外消旋-1-(3-苄基氧基苯基)-1-丙醇 | 49646-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 外消旋-1-(3-苄基氧基苯基)-1-丙醇
• 中文别名: rac-1-(3-苄氧基苯基)-1-丙醇
• 英文名称: 1-(3-(benzyloxy)phenyl)propan-1-ol
• 英文别名: rac-1-(3-Benzyloxyphenyl)-1-propanol；1-(3-phenylmethoxyphenyl)propan-1-ol
• CAS: 49646-55-1
• 化学式: C₁₆H₁₈O₂
• 分子量: 242.318
• InChiKey: WSOZXYQVQZECKM-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于丙酮、二氯甲烷

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：

  外消旋-1-(3-苄基氧基苯基)-1-丙醇 在 对甲苯磺酸 、 二甲基亚砜 、 三乙胺 、 原甲酸三乙酯 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 2-(3-Benzyloxy-phenyl)-2-ethyl-[1,3]dioxolane
  参考文献：
  名称：

  Studies of the New Herbicide KIH-6127. Part II. Synthesis and Herbicidal Activity of 6-Acyl Pyrimidin-2-yl Salicylates and Analogues against Barnyard Grass

  摘要：

  The method reported previously (Part I) was employed to prepare a variety of novel 6-acylsalicylates as key intermediates. 6-Acylpyrimidin-2-yl salicylates (2-acyl-6-[(4,6-disubstituted pyrimidin-2-yl)oxy]benzoate derivatives: Type 1), the closely related phthalide compounds (3-alkyl-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]phthalide derivatives: Type 2) and the ketal derivatives of 2-acyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoates (Type 3) were synthesized and their herbicidal activities measured. Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate gave excellent control of barnyard grass with a promising profile as a prototype rice herbicide.

  DOI：

  10.1002/(sici)1096-9063(199608)47:4<327::aid-ps432>3.0.co;2-u
• 作为产物：
  描述：

  溴乙烷 、 3-苄氧基苯甲醛 在 magnesium 作用下， 以 乙醚 为溶剂， 生成 外消旋-1-(3-苄基氧基苯基)-1-丙醇
  参考文献：
  名称：

  Studies of the New Herbicide KIH-6127. Part II. Synthesis and Herbicidal Activity of 6-Acyl Pyrimidin-2-yl Salicylates and Analogues against Barnyard Grass

  摘要：

  The method reported previously (Part I) was employed to prepare a variety of novel 6-acylsalicylates as key intermediates. 6-Acylpyrimidin-2-yl salicylates (2-acyl-6-[(4,6-disubstituted pyrimidin-2-yl)oxy]benzoate derivatives: Type 1), the closely related phthalide compounds (3-alkyl-7-[(4,6-dimethoxypyrimidin-2-yl)oxy]phthalide derivatives: Type 2) and the ketal derivatives of 2-acyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoates (Type 3) were synthesized and their herbicidal activities measured. Methyl 2-acetyl-6-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate gave excellent control of barnyard grass with a promising profile as a prototype rice herbicide.

  DOI：

  10.1002/(sici)1096-9063(199608)47:4<327::aid-ps432>3.0.co;2-u

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。
• 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％）。
• Catalytic Enantioselective Cross-Couplings of Secondary Alkyl Electrophiles with Secondary Alkylmetal Nucleophiles: Negishi Reactions of Racemic Benzylic Bromides with Achiral Alkylzinc Reagents
  作者：Jörg T. Binder、Christopher J. Cordier、Gregory C. Fu

  DOI：10.1021/ja308460z

  日期：2012.10.17

  We have developed a nickel-catalyzed method for the asymmetric cross-coupling of secondary electrophiles with secondary nucleophiles, specifically, stereoconvergent Negishi reactions of racemic benzylic bromides with achiral cycloalkylzinc reagents. In contrast to most previous studies of enantioselective Negishi cross-couplings, tridentate pybox ligands are ineffective in this process; however, a

  我们开发了一种镍催化的方法，用于二级亲电试剂与二级亲核试剂的不对称交叉偶联，特别是外消旋苄基溴与非手性环烷基锌试剂的立体聚合 Negishi 反应。与之前大多数对映选择性 Negishi 交叉偶联的研究相比，三齿 pybox 配体在此过程中无效；然而，一种新的、易于获得的双齿异喹啉-恶唑啉配体提供了出色的 ee 和良好的产率。使用无环烷基锌试剂作为偶联伙伴导致发现了一种非常不寻常的异构化，该异构化可从未支化的亲核试剂中产生大量的支化交叉偶联产物。
• Spiroketal-based C2-symmetric scaffold for asymmetric catalysis
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US10565015B2

  公开（公告）日：2020-02-18

  Provided herein is a compound of formula (I): wherein each R is independently selected from the group consisting of C1-8 alkyl, C1-8 heteroalkyl having 1-4 heteroatoms independently selected from N, O, and S, C3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S, C6-10 aryl, and 5-10 membered heteroaryl having 1-4 heteroatoms independently selected from N, O, and S; each X is independently selected from OH, PAr2, P(O)Ar2, OPAr2, C3-6 cycloalkyl, 3-10 membered heterocycloalkyl having 1-4 heteroatoms independently selected from N, O, and S or each X together form O2PNR′2; Ar is C6-10aryl; and each R′ is independently selected from hydrogen and C1-8 alkyl. Also provided are methods of making and using the compound of formula (I).

  本文提供的是式 (I) 化合物： 其中每个 R 独立选自由 N、O 和 S 组成的 C1-8 烷基、具有 1-4 个杂原子的 C1-8 杂烷基、具有 1-4 个杂原子的 C3-6 环烷基、具有 1-4 个杂原子的 3-10 分子杂环烷基、具有 1-4 个杂原子的 C6-10 芳基和具有 1-4 个杂原子的 5-10 分子杂芳基；每个 X 独立选自 OH、PAr2、P(O)Ar2、OPAr2、C3-6 环烷基、具有 1-4 个独立选自 N、O 和 S 的杂原子的 3-10 分子杂环烷基或每个 X 共同形成 O2PNR′2；Ar 为 C6-10 芳基；且每个 R′独立选自氢和 C1-8 烷基。还提供了制造和使用式(I)化合物的方法。
• Agents acting on the central nervous system. 19. (+-)-1-(o- and m-Alkanoylphenoxy)-3-(N4-arylpiperazinyl)propan-2-ols as local anesthetics, hypotensives, and tranquilizers
  作者：Shri N. Rastogi、Nitya Anand、P. P. Gupta、J. N. Sharma

  DOI：10.1021/jm00265a012

  日期：1973.7