺和氰基，从而以高收率和对映选择性提供相应的官能化醇（参见方案）。

  DOI：

  10.1002/chem.201204346

文献信息

• Catalytic Enantioselective Alkylation and Arylation of Aldehydes by Using Grignard Reagents
  作者：Yusuke Muramatsu、Shinichi Kanehira、Masato Tanigawa、Yuta Miyawaki、Toshiro Harada

  DOI：10.1246/bcsj.20090232

  日期：2010.1.15

  the resulting mixed titanium reagents undergo addition to aldehydes with high enantioselectivities (typically >90% ee) and high yields. The method is applicable to various combination of aldehydes (R 1 CHO; R 1 = aryl, heteroaryl, 1-alkenyl, and alkyl) and Grignard reagents (R 2 MgX; R 2 = primary alkyl and aryl). Thus, a variety of enantiomerically enriched secondary alcohols (R 1 CH*(OH)R 2 ) can

  我们开发了一种有效且实用的方法，通过使用格氏试剂与四异丙醇钛的组合，对醛进行催化对映选择性烷基化和芳基化。格氏试剂和四异丙醇钛以约 1 的摩尔比混合。1:2。在由 BINOL 配体 4a 和 4b 以及四异丙醇钛原位形成的催化剂（2-4 mol%）存在下，所得混合钛试剂以高对映选择性（通常 >90% ee）和高产量。该方法适用于醛（R 1 CHO；R 1 = 芳基、杂芳基、1-烯基和烷基）和格氏试剂（R 2 MgX；R 2 = 伯烷基和芳基）的各种组合。因此，可以制备多种对映体富集的仲醇(R 1 CH*(OH)R 2 )。也已经证明可以使用官能化的芳基格氏试剂来生成高度官能化的二芳基甲醇。该方法的制备效用已通过以下事实表明：反应操作简单，可以毫无困难地在 10 毫摩尔规模上进行，并且配体可以很容易地回收。
• Ru/Me-BIPAM-Catalyzed Asymmetric Addition of Arylboronic Acids to Aliphatic Aldehydes and α-Ketoesters
  作者：Yasunori Yamamoto、Tomohiko Shirai、Momoko Watanabe、Kazunori Kurihara、Norio Miyaura

  DOI：10.3390/molecules16065020

  日期：——

  A ruthenium-catalyzed asymmetric arylation of aliphatic aldehydes and α-ketoesters with arylboronic acids has been developed, giving chiral alkyl(aryl)methanols and α-hydroxy esters in good yields. The use of a chiral bidentate phosphoramidite ligand (Me-BIPAM) achieved excellent enantioselectivities.

  已经开发了钌催化的脂肪醛和α-酮酯与芳基硼酸的不对称芳基化，以良好的产率得到手性烷基（芳基）甲醇和α-羟基酯。手性双齿亚磷酰胺配体 (Me-BIPAM) 的使用实现了出色的对映选择性。
• Catalytic Asymmetric Alkylation of Aldehydes with Grignard Reagents
  作者：Yusuke Muramatsu、Toshiro Harada

  DOI：10.1002/anie.200704963

  日期：2008.1.25