(S)-1-(3-(benzyloxy)phenyl)propan-1-ol

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-1-(3-(benzyloxy)phenyl)propan-1-ol
• 英文别名: (1S)-1-(3-phenylmethoxyphenyl)propan-1-ol
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: WSOZXYQVQZECKM-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  (S)-1-(3-(benzyloxy)phenyl)propan-1-ol 在 正丁基锂 、 palladium on activated charcoal 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 23.5h， 生成 (1R,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diol 、 (1S,3S,3'S)-3,3'-diethyl-3H,3'H-1,1'-spirobi[isobenzofuran]-7,7'-diol
  参考文献：
  名称：

  过渡金属催化中手性C2对称的含螺氧基的配体的设计，合成及应用

  摘要：

  我们提出了一种方便，经济的途径，可开发出一种新的基于spiroketal的C 2对称手性支架，称为SPIROL。基于该螺环支架，产生了几种手性配体。这些配体已成功用于一系列立体选择性转化中，包括铱催化的氢芳基化（高达95％ee），钯催化的烯丙基烷基化（高达97％ee），分子间钯催化的Heck偶联（高达94％）。ee）和铑催化的脱氢丙氨酸加氢反应（最高ee达93％）。

  DOI：

  10.1002/anie.201713304
• 作为产物：
  描述：

  氯化苄 在 diphenyl((R)-1-((S)-1-phenylethyl)aziridin-2-yl)methanol 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.0h， 生成 (S)-1-(3-(benzyloxy)phenyl)propan-1-ol
  参考文献：
  名称：

  过渡金属催化中手性C2对称的含螺氧基的配体的设计，合成及应用

  摘要：

  我们提出了一种方便，经济的途径，可开发出一种新的基于spiroketal的C 2对称手性支架，称为SPIROL。基于该螺环支架，产生了几种手性配体。这些配体已成功用于一系列立体选择性转化中，包括铱催化的氢芳基化（高达95％ee），钯催化的烯丙基烷基化（高达97％ee），分子间钯催化的Heck偶联（高达94％）。ee）和铑催化的脱氢丙氨酸加氢反应（最高ee达93％）。

  DOI：

  10.1002/anie.201713304

文献信息

• Spiroketal-Based C2-Symmetric Scaffold For Asymmetric Catalysis
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20190084995A1

  公开（公告）日：2019-03-21

  Provided herein is a compound of formula (I): wherein each R is independently selected from the group consisting of C 1-8 alkyl, C 1-8 heteroalkyl having 1-4 heteroatoms independently selected from N, O, and S, C 3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S, C 6-10 aryl, and 5-10 membered heteroaryl having 1-4 heteroatoms independently selected from N, O, and S; each X is independently selected from OH, PAr 2 , P(O)Ar 2 , OPAr 2 , C 3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S or each X together form O 2 PNR′ 2 ; Ar is C 6-10 aryl; and each R′ is independently selected from hydrogen and C 1-8 alkyl. Also provided are methods of making and using the compound of formula (I).

  本文提供的是一种化合物，其化学式为（I）：其中每个R独立地选自以下组合：C1-8烷基，具有1-4个杂原子（N、O和S）的C1-8杂烷基，C3-6环烷基，具有1-4个杂原子（N、O和S）的3-10环杂烷基，C6-10芳基，具有1-4个杂原子（N、O和S）的5-10杂芳基；每个X独立地选自OH、PAr2、P(O)Ar2、OPAr2、C3-6环烷基，具有1-4个杂原子（N、O和S）的3-10环杂烷基，或每个X一起形成O2PNR′2；Ar为C6-10芳基；每个R′独立地选自氢和C1-8烷基。还提供了制备和使用化合物（I）的方法。
• Chiral diphenylselenophosphoramides: a new class of chiral ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes
  作者：Min Shi、Wen-Sheng Sui

  DOI：10.1016/s0957-4166(00)00016-1

  日期：2000.2

  Chiral C-2-symmetric diphenylselenophosphoramides 1 and 2 were prepared from the reaction of diphenylselenophosphinic chloride with(1R,2R)-(-)-1,2-diaminocyclohexane and(1R,2R)-(+)-1,2-diphenylethylenediamine, respectively, in high yields. Another novel chiral ligand 3 was prepared from the reaction of diphenylselenophosphinic chloride with (R)-(+)-1,1'-binaphthyl-2,2'-diamine using butyllithium as the base. The ligands were used as catalytic chiral ligands in the titanium(IV) alkoxide-promoted enantioselective addition reaction of diethylzinc to aldehydes. (C) 2000 Elsevier Science Ltd, All rights reserved.
• C2-Symmetric diphenylphosphoramide and diphenylthiophosphoramide derived from (1R,2R)-1,2-diaminocyclohexane as ligands for the titanium(IV) alkoxide-promoted addition of diethylzinc to aldehydes
  作者：Min Shi、Wen-Sheng Sui

  DOI：10.1016/s0957-4166(99)00348-1

  日期：1999.8

  Chiral C-2-symmetric diphenylphosphoramide 4 and diphenylthiophosphoramide 5 were prepared from the reaction of diphenylphosphinic chloride and diphenylthiophosphinic chloride with (1R,2R)-(-)-1,2-diaminocyclohexane in the presence of diisopropylethylamine in high yields. They were used as chiral ligands in the catalytic asymmetric addition reaction of diethylzinc to aldehydes in the presence of titanium(IV) isopropoxide to give the corresponding sec-alcohols in 70-83% ee with an (R)-configuration and in 40-50% ee with an (S)-configuration, respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Enantioselective addition of diethylzinc to aromatic aldehydes catalyzed by Ti(IV) complexes of C2-symmetrical chiral BINOL derivatives
  作者：Shaohua Gou、Zaher M.A. Judeh

  DOI：10.1016/j.tetlet.2008.10.149

  日期：2009.1

  Enantioselective addition of diethylzinc to a series of aromatic aldehydes is developed using new chiral C2-symmetric ligand (S)-2,2'-(1,1'-binaphthyl-2,2'-diylbis(oxy))bis(methylene)bis(4-nitrophenol) (S)-2b. The catalytic system employing 10 mol % of (S)-2b and 120 mot %. of Ti(OiPr)(4) was found to promote the addition of diethylzinc to a wide range of aromatic aldehydes with electron-donating and electron-withdrawing substituents, giving up to 89% ee and up to 95% yield of the corresponding secondary alcohol under mild conditions. (C) 2008 Elsevier Ltd. All rights reserved.
• Design, Synthesis, and Application of Chiral <i>C</i> ₂ ‐Symmetric Spiroketal‐Containing Ligands in Transition‐Metal Catalysis
  作者：Alonso J. Argüelles、Siyuan Sun、Brenna G. Budaitis、Pavel Nagorny

  DOI：10.1002/anie.201713304

  日期：2018.5.4

  We present an expedient and economical route to a new spiroketal‐based C2‐symmetric chiral scaffold, termed SPIROL. Based on this spirocyclic scaffold, several chiral ligands were generated. These ligands were successfully employed in an array of stereoselective transformations, including in iridium‐catalyzed hydroarylations (up to 95 % ee), palladium‐catalyzed allylic alkylations (up to 97 % ee),

  我们提出了一种方便，经济的途径，可开发出一种新的基于spiroketal的C 2对称手性支架，称为SPIROL。基于该螺环支架，产生了几种手性配体。这些配体已成功用于一系列立体选择性转化中，包括铱催化的氢芳基化（高达95％ee），钯催化的烯丙基烷基化（高达97％ee），分子间钯催化的Heck偶联（高达94％）。ee）和铑催化的脱氢丙氨酸加氢反应（最高ee达93％）。